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• WOMEN on WATER (WOW) - REGISTER NOW for the 2025 Sailing Season

  • Start
    24 Jan 2025
  • End
    08 Aug 2025
  • Location
    Capital Cove Marina, Joint Base Anacostia-Bolling (JBAB), 90 Giovannoli Way, Washington, D.C. 20032

  Register

  WOMEN ON WATER (WOW), a Pentagon Sailing Club (PSC) group, provides opportunities for women to sail in a fun, supportive, and learning environment!

  From April through October, WOW meets on select Thursdays (5:30 pm until dusk) and Saturdays or Sundays (starting at 9:00 am) at the Capital Cove Marina on Joint Base Anacostia-Bolling (JBAB) in Washington, D.C., where PSC moors a fleet of Catalina Capri 22s. After each sail, WOW members gather at the marina's waterfront restaurant, The Slip Inn.

  Who: All PSC women are welcome to join!

  When: April through October 2025

  Where: Capital Cove Marina, Joint Base Anacostia-Bolling (JBAB), 90 Giovannoli Way, Washington, D.C. 20032

  Cost: $60 covers the cost of the 2025 sailing season
  

  If you DO NOT have access to JBAB, after completing a PSC membership application, you may apply for DBIDS card. This takes time to process. Without a DBIDS card, you don't have access to the marina. Note: PSC can only sponsor DBIDS cards for active club members.

  Happy Sailing!
  

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• Winter Training: Rules of the Road

  • Start
    15 Mar 2025
  •  
  • End
    05 Apr 2025
  •  
  • Schedule
    2 sessions
  • Location
    Phillips School For Contemporary Education, 7010 Braddock Rd, Annandale, VA 22003
  • Spaces left
    22

  Register

  Winter Training: Rules of the Road

  The Pentagon Sailing Club is excited to announce that we will be offering a comprehensive course on the Nautical Rules of the Road. This essential course is scheduled to begin on Saturday, March 15th, and will be followed by an in-depth review session accompanied by a test on Saturday, April 5th.

  Whether you are just starting out on your sailing adventure, looking to brush up on your skills before the sailing season, or an experienced sailor aiming to pass advanced sailing qualification tests, this course is tailored to suit your needs. This is an incredible opportunity to enhance your nautical knowledge and ensure safe and enjoyable sailing experiences. Join us and take the helm towards becoming a savvy sailor!
  
  

  Instructors: Paul G. and Jonah B.

  
  Course Materials Provided:

  • The One-Minute Guide to the Nautical Rules of the Road (hardcopy; provided at the begining of the class)
  • Navigation Rules and Regulations Handbook (electronic version – PDF; provided prior to class start date)

  
  Location:

  7010 Braddock Rd, Annandale, VA 22003

  
  Members may use one (1) FVSM for this class. Please check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.
  
  

  Should you have any questions, please don't hesitate to contact the Training Commodore. We're here to assist you and ensure your experience is beneficial and informative!

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• Late Breaking Opportunity! Clipper Round the World Yacht Race Presentation - Washington, DC Convention Center (Hall C)

  • Start
    29 Mar 2025
  • End
    30 Mar 2025
  • Location
    Washington Convention Center (Hall C)

  Register

  Ever wondered what it’s like to cross the world’s toughest oceans? Looking for your next big challenge?
  
  Pull up this weekend at the Washington Travel and Adventure Show and hear from Jacqueline Kavanagh. She’s an ocean racer, circumnavigator, and Clipper Race Recruitment Manager. She’s been there, done that, and rocked the foulies, making her the realest person to break it all down for you.
  
  29 - 30 March
  Washington Convention Center (Hall C)
  29 March | 10AM - 5PM
  30 March | 11AM - 4PM
  
  Discovery Talk: 30 March | 3-3:30PM
  FREE VIP Tickets → Registrants will receive a coupon via email
  

  Get your tickets - https://travelshows.com/shows/washingtondc/#

  
  

  Clipper Race on Tour USA | Washington, DC - Clipper Round The World Race

  Clipper Race Discovery Talk – Washington, DC - Hear from Jacqueline Kavanagh on how to join the Clipper 2025-26 Race

  Show details
• Racing - DISC Skippers and Crew Meeting

  • When
    01 Apr 2025
  •  
    6:00 PM - 8:30 PM
  • Location
    TBD - Murphy's or Zoom

  This meeting will open DISC's KISS series of Tuesday night races for the year.  The meeting is mandatory for skippers and optional for crew; it's open to members of the PSC Racing Squadron.

  To participate in this event, remember to sign up on the Racing Sign-Up Sheet.

  For more information, contact the Racing Commodore at racing@pentagonsailing.org.

  Show details
• Racing - PSC Race Training

  • Start
    07 Apr 2025
  •  
  • End
    28 Apr 2025
  •  
  • Schedule
    4 sessions
  • Location
    Capital Cove Marina

  Work on proficiency maneuvers and drills with your fellow racing teammates and warm up for the 2025 racing season!  Plan to work on basic sailing skills, crew coordination, mark rounding, and more.

  To participate in this event, remember to sign up on the Racing Sign-Up Sheet.

  Contact the Racing Commodore at racing@pentagonsailing.org for more information.

  Show details
• Racing - Spring Series

  • Start
    08 Apr 2025
  •  
  • End
    06 May 2025
  •  
  • Schedule
    5 sessions
  • Location
    Capital Cove Marina, Bolling AFB, DC

  These races are part of DISC's Spring Series, and are open to members of the PSC Racing Squadron.  To participate in this event, racing members may sign up on the Racing Sign-Up Sheet.

  For more information, contact the Racing Commodore at racing@pentagonsailing.org.

  Show details
• PSC Spring Splash Party and April Social Meeting

  • When
    13 Apr 2025
  •  
    2:00 PM - 6:00 PM
  • Location
    Murphy's Grand Irish Pub
  • Spaces left
    37

  Register

  Show details
• Advanced Coastal Cruising 4-Day Sail, ASA 106

  • Start
    24 Apr 2025
  •  
    10:00 AM
  • End
    27 Apr 2025
  •  
    5:00 PM
  • Location
    Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
  • Spaces left
    4
  • Registered
    2 registrants

  Register

   

  Coastal Cruising 4-Day Training Sail 

  Boat Name: Adventurer (48' schooner)
  

  Slip: Dock F, Slip 2, Port Annapolis, 7074 Bembe Beach Road, Annapolis, MD 21403

  Skipper: Duncan Hood

  Purpose/Training: A 4-day long trip on the Chesapeake Bay.  This is a training sail designed for people want to achieve ASA 106 and be able to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length in coastal and inland waters, in any conditions.  People who wish to receive the ASA certification must have completed the prerequisite courses and time on the water prior to starting this sail.  There is a significant amount of planning required of students for this event.  Experienced instructor, Duncan Hood, will teach this class on his 48' Schooner Adventurer. Adventurer is a 1984 fore & aft staysail schooner manufactured by Cherubini Yachts in Riverside New Jersey.

