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All PSC events are listed below.  To view only Racing or Wednesday Social Sail events, use the drop down menus under the Events tab.  To view Events as a Calendar, use the "Switch to Calendar View" link.

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Club Activities

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

    • 24 Jan 2025
    • 08 Aug 2025
    • 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!

    Show details

  • River Boat Rental - 2025 Season

    • 12 Mar 2025
    • 25 Oct 2025
    • Capital Cove Marina, JBAB
    • 100

    PSC River Boat Rental - 2025 Season

    Aguila, Peregrine, Merlin. and Osprey are available for rental on Monday, Thursday, Saturday and Sunday when the boats are not being used by Racing, Social, and Training. Check boat availability and reserve your boat at the following google sheet,

    PSC River Sailboat Availablity

    Complete this registration then go back to the google sheet and record the date that the reservation was paid for.

    The skipper of the boat must have an ASA 101/103 or USNSA B-KBS (or higher) certification AND have successfully completed a NASBLA approved Boating Safety Course. Boating safety card must be carried by the skipper at all times when sailing on the Potomac River. Please also refer to the River Boat Policies.

    Efforts have been made to reflect restricted periods in the scheduling app such as ASA sailing classes, social sailing dates, racing, and scheduled maintenance, however, unscheduled or unforeseen maintenance may result in the unavailability of a boat even after confirmation of its use.

    Rental Periods:

    • 4hrs. Morning  8:00 AM  - 2:00 PM
    • 4hrs  Afternoon 2:00 PM - Sunset

    PSC Members The price for a 4-hour rental is $50. If you have volunteered, up to two FVSMs at $25 per FVSM may be used to defer the cost of the boat rental. The rental periods are 4hrs. From 8 am to 2 pm and 4hrs. From 2 pm to sunset. You may reserve the boat for 8hrs. by booking both the morning and afternoon rental periods on the same day. Please check the FVSM spreadsheet to make sure you have FVSM(s) available before choosing either of these pricing options.

    Prior to departure, you must complete a Departure River Float Plan
    Upon return to the slip,  complete a Return River Float Plan

    For any reservation questions, contact John Spahn jespahn1@aol.com

    The boats are located at Capital Cove Marina JBAB, in slips:

    34- Aguila (combo "2000")

    35 - Peregrine (combo "4000")

    The club house lock combo is "7721" you will need this combo to get PFD's and the boat log books.

    Prior to departure, please complete a Departure River Float Plan

    Upon return to the slip, please complete Return River Float Plan

    All River Boat use must comply with the Club's River Boat Policies and the PFD Policies:[https://www.pentagonsailing.org/River-Boat-Policies] and [https://www.pentagonsailing.org/PFD]

    Please review these policies before taking a boat out.

    Be sure to review the wind and weather conditions prior to your planned sail to confirm suitability for sailing in accordance with PSC policy. If the weather is not cooperating, contact John Spahn @ jespahn1@aol.com to reschedule your sail.
    Show details

  • Winter Training: Rules of the Road

    • 15 Mar 2025
    • 05 Apr 2025
    • 2 sessions
    • Phillips School For Contemporary Education, 7010 Braddock Rd, Annandale, VA 22003
    • 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!

    Show details

  • Racing - DISC Skippers and Crew Meeting

    • 01 Apr 2025
    • 6:00 PM - 8:30 PM
    • 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

    • 07 Apr 2025
    • 28 Apr 2025
    • 4 sessions
    • 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

    • 08 Apr 2025
    • 06 May 2025
    • 5 sessions
    • 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

    • 13 Apr 2025
    • 2:00 PM - 6:00 PM
    • Murphy's Grand Irish Pub
    • 43
    Register
    Show details

  • Advanced Coastal Cruising 4-Day Sail, ASA 106

    • 24 Apr 2025
    • 10:00 AM
    • 27 Apr 2025
    • 5:00 PM
    • Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
    • 4
    • 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 #1 @ Phillips School - Contemporary Education & OTW JBAB

    • 24 Apr 2025
    • 04 May 2025
    • 6 sessions
    • Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
    • 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-104 Bareboat Cruising Certification

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

    • 10 May 2025
    • 8:30 AM - 5:00 PM
    • 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.

    Show details

  • Racing - Summer I Series

    • 13 May 2025
    • 24 Jun 2025
    • 7 sessions
    • 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)

    • 17 May 2025
    • 9:00 AM - 5:00 PM
    • Waypoints Annapolis, 222 Severn Ave, Annapolis, MD 21403
    • 3
    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)

    • 18 May 2025
    • 9:00 AM - 5:00 PM
    • Waypoints Annapolis, 222 Severn Ave, Annapolis, MD 21403
    • 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

    • 24 May 2025
    • 9:00 AM
    • 26 May 2025
    • 5:00 PM
    • Waypoints Annapolis, 222 Severn Avenue, Bldg. 15 MD 21403 Annapolis, Maryland
    • 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

    • 29 May 2025
    • 08 Jun 2025
    • 6 sessions
    • Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
    • 4
    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

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

    • 05 Jun 2025
    • 10:00 AM
    • 08 Jun 2025
    • 5:00 PM
    • Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
    • 5
    • 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

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

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

    • 14 Jun 2025
    • 8:30 AM - 5:00 PM
    • 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

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

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

    • 18 Jun 2025
    • 29 Jun 2025
    • 6 sessions
    • Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
    • 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

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

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

  • ASA 204 - IQC Instructor Training for Bareboat Cruising

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

    • 01 Jul 2025
    • 12 Aug 2025
    • 7 sessions
    • 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

    • 10 Jul 2025
    • 20 Jul 2025
    • 6 sessions
    • Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
    • 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

    • 19 Aug 2025
    • 16 Sep 2025
    • 5 sessions
    • 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

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

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

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

    • 11 Sep 2025
    • 10:00 AM
    • 14 Sep 2025
    • 5:00 PM
    • Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
    • 4
    • 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

    • 11 Sep 2025
    • 21 Sep 2025
    • 6 sessions
    • Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
    • 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

  • Racing - Fall High Point - Three Bridges

    • 27 Sep 2025
    • 8:30 AM - 5:00 PM
    • 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

    • 02 Oct 2025
    • 05 Oct 2025
    • Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
    • 4
    • 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!


    Show details

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

    • 09 Oct 2025
    • 19 Oct 2025
    • 6 sessions
    • Phillips School - Contemporary Education, Annandale, VA & On the Water JBAB
    • 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.

    Show details

  • Racing - Fall High Point - Mount Vernon

    • 11 Oct 2025
    • 8:30 AM - 5:00 PM
    • 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.

    Show details

  • ASA 206 - Advanced Coastal Cruising Instructor

    • 23 Oct 2025
    • 9:00 AM
    • 26 Oct 2025
    • 5:00 PM
    • Dock F, Slip 2, Port Annapolis Marina, 7080 Bembe Beach Rd., Annapolis, MD 21403
    • 5
    • 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

    • 25 Oct 2025
    • 8:30 AM - 5:00 PM
    • 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

    • 01 Nov 2025
    • 9:00 AM - 4:00 PM
    • 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

    • 02 Dec 2025
    • 6:00 PM - 8:30 PM
    • 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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