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Bay Commodore

Bay Sails

The PSC offers members the opportunity to sail on the Chesapeake Bay with access to ASA training and social sails.  Members can progress with their sailing skills and enjoy sailing on larger boats on the Bay.

We also offer our annual Memorial Day and Labor Day raft-ups, from Friday, to Monday on the holiday weekends.  Raft-ups are open for members to invite guests on chartered boats as we gather with PSC boat owner members in a variety of beautiful locations on the Bay.

All Bay events will be listed on this page with new events posted as the season progresses. If you have any questions, please reach out to the Bay Commodore.

We look forward to seeing you on the Bay. 

Bay Sail Schedule

  • Close Quarter Maneuvering (ASA 118)

    • 16 May 2026
    • 9:00 AM - 5:00 PM
    • Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
    • 0
    Join waitlist

    BAY TRAINING DAY SAIL - CLOSE QUARTER MANEUVERING