  Check back soon for sail plan. Join waitlist if sail sells out. 

  Preference will be given to crew who are obtaining their first ASA 106 certification.

  Certifications:
  ASA 106 certification awarded upon successful completion of this sail and a written test. Pursuance of either certification is not a requirement of participating on this sail.

  Prerequisites for ASA 106: ASA 101, 103, 104, and 105.
  

  Locations:
  Start - Dock F, Slip 2 Port Annapolis, MD

  End - Port Annapolis, MD

  POC: Bay Commodore at baycommodore@pentagonsailing.org

  A maximum of 2 FVSMs may be used for this sail. If you are using an FVSM(s), select the applicable registration type with FVSM(s) option. Check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.  The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

  Registration cost includes charter fees, ASA 106 exam and certification fee. PSC no longer receives a discount on ASA textbooks.  Purchase one directly online.

  
  

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• ASA 101/103 Combined #1 @ Phillips School - Contemporary Education & OTW JBAB

  • Start
    24 Apr 2025
  •  
  • End
    04 May 2025
  •  
  • Schedule
    6 sessions
  • Location
    Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
  • Spaces left
    0

  Join waitlist

  ASA 101/103 Combined #1 [April]

  Never sailed before, or has it been a while? This is the course that will get you started!

  Upon completing this combined course, you can skipper a sloop-rigged keelboat of approximately 20 to 30 feet in length by day in light to moderate winds (up to 20 knots) and sea conditions.  

  Full Details

  Classroom: Phillips School - Contemporary Education, Activity Room, 7010 Braddock Rd., Annandale, VA  22003

  • 101 Classroom Apr. 24 (6:00 PM to 8:30 PM)
  • 103 Classroom May 1 (6:00 PM to 8:30 PM)

  On-the-Water Location: Capital Cove Marina @ Joint Base Anacostia-Bolling
  

  • 101 OTW - Apr. 26 & 27 (8:30 AM to 4:30 PM)
  • 103 OTW - May 3 & 4 (8:30 AM to 4:30 PM

  PSC Members may use up to 2 FVSMs for this class. FVSMs are worth $25.00 each for this class. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing either of these pricing options.

  If you have questions - please get in touch with the Training Commodore at trainingcommodore@pentagonsailing.org.

  P.S. You must be a Pentagon Sailing Member to register for this course. If you are not a member, please head over to https://www.pentagonsailing.org/newmember to start your membership.

  Show details
• ASA 201/203 Instructor Certification

  • Start
    28 Apr 2025
  •  
    9:00 AM
  • End
    30 Apr 2025
  •  
    4:30 PM
  • Location
    22978 McKinleyville Rd, Rock Hall, MD 21661
  • Spaces left
    0

  Join waitlist

  ASA 201/203 Instructor Certification Clinic

  Prerequisites: ASA 101/103 Certification

  Recommendation: It is highly advisable to have a minimum of three years of sailing experience or prior involvement as a primary or assistant instructor on the river.

  This year, in collaboration with the Maryland School of Sailing, we are thrilled to offer the ASA 201/203 certification clinic. This is a wonderful opportunity for you to enhance your instructor capabilities on 30+ft  Island Packets, allowing you to further perfect your sailing skills.

  Priority registration for the ASA 201 and 203 certification courses will be given to members who have generously volunteered their time as instructors and are eager to step into lead instructor roles in our river training program.

  Location:

  • Maryland School of Sailing and Seamanship, 22978 McKinleyville Rd, Rock Hall, MD 21661

  Dates and Times:

  • Start on April 28, and finish on April 30; bring some sheets and covers, you will be able to sleep on the Island Packet boats for the duration of the course (no need for a long commute)
    
    

  Please direct your questions to the Training Commodore

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• ASA-104 Bareboat Cruising Certification

  • Start
    08 May 2025
  •  
    9:00 AM
  • End
    10 May 2025
  •  
    5:00 PM
  • Location
    Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
  • Spaces left
    4

  Register

  ASA 104 Bareboat Cruising Certification (a 3-day, 2-night sail)

  Boat:
  48' Schooner Adventurer

  Skipper:
  Duncan Hood

  This a unique opportunity to gain real sailing experience while earning ASA's 104 Bareboat Cruising certification. Experienced instructor, Duncan Hood, will teach this class on his 48' Schooner Adventurer. Adventurer is a 1984 fore & aft staysail schooner manufactured by Cherubini Yachts in Riverside New Jersey. Duncan has offered to host club members on his boat during this sail and provide ASA 104 training. This three-day, two-night trip will give you more than enough experience to demonstrate confidently all the required skills and knowledge covered by the ASA 104 course so that you can charter a boat.

  Your fee covers ASA certification. PSC no longer gets a discount from ASA for the textbook.  Purchase one online.  Food and drinks on board are the crew's responsibility. 

  Additional information on ASA 104:
  ASA 104, Bareboat Cruising Certification

  Prerequisites:
  ASA requires 101 and 103 certifications before taking the course and recommends a minimum of 80 on-the-water sailing hours.

  Locations:
  Start - Dock F, Slip 2 Port Annapolis, MD

  End - Port Annapolis, MD

  Itinerary: 
  Sail from Port Annapolis and return the next day.

  Notes:
  A maximum of 1 FVSM may be used for this sail. If you use an FVSM, select the applicable ASA 104 with the FVSM payment option. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing this pricing option. The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

  Questions:
  Email Bay Commodore

  PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM

  
  

  Show details
• Racing - Mount Vernon Chase

  • When
    10 May 2025
  •  
    8:30 AM - 5:00 PM
  • Location
    Capital Cove Marina, Joint Base Anacostia–Bolling, District of Columbia

  The Mount Vernon Chase is a pursuit-style race.  Each boat will be given an individual start time, based on PHRF.  Boats will be scored in the order in which they cross the finish line, rather than having times corrected afterwards.  This is a longer race, and it's a great opportunity to see some scenery further from our usual venue.

  This event is open to members of the PSC Racing Squadron; racers, remember to sign up on the Racing Sign-Up Sheet.  For more information, contact the Racing Commodore at racing@pentagonsailing.org.

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• Racing - Summer I Series

  • Start
    13 May 2025
  •  
  • End
    24 Jun 2025
  •  
  • Schedule
    7 sessions
  • Location
    Capital Cove Marina, 90 Giovannoli St, Bolling AFB, DC 20032

  These races are part of DISC's Summer I Series, and are open to members of the PSC Racing Squadron.  Racing Squadron members, remember to sign up on the Racing Sign-Up Sheet.

  For more information, contact the Racing Commodore at racing@pentagonsailing.org.

  Show details
• Close Quarter Maneuvering (ASA 118)

  • When
    17 May 2025
  •  
    9:00 AM - 5:00 PM
  • Location
    Waypoints Annapolis, 222 Severn Ave, Annapolis, MD 21403
  • Spaces left
    2

  Register

  BAY TRAINING DAY SAIL - CLOSE QUARTER MANEUVERING (CQM)

  Boat Name: Dufour 430 - 3 cabin - Epiphany - 2022

  Skipper: Jonah Brewer

  Purpose/Training: This class focuses on teaching students how to safely maneuver a sailboat under power in close quarters in various wind and sea conditions including docking/un-docking, line handling, use of spring lines, backing, turning and holding position in restricted water.  

