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  • 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

  • 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
    • 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

  • Close Quarter Maneuvering (ASA 118)

    • 17 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

  • 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

  • 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
    • 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

    • 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

  • 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
    • 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

  • 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

  • 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

  • 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


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  • 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.
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  • 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.

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  • ASA 204 - IQC Instructor Training for Bareboat Cruising

    • 19 Sep 2025
    • 9:00 AM
    • 21 Sep 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


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  • 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.

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