  You can find the syllabus here.

  Prerequisites: ASA 101/103

  Certifications:
  ASA - ASA 118 (Docking Endorsement) certification awarded upon successful completion of CQM Session and a written test.
  PSC Bay Skipper - Two sails required to fulfill all CQM requirements in the D-CS qualification card.

  POC: baycommodore@pentagonsailing.org

  One FVSM may be used for this sail. If you are using an FVSM, select the Bay Training Day Sail with FVSM payment option. Please check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.

  PSC no longer gets a discount from ASA for the textbook. Purchase one online.

  The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

  Participants are encouraged to join the Bay Skipper Program

  Show details
• Close Quarter Maneuvering (ASA 118)

  • When
    18 May 2025
  •  
    9:00 AM - 5:00 PM
  • Location
    Waypoints Annapolis, 222 Severn Ave, Annapolis, MD 21403
  • Spaces left
    2

  Register

  BAY TRAINING DAY SAIL - CLOSE QUARTER MANEUVERING (CQM)

  Boat Name: Dufour 430 - 3 cabin - Epiphany - 2022

  Skipper: Jonah Brewer

  Purpose/Training: This class focuses on teaching students how to safely maneuver a sailboat under power in close quarters in various wind and sea conditions including docking/un-docking, line handling, use of spring lines, backing, turning and holding position in restricted water.  

  You can find the syllabus here.

  Prerequisites: ASA 101/103

  Certifications:
  ASA - ASA 118 (Docking Endorsement) certification awarded upon successful completion of CQM Session and a written test.
  PSC Bay Skipper - Two sails required to fulfill all CQM requirements in the D-CS qualification card.

  POC: baycommodore@pentagonsailing.org

  One FVSM may be used for this sail. If you are using an FVSM, select the Bay Training Day Sail with FVSM payment option. Please check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.

  PSC no longer gets a discount from ASA for the textbook. Purchase one online.

  The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

  Participants are encouraged to join the Bay Skipper Program

  Show details
• 2025 PSC Memorial Day Raft-Up: Club-Chartered Catamaran

  • Start
    24 May 2025
  •  
    9:00 AM
  • End
    26 May 2025
  •  
    5:00 PM
  • Location
    Waypoints Annapolis, 222 Severn Avenue, Bldg. 15 MD 21403 Annapolis, Maryland
  • Spaces left
    6

  Register

  
  

  2025 PSC Memorial Day Raft-Up: Club-Chartered 47' Catamaran

  • Location: Waypoints Annapolis, 222 Severn Ave, Annapolis, MD 21403 Google maps
  • • Parking space may be limited. Try to carpool.

  REGISTRATION

  • 2025 PSC Memorial Day Raft-Up: Club-Chartered Boat (3-Day Bay Sail) – shared cabin, OR salon

  Miscellaneous costs (fuel, pump-out, dock fees, meals) not included.

  Boat: 47' Catamaran Fountaine Pajot Saona 47 Maestro - 3 + 1 cab. - Dark Star - 2019

  Skipper:  Jonah Brewer email vicecommodore@pentagonsailing.org 

  This is a multi-day social sail over the Memorial Day weekend. We depart the marina on Saturday and meet other boats on the bay, raft-up, and spend the day on the water. See flyer attached below.

  Theme:  SAILING MOVIE TIME 

  Location:

  24 May 2025 - Raft Up will be held in Harness Creek (Coord. N 38° 56.339' / W 076° 30.664'), off South River. CAPT Jonah Brewer will be coordinating the information regarding the raft up itself. Vilma Baez will be planning all of the events. Decorate your S/V with any sailing movie rated “PG”

  25 May 2025 - We will conduct our second event at Herrington Harbor North Marina, (coord. N 38° 46.433' / W 076° 33.867') beginning at 3:00 pm. The event will be catered and cost $22 per person. You will need to bring your own beverage to the event.

  Herrington Harbor North has available slips for the evening of 25 May 2025. Please contact Megan Dierks at 410-867-4343 or make a slip reservation via DOCKWA.

  
  

  This is a great multi-day experience, where you get to experience the liveaboard style, plus you get to raft-up with other boats. The sail is a great time to practice any skills you may need for a certification, or just to make sure you keep them sharp. If all you want is relax, there will be multiple fore-decks where you can do so.

  Monday we return to our home ports.

  We look forward to seeing you. Please pass the information about the Raft Up to anyone who wants to attend and let the skipper know if you have any questions.

  Registration price only covers charter costs. Additional costs such as food, pump-out, fuel, and slip fees will be shared by the crew.

  The charter boat is a catamaran with three 2-person cabins and three singles in salon (sleeping nine). You can check it out here.

  The fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

  POC: Bay Commodore Sumeet C.

  PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM

  Show details
• ASA 101/103 Combined #2 @ Phillips School - Contemporary Education & OTW JBAB

  • Start
    29 May 2025
  •  
  • End
    08 Jun 2025
  •  
  • Schedule
    6 sessions
  • Location
    Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
  • Spaces left
    1

  Register

  ASA 101/103 Combined #2 [May]

  Never sailed before, or has it been a while? This is the course that will get you started!

  Upon completing this combined course, you can skipper a sloop-rigged keelboat of approximately 20 to 30 feet in length by day in light to moderate winds (up to 20 knots) and sea conditions.  

  Full Details

  Classroom: Phillips School - Contemporary Education, Activity Room, 7010 Braddock Rd., Annandale, VA  22003

  • 101 Classroom May 29 (6:00 PM to 8:30 PM)
  • 103 Classroom June 5 (6:00 PM to 8:30 PM)

  On-the-Water Location: Capital Cove Marina @ Joint Base Anacostia-Bolling
  

  • 101 OTW - May 31 & June 1 (8:30 AM to 4:30 PM)
  • 103 OTW - June 7 & 8 (8:30 AM to 4:30 PM

  PSC Members may use up to 2 FVSMs for this class. FVSMs are worth $25.00 each for this class. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing either of these pricing options.

  If you have questions - please get in touch with the Training Commodore at trainingcommodore@pentagonsailing.org.

  P.S. You must be a Pentagon Sailing Member to register for this course. If you are not a member, please head over to https://www.pentagonsailing.org/newmember to start your membership.

  Show details
• ASA-104 Bareboat Cruising Certification

  • Start
    30 May 2025
  •  
    9:00 AM
  • End
    01 Jun 2025
  •  
    5:00 PM
  • Location
    Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
  • Spaces left
    0

  Join waitlist

  ASA 104 Bareboat Cruising Certification (a 3-day, 2-night sail)

  Boat:
  48' Schooner Adventurer

  Skipper:
  Duncan Hood

  This a unique opportunity to gain real sailing experience while earning ASA's 104 Bareboat Cruising certification. Experienced instructor, Duncan Hood, will teach this class on his 48' Schooner Adventurer. Adventurer is a 1984 fore & aft staysail schooner manufactured by Cherubini Yachts in Riverside New Jersey. Duncan has offered to host club members on his boat during this sail and provide ASA 104 training. This three-day, two-night trip will give you more than enough experience to demonstrate confidently all the required skills and knowledge covered by the ASA 104 course so that you can charter a boat.

  Your fee covers ASA certification. PSC no longer gets a discount from ASA for the textbook.  Purchase one online.  Food and drinks on board are the crew's responsibility. 

  Additional information on ASA 104:
  ASA 104, Bareboat Cruising Certification

  Prerequisites:
  ASA requires 101 and 103 certifications before taking the course and recommends a minimum of 80 on-the-water sailing hours.

  Locations:
  Start - Dock F, Slip 2 Port Annapolis, MD

  End - Port Annapolis, MD

  Itinerary: 
  Sail from Port Annapolis and return the next day.

  Notes:
  A maximum of 1 FVSM may be used for this sail. If you use an FVSM, select the applicable ASA 104 with the FVSM payment option. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing this pricing option. The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

  Questions:
  Email Bay Commodore

  PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM

  
  

  Show details
• Advanced Coastal Cruising 4-Day Sail, ASA 106

  • Start
    05 Jun 2025
  •  
    10:00 AM
  • End
    08 Jun 2025
  •  
    5:00 PM
  • Location
    Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
  • Spaces left
    5
  • Registered
    1 registrant

  Register

   

  Coastal Cruising 4-Day Training Sail 

  Boat Name: Adventurer (48' schooner)
  

  Slip: Dock F, Slip 2, Port Annapolis, 7074 Bembe Beach Road, Annapolis, MD 21403

  Skipper: Duncan Hood

  Purpose/Training: A 4-day long trip on the Chesapeake Bay.  This is a training sail designed for people want to achieve ASA 106 and be able to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length in coastal and inland waters, in any conditions.  People who wish to receive the ASA certification must have completed the prerequisite courses and time on the water prior to starting this sail.  There is a significant amount of planning required of students for this event.  Experienced instructor, Duncan Hood, will teach this class on his 48' Schooner Adventurer. Adventurer is a 1984 fore & aft staysail schooner manufactured by Cherubini Yachts in Riverside New Jersey.

  Check back soon for sail plan. Join waitlist if sail sells out. 

  Preference will be given to crew who are obtaining their first ASA 106 certification.

  Certifications:
  ASA 106 certification awarded upon successful completion of this sail and a written test. Pursuance of either certification is not a requirement of participating on this sail.

  Prerequisites for ASA 106: ASA 101, 103, 104, and 105.
  

  Locations:
  Start - Dock F, Slip 2 Port Annapolis, MD

  End - Port Annapolis, MD

  POC: Bay Commodore at baycommodore@pentagonsailing.org

  A maximum of 2 FVSMs may be used for this sail. If you are using an FVSM(s), select the applicable registration type with FVSM(s) option. Check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.  The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

  Registration cost includes charter fees, ASA 106 exam and certification fee. PSC no longer receives a discount on ASA textbooks.  Purchase one directly online.

  
  

  Show details
• Bay Day Sail #1

  • When
    07 Jun 2025
  •  
    9:00 AM - 5:00 PM
  • Location
    Waypoints Annapolis 222 Severn Avenue, Bldg. 15 MD 21403 Annapolis, Maryland
  • Spaces left
    5

  Register

  Bay Day Sail

  Boat Name: Jeanneau 51 - Recovery Room 2018

  Skipper: Pablo Destefanis

  Purpose/Training: Bay day sails are predominantly recreational. Day sails are designed to build experience and provide an enjoyable on-the-water experience. There is not a specific list of training objectives for this sail.

  POC: Bay Commodore

  One FVSM may be used for this sail. If you are using an FVSM, select the Bay Day Sail with FVSM payment option. Please check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.

  The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.
  

  Please consider joining the Bay Skipper Program

  Show details
• Bay Day Sail #2

  • When
    08 Jun 2025
  •  
    9:00 AM - 5:00 PM
  • Location
    Waypoints Annapolis 222 Severn Avenue, Bldg. 15 MD 21403 Annapolis, Maryland
  • Spaces left
    8

  Register

  Bay Day Sail

  Boat Name: Jeanneau 51 - Recovery Room 2018

  Skipper: Pablo Destefanis

  Purpose/Training: Bay day sails are predominantly recreational. Day sails are designed to build experience and provide an enjoyable on-the-water experience. There is not a specific list of training objectives for this sail.

  POC: Bay Commodore

  One FVSM may be used for this sail. If you are using an FVSM, select the Bay Day Sail with FVSM payment option. Please check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.

  The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.
  

  Please consider joining the Bay Skipper Program

  Show details
• Racing - Summer Regatta

  • When
    14 Jun 2025
  •  
    8:30 AM - 5:00 PM
  • Location
    Capital Cove Marina, Joint Base Anacostia–Bolling, District of Columbia

  The Summer Regatta is the racing squadron's second weekend event of the year.  Expect multiple races throughout the day. This event is open to members of the PSC Racing Squadron; racers, please remember to sign up on the Racing Sign-Up Sheet.
  

  For more information, contact the Racing Commodore at racing@pentagonsailing.org.

  Show details
• ASA 114 Cruising Catamaran

  • When
    14 Jun 2025
  •  
    9:00 AM - 5:00 PM
  • Location
    Waypoints Yacht Charters, 222 Severn Avenue, Bldg. 15, Annapolis MD 21403 Annapolis, Maryland
  • Spaces left
    9

  Register

  Bay Training Sail

  Boat Name: Fountaine Pajot Saona 47 Maestro - 3 + 1 cab. - Dark Star - 2019

  Skipper: Dave Kunselman

  Training/Purpose: This sail is open to all club members. It is not necessary to be pursuing the ASA 114 certification. However, many aspects of this sail are designed around the ASA 114 Cruising Catamaran curriculum. Day sailing only included. ASA 114 is an advanced cruising standard for individuals with cruising experience. The standard includes those skills unique to a 30-50 foot multihull.
  *Note: Club training will take priority. If a member pursuing ASA 114 joins the waitlist, they will be given the spot of someone on the sail socially, but no later than three weeks before the sail.

  Prerequisites for ASA 114: ASA 101, 103, and 104.

  Certifications:
  ASA - ASA 114 certification awarded upon successful completion of this sail and a written test.

  POC: Bay Commodore
  

  A maximum of 2 FVSMs may be used for this sail. If you are using an FVSM(s), select the applicable Overnight Sail with FVSM(s) payment option. Please check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.
  

  Show details
• ASA 114 Cruising Catamaran

  • When
    15 Jun 2025
  •  
    9:00 AM - 5:00 PM
  • Location
    Waypoints Yacht Charters, 222 Severn Avenue, Bldg. 15, Annapolis MD 21403 Annapolis, Maryland
  • Spaces left
    11

  Register

  Bay Training Sail

  Boat Name: Fountaine Pajot Saona 47 Maestro - 3 + 1 cab. - Dark Star - 2019

  Skipper: Dave Kunselman

  Training/Purpose: This sail is open to all club members. It is not necessary to be pursuing the ASA 114 certification. However, many aspects of this sail are designed around the ASA 114 Cruising Catamaran curriculum. Day sailing only included. ASA 114 is an advanced cruising standard for individuals with cruising experience. The standard includes those skills unique to a 30-50 foot multihull.
  *Note: Club training will take priority. If a member pursuing ASA 114 joins the waitlist, they will be given the spot of someone on the sail socially, but no later than three weeks before the sail.

  Prerequisites for ASA 114: ASA 101, 103, and 104.

  Certifications:
  ASA - ASA 114 certification awarded upon successful completion of this sail and a written test.

  POC: Bay Commodore
  

  A maximum of 2 FVSMs may be used for this sail. If you are using an FVSM(s), select the applicable Overnight Sail with FVSM(s) payment option. Please check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.
  

  Show details
• ASA 101/103 Combined #3 @ Phillips School - Contemporary Education & OTW JBAB

  • Start
    18 Jun 2025
  •  
  • End
    29 Jun 2025
  •  
  • Schedule
    6 sessions
  • Location
    Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
  • Spaces left
    12

  Register

  ASA 101/103 Combined #3 [June]

  Never sailed before, or has it been a while? This is the course that will get you started!

  Upon completing this combined course, you can skipper a sloop-rigged keelboat of approximately 20 to 30 feet in length by day in light to moderate winds (up to 20 knots) and sea conditions.  

  Full Details

  Classroom: Phillips School - Contemporary Education, Activity Room, 7010 Braddock Rd., Annandale, VA  22003

  • 101 Classroom June 18 (6:00 PM to 8:30 PM)
  • 103 Classroom June 26 (6:00 PM to 8:30 PM)

  On-the-Water Location: Capital Cove Marina @ Joint Base Anacostia-Bolling
  

  • 101 OTW - June 21 & 22 (8:30 AM to 4:30 PM)
  • 103 OTW - June 28 & 29 (8:30 AM to 4:30 PM

  PSC Members may use up to 2 FVSMs for this class. FVSMs are worth $25.00 each for this class. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing either of these pricing options.

  If you have questions - please get in touch with the Training Commodore at trainingcommodore@pentagonsailing.org.

  P.S. You must be a Pentagon Sailing Member to register for this course. If you are not a member, please head over to https://www.pentagonsailing.org/newmember to start your membership.

  Show details
• ASA-104 Bareboat Cruising Certification

  • Start
    20 Jun 2025
  •  
    9:00 AM
  • End
    22 Jun 2025
  •  
    5:00 PM
  • Location
    Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
  • Spaces left
    6

  Register

  ASA 104 Bareboat Cruising Certification (a 3-day, 2-night sail)

  Boat:
  48' Schooner Adventurer

  Skipper:
  Duncan Hood

  This a unique opportunity to gain real sailing experience while earning ASA's 104 Bareboat Cruising certification. Experienced instructor, Duncan Hood, will teach this class on his 48' Schooner Adventurer. Adventurer is a 1984 fore & aft staysail schooner manufactured by Cherubini Yachts in Riverside New Jersey. Duncan has offered to host club members on his boat during this sail and provide ASA 104 training. This three-day, two-night trip will give you more than enough experience to demonstrate confidently all the required skills and knowledge covered by the ASA 104 course so that you can charter a boat.

  Your fee covers ASA certification. PSC no longer gets a discount from ASA for the textbook.  Purchase one online.  Food and drinks on board are the crew's responsibility. 

  Additional information on ASA 104:
  ASA 104, Bareboat Cruising Certification

  Prerequisites:
  ASA requires 101 and 103 certifications before taking the course and recommends a minimum of 80 on-the-water sailing hours.

  Locations:
  Start - Dock F, Slip 2 Port Annapolis, MD

  End - Port Annapolis, MD

  Itinerary: 
  Sail from Port Annapolis and return the next day.

  Notes:
  A maximum of 1 FVSM may be used for this sail. If you use an FVSM, select the applicable ASA 104 with the FVSM payment option. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing this pricing option. The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

  Questions:
  Email Bay Commodore

  PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM

  
  

  Show details
• ASA 204 - IQC Instructor Training for Bareboat Cruising

  • Start
    27 Jun 2025
  •  
    9:00 AM
  • End
    29 Jun 2025
  •  
    5:00 PM
  • Location
    Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
  • Spaces left
    5

  Register

  ASA 204 - IQC Instructor Training for Bareboat Cruising

  Boat:
  48' Schooner Adventurer

  Skipper:
  Duncan Hood

  This a unique opportunity to gain real sailing experience while earning ASA's 204 Bareboat Cruising certification. Experienced instructor, Duncan Hood, will teach this class on his 48' Schooner Adventurer. Adventurer is a 1984 fore & aft staysail schooner manufactured by Cherubini Yachts in Riverside New Jersey. Duncan has offered to host club members on his boat during this sail and provide ASA 204 training. This two-day, one-night trip will give you more than enough experience to demonstrate confidently all the required skills and knowledge covered by the ASA 204 course so that you can charter a boat.

  Your fee covers ASA exam and certification. Food and drinks on board are the crew's responsibility. 

  Additional information on ASA 104:
  ASA 104, Bareboat Cruising Certification

  Prerequisites:
  ASA requires 104 certification before taking the course and recommends a minimum of 80 on-the-water sailing hours.

  Locations:
  Start - Dock F, Slip 2 Port Annapolis, MD

  End - Port Annapolis, MD

  Itinerary: 
  Sail from Port Annapolis and return to the same location.

  Notes:
  A maximum of 1 FVSM may be used for this sail. If you use an FVSM, select the applicable ASA 204 with the FVSM payment option. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing this pricing option. The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

  Questions:
  Email Bay Commodore

  PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM

  
  

  Show details
• Racing - Summer II Series

  • Start
    01 Jul 2025
  •  
  • End
    12 Aug 2025
  •  
  • Schedule
    7 sessions
  • Location
    Capital Cove Marina

  These races are part of DISC's Summer II Series.

  The event is open to members of the PSC Racing Squadron.  Racing Squadron members, remember to sign up on the Racing Sign-Up Sheet.

  For more information, contact the Racing Commodore at racing@pentagonsailing.org.

  Show details
• ASA 101/103 Combined #4 @ Phillips School - Contemporary Education & OTW JBAB

  • Start
    10 Jul 2025
  •  
  • End
    20 Jul 2025
  •  
  • Schedule
    6 sessions
  • Location
    Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
  • Spaces left
    10

  Register

  ASA 101/103 Combined #4 [July]

  Never sailed before, or has it been a while? This is the course that will get you started!

  Upon completing this combined course, you can skipper a sloop-rigged keelboat of approximately 20 to 30 feet in length by day in light to moderate winds (up to 20 knots) and sea conditions.  

  Full Details

  Classroom: Phillips School - Contemporary Education, Activity Room, 7010 Braddock Rd., Annandale, VA  22003

  • 101 Classroom July 10 (6:00 PM to 8:30 PM)
  • 103 Classroom July 17 (6:00 PM to 8:30 PM)

  On-the-Water Location: Capital Cove Marina @ Joint Base Anacostia-Bolling
  

  • 101 OTW - July 12 & 13 (8:30 AM to 4:30 PM)
  • 103 OTW - July 17 & 19 (8:30 AM to 4:30 PM

  PSC Members may use up to 2 FVSMs for this class. FVSMs are worth $25.00 each for this class. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing either of these pricing options.

  If you have questions - please get in touch with the Training Commodore at trainingcommodore@pentagonsailing.org.

  P.S. You must be a Pentagon Sailing Member to register for this course. If you are not a member, please head over to https://www.pentagonsailing.org/newmember to start your membership.

  Show details
• Racing - Fall Series

  • Start
    19 Aug 2025
  •  
  • End
    16 Sep 2025
  •  
  • Schedule
    5 sessions
  • Location
    Capital Cove Marina

  These races are part of DISC's Fall Series, and are open to members of the PSC Racing Squadron.  Racing Squadron members, remember to sign up on the Racing Sign-Up Sheet.

  The last race of the series will be followed by DISC's annual chili cook-off.

  For more information, contact the Racing Commodore at racing@pentagonsailing.org.

  Show details
• ASA-104 Bareboat Cruising Certification

  • Start
    22 Aug 2025
  •  
    9:00 AM
  • End
    24 Aug 2025
  •  
    5:00 PM
  • Location
    Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
  • Spaces left
    6

  Register

  ASA 104 Bareboat Cruising Certification (a 3-day, 2-night sail)

  Boat:
  48' Schooner Adventurer

  Skipper:
  Duncan Hood

  This a unique opportunity to gain real sailing experience while earning ASA's 104 Bareboat Cruising certification. Experienced instructor, Duncan Hood, will teach this class on his 48' Schooner Adventurer. Adventurer is a 1984 fore & aft staysail schooner manufactured by Cherubini Yachts in Riverside New Jersey. Duncan has offered to host club members on his boat during this sail and provide ASA 104 training. This three-day, two-night trip will give you more than enough experience to demonstrate confidently all the required skills and knowledge covered by the ASA 104 course so that you can charter a boat.

  Your fee covers ASA certification. PSC no longer gets a discount from ASA for the textbook.  Purchase one online.  Food and drinks on board are the crew's responsibility. 

  Additional information on ASA 104:
  ASA 104, Bareboat Cruising Certification

  Prerequisites:
  ASA requires 101 and 103 certifications before taking the course and recommends a minimum of 80 on-the-water sailing hours.

  Locations:
  Start - Dock F, Slip 2 Port Annapolis, MD

  End - Port Annapolis, MD

  Itinerary: 
  Sail from Port Annapolis and return the next day.

  Notes:
  A maximum of 1 FVSM may be used for this sail. If you use an FVSM, select the applicable ASA 104 with the FVSM payment option. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing this pricing option. The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

  Questions:
  Email Bay Commodore

  PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM

  
  

  Show details
• 2025 PSC Labor Day Raft-Up: Club-Chartered Catamaran

  • Start
    30 Aug 2025
  •  
    9:00 AM
  • End
    01 Sep 2025
  •  
    5:00 PM
  • Location
    Waypoints Annapolis, 222 Severn Avenue, Bldg. 15 MD 21403 Annapolis, Maryland
  • Spaces left
    8

  Register

  
  

  2024 PSC Labor Day Raft-Up: Club-Chartered 47' Catamaran

  • Location: Waypoints Annapolis, 222 Severn Ave, Annapolis, MD 21403 Google maps
  • • Parking space may be limited. Try to carpool.

  REGISTRATION

  • 2025 PSC Labor Day Raft-Up: Club-Chartered Boat (3-Day Bay Sail) – shared cabin, OR salon

  Miscellaneous costs (fuel, pump-out, dock fees, meals) not included.

  Boat: 47' Catamaran Fountaine Pajot Saona 47 Maestro - 3 + 1 cab. - Dark Star - 2019

  Skipper:  TBD 

  This is a multi-day social sail over the Labor Day weekend. We depart the marina on Saturday and meet other boats on the bay, raft-up, and spend the day on the water. 

  Theme: TBD

  Location: TBD

  This is a great multi-day experience, where you get to experience the liveaboard style, plus you get to raft-up with other boats. The sail is a great time to practice any skills you may need for a certification, or just to make sure you keep them sharp. If all you want is relax, there will be multiple fore-decks where you can do so.

  Monday we return to our home ports.

  We look forward to seeing you. Please pass the information about the Raft Up to anyone who wants to attend and let the skipper know if you have any questions.

  Registration price only covers charter costs. Additional costs such as food, pump-out, fuel, and slip fees will be shared by the crew.

  The charter boat is a catamaran with three 2-person cabins and three singles in salon (sleeping nine). You can check it out here.

  The fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

  POC: Bay Commodore Sumeet C.

  PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM

  Show details
• ASA-104 Bareboat Cruising Certification

  • Start
    05 Sep 2025
  •  
    9:00 AM
  • End
    07 Sep 2025
  •  
    5:00 PM
  • Location
    Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
  • Spaces left
    6

  Register

  ASA 104 Bareboat Cruising Certification (a 3-day, 2-night sail)

  Boat:
  48' Schooner Adventurer

  Skipper:
  Duncan Hood

  This a unique opportunity to gain real sailing experience while earning ASA's 104 Bareboat Cruising certification. Experienced instructor, Duncan Hood, will teach this class on his 48' Schooner Adventurer. Adventurer is a 1984 fore & aft staysail schooner manufactured by Cherubini Yachts in Riverside New Jersey. Duncan has offered to host club members on his boat during this sail and provide ASA 104 training. This three-day, two-night trip will give you more than enough experience to demonstrate confidently all the required skills and knowledge covered by the ASA 104 course so that you can charter a boat.

  Your fee covers ASA certification. PSC no longer gets a discount from ASA for the textbook.  Purchase one online.  Food and drinks on board are the crew's responsibility. 

  Additional information on ASA 104:
  ASA 104, Bareboat Cruising Certification

  Prerequisites:
  ASA requires 101 and 103 certifications before taking the course and recommends a minimum of 80 on-the-water sailing hours.

  Locations:
  Start - Dock F, Slip 2 Port Annapolis, MD

  End - Port Annapolis, MD

  Itinerary: 
  Sail from Port Annapolis and return the next day.

  Notes:
  A maximum of 1 FVSM may be used for this sail. If you use an FVSM, select the applicable ASA 104 with the FVSM payment option. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing this pricing option. The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

  Questions:
  Email Bay Commodore

  PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM

  
  

  Show details
• Advanced Coastal Cruising 4-Day Sail, ASA 106

  • Start
    11 Sep 2025
  •  
    10:00 AM
  • End
    14 Sep 2025
  •  
    5:00 PM
  • Location
    Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
  • Spaces left
    4
  • Registered
    2 registrants

  Register

   

  Coastal Cruising 4-Day Training Sail 

  Boat Name: Adventurer (48' schooner)
  

  Slip: Dock F, Slip 2, Port Annapolis, 7074 Bembe Beach Road, Annapolis, MD 21403

  Skipper: Duncan Hood

  Purpose/Training: A 4-day long trip on the Chesapeake Bay.  This is a training sail designed for people want to achieve ASA 106 and be able to safely act as skipper and crew of a sailing vessel about 30 to 50 feet in length in coastal and inland waters, in any conditions.  People who wish to receive the ASA certification must have completed the prerequisite courses and time on the water prior to starting this sail.  There is a significant amount of planning required of students for this event.  Experienced instructor, Duncan Hood, will teach this class on his 48' Schooner Adventurer. Adventurer is a 1984 fore & aft staysail schooner manufactured by Cherubini Yachts in Riverside New Jersey.

  Check back soon for sail plan. Join waitlist if sail sells out. 

  Preference will be given to crew who are obtaining their first ASA 106 certification.

  Certifications:
  ASA 106 certification awarded upon successful completion of this sail and a written test. Pursuance of either certification is not a requirement of participating on this sail.

  Prerequisites for ASA 106: ASA 101, 103, 104, and 105.
  

  Locations:
  Start - Dock F, Slip 2 Port Annapolis, MD

  End - Port Annapolis, MD

  POC: Bay Commodore at baycommodore@pentagonsailing.org

  A maximum of 2 FVSMs may be used for this sail. If you are using an FVSM(s), select the applicable registration type with FVSM(s) option. Check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.  The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

  Registration cost includes charter fees, ASA 106 exam and certification fee. PSC no longer receives a discount on ASA textbooks.  Purchase one directly online.

  
  

  Show details
• ASA 101/103 Combined #5 @ Phillips School - Contemporary Education & OTW JBAB

  • Start
    11 Sep 2025
  •  
  • End
    21 Sep 2025
  •  
  • Schedule
    6 sessions
  • Location
    Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
  • Spaces left
    9

  Register

  ASA 101/103 Combined #5 [September]

  Never sailed before, or has it been a while? This is the course that will get you started!

  Upon completing this combined course, you can skipper a sloop-rigged keelboat of approximately 20 to 30 feet in length by day in light to moderate winds (up to 20 knots) and sea conditions.  

  Full Details

  Classroom: Phillips School - Contemporary Education, Activity Room, 7010 Braddock Rd., Annandale, VA  22003

  • 101 Classroom Sept. 11 (6:00 PM to 8:30 PM)
  • 103 Classroom Sept. 18 (6:00 PM to 8:30 PM)

  On-the-Water Location: Capital Cove Marina @ Joint Base Anacostia-Bolling
  

  • 101 OTW - Sept. 11 & 14 (8:30 AM to 4:30 PM)
  • 103 OTW - Sept. 20 & 21 (8:30 AM to 4:30 PM

  PSC Members may use up to 2 FVSMs for this class. FVSMs are worth $25.00 each for this class. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing either of these pricing options.

  If you have questions - please get in touch with the Training Commodore at trainingcommodore@pentagonsailing.org.

  P.S. You must be a Pentagon Sailing Member to register for this course. If you are not a member, please head over to https://www.pentagonsailing.org/newmember to start your membership.

  Show details
• ASA 204 - IQC Instructor Training for Bareboat Cruising

  • Start
    19 Sep 2025
  •  
    9:00 AM
  • End
    21 Sep 2025
  •  
    5:00 PM
  • Location
    Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
  • Spaces left
    6

  Register

  ASA 204 - IQC Instructor Training for Bareboat Cruising

  Boat:
  48' Schooner Adventurer

  Skipper:
  Duncan Hood

  This a unique opportunity to gain real sailing experience while earning ASA's 204 Bareboat Cruising certification. Experienced instructor, Duncan Hood, will teach this class on his 48' Schooner Adventurer. Adventurer is a 1984 fore & aft staysail schooner manufactured by Cherubini Yachts in Riverside New Jersey. Duncan has offered to host club members on his boat during this sail and provide ASA 204 training. This two-day, one-night trip will give you more than enough experience to demonstrate confidently all the required skills and knowledge covered by the ASA 204 course so that you can charter a boat.

  Your fee covers ASA exam and certification. Food and drinks on board are the crew's responsibility. 

  Additional information on ASA 104:
  ASA 104, Bareboat Cruising Certification

  Prerequisites:
  ASA requires 104 certification before taking the course and recommends a minimum of 80 on-the-water sailing hours.

  Locations:
  Start - Dock F, Slip 2 Port Annapolis, MD

  End - Port Annapolis, MD

  Itinerary: 
  Sail from Port Annapolis and return to the same location.

  Notes:
  A maximum of 1 FVSM may be used for this sail. If you use an FVSM, select the applicable ASA 204 with the FVSM payment option. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing this pricing option. The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.

  Questions:
  Email Bay Commodore

  PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM

  
  

  Show details
• Racing - Fall High Point - Three Bridges

  • When
    27 Sep 2025
  •  
    8:30 AM - 5:00 PM
  • Location
    Capital Cove Marina

  This is a longer race, on either a two or three bridges course.  Expect to begin at N4 and race to the Wilson Bridge, South Capitol Street Bridge on the Anacostia River, and 14th Street Bridge on the Potomac branch.

  This event is open to members of the PSC Racing Squadron; racers, remember to sign up on the Racing Sign-Up Sheet.

  For more information, contact the Racing Commodore at racing@pentagonsailing.org.

  Show details
• ASA 206 - Advanced Coastal Cruising Instructor

  • Start
    02 Oct 2025
  • End
    05 Oct 2025
  • Location
    Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
  • Spaces left
    4
  • Registered
    2 registrants

  Register

  PSC offers ASA 106/206, Advanced Coastal Cruising course on Adventurer with Duncan Hood

  
  

  PSC will be offering an ASA 206 class on Duncan Hood's 48' Cherubini schooner, “Adventurer.” This will be a 4 day live-aboard class which, among other exercises, will include the following:

  
  

  •        Night time navigation without electronics

  •        Anchoring

  •        Live MOB rescue, swimmer and non-swimmer assisted

  •        Adverse weather preparation

  •        Menu planning & Meal preparation

  •        Docking in different marinas & configurations

  •        Piloting & plotting

  •        Electronic navigation with chartplotter, radar and autopilot

  •        Spinnaker (weather permitting)

  
  

  The purpose behind ASA 206 certification is to train students and give them experience sailing a vessel between 30 and 50 feet in length on coastal and inland waters in varied conditions. This is meant to include mechanical problems that may come up, adverse weather conditions, emergency situations, and a single night sail. In this instructor training course (206) we will attempt to address these four areas.

  All exercises are based on ASA 206 requirements as stated in the ASA logbook for that level.

  Attending ASA 206 instructors are expected to have completed ASA 204/205 (Bareboat chartering/Coastal navigation), hold valid USGC Captain's licenses (if receiving consideration/compensation for teaching), and to have held these ratings for one year or more.

  1 FVSM may be used for this course.  Please verify you have available FVSM before registering at this rate.

  The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.
  

  This is always a fun and challenging class. Join us!

  
  

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• ASA 101/103 Combined #6 @ Phillips School - Contemporary Education & OTW JBAB

  • Start
    09 Oct 2025
  •  
  • End
    19 Oct 2025
  •  
  • Schedule
    6 sessions
  • Location
    Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
  • Spaces left
    12

  Register

  ASA 101/103 Combined #6 [October]

  Never sailed before, or has it been a while? This is the course that will get you started!

  Upon completing this combined course, you can skipper a sloop-rigged keelboat of approximately 20 to 30 feet in length by day in light to moderate winds (up to 20 knots) and sea conditions.  

  Full Details

  Classroom: Phillips School - Contemporary Education, Activity Room, 7010 Braddock Rd., Annandale, VA  22003

  • 101 Classroom Oct. 9 (6:00 PM to 8:30 PM)
  • 103 Classroom Oct. 16 (6:00 PM to 8:30 PM)

  On-the-Water Location: Capital Cove Marina @ Joint Base Anacostia-Bolling
  

  • 101 OTW - Oct. 11 & 12 (8:30 AM to 4:30 PM)
  • 103 OTW - Oct. 18 & 19 (8:30 AM to 4:30 PM

  PSC Members may use up to 2 FVSMs for this class. FVSMs are worth $25.00 each for this class. Please check the FVSM spreadsheet to ensure you have FVSM(s) available before choosing either of these pricing options.

  If you have questions - please get in touch with the Training Commodore at trainingcommodore@pentagonsailing.org.

  P.S. You must be a Pentagon Sailing Member to register for this course. If you are not a member, please head over to https://www.pentagonsailing.org/newmember to start your membership.

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• Racing - Fall High Point - Mount Vernon

  • When
    11 Oct 2025
  •  
    8:30 AM - 5:00 PM
  • Location
    Capital Cove Marina, Joint Base Anacostia–Bolling, District of Columbia

  The Mount Vernon Chase is a pursuit-style race.  Each boat will be given an individual start time, based on PHRF.  Boats will be scored in the order in which they cross the finish line, rather than having times corrected afterwards.  This is a longer race, and it's a great opportunity to enjoy the fall colors and see some scenery further from our usual venue.

  This event is open to members of the PSC Racing Squadron; racers, remember to sign up on the Racing Sign-Up Sheet.  For more information, contact the Racing Commodore at racing@pentagonsailing.org.

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• ASA 206 - Advanced Coastal Cruising Instructor

  • Start
    23 Oct 2025
  •  
    9:00 AM
  • End
    26 Oct 2025
  •  
    5:00 PM
  • Location
    Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
  • Spaces left
    5
  • Registered
    1 registrant

  Register

  PSC offers ASA 106/206, Advanced Coastal Cruising course on Adventurer with Duncan Hood

  
  

  PSC will be offering an ASA 206 class on Duncan Hood's 48' Cherubini schooner, “Adventurer.” This will be a 4 day live-aboard class which, among other exercises, will include the following:

  
  

  •        Night time navigation without electronics

  •        Anchoring

  •        Live MOB rescue, swimmer and non-swimmer assisted

  •        Adverse weather preparation

  •        Menu planning & Meal preparation

  •        Docking in different marinas & configurations

  •        Piloting & plotting

  •        Electronic navigation with chartplotter, radar and autopilot

  •        Spinnaker (weather permitting)

  
  

  The purpose behind ASA 206 certification is to train students and give them experience sailing a vessel between 30 and 50 feet in length on coastal and inland waters in varied conditions. This is meant to include mechanical problems that may come up, adverse weather conditions, emergency situations, and a single night sail. In this instructor training course (206) we will attempt to address these four areas.

  All exercises are based on ASA 206 requirements as stated in the ASA logbook for that level.

  Attending ASA 206 instructors are expected to have completed ASA 204/205 (Bareboat chartering/Coastal navigation), hold valid USGC Captain's licenses (if receiving consideration/compensation for teaching), and to have held these ratings for one year or more.

  1 FVSM may be used for this course.  Please verify you have available FVSM before registering at this rate.

  The course fee will not be refunded if cancellation occurs within 30 days of the start date of the sail, unless the participant finds a replacement. The club will assist with this, but will not be responsible for finding a replacement.
  

  This is always a fun and challenging class. Join us!

  
  

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• Racing - Fall High Point - Frostbite Regatta

  • When
    25 Oct 2025
  •  
    8:30 AM - 5:00 PM
  • Location
    Capital Cove Marina

  The Frostbite Regatta is the third event of DISC’s Fall High Point Series.  It’s a single-day, multi-race event and is DISC’s last on-the-water event of the year.  

  This event is open to members of the PSC Racing Squadron; racers, remember to sign up on the Racing Sign-Up Sheet.

  For more information, contact the Racing Commodore at racing@pentagonsailing.org.

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• Hydrilla Cup

  • When
    01 Nov 2025
  •  
    9:00 AM - 4:00 PM
  • Location
    Capitol Cove Marina, Joint Base Anacostia-Bolling

  The Hydrilla Cup is a PSC social event hosted by the Racing Squadron. Join us for a day of races, fellowship, and a cookout!

  The main event will be a series of two to three races on the Potomac River in which teams of PSC members compete against each other to claim victory on one of our Capri 22's.  We'll follow the racing with a cookout at the marina.

  This event is free, but registration is required since there's limited space on the boats.  If you'd like to share a dish for the cookout, please send a note to racing@pentagonsailing.org.  If you'd like to attend the cookout but not sail, there's unlimited space to attend.

  Note:  This event is held on Joint Base Anacostia-Bolling; you must have an ID card (or a DIBDS card) that allows access to the base to participate.

  0900   Welcome, Intro to Racing, prepare boats
  1000   Launch boats, warm up
  1100   Start time for first race
  1430   Estimated finish time for last race
  1500   Cookout and awards

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• Racing - DISC Awards Party

  • When
    02 Dec 2025
  •  
    6:00 PM - 8:30 PM
  • Location
    Murphy's Grand Irish Pub, 713 King St, Alexandria, Virginia

  Finish the year's racing season with the DISC Awards Ceremony!  Enjoy Murphy's delicious buffet and each other's company as we collect a few trophies from a year of hard competition!

  The event is open to members of the PSC Racing Squadron and a guest.  Remember to sign up on the Racing Sign-Up Sheet to let the team know you'll be there.

  For more information, contact the Racing Commodore at racing@pentagonsailing.org.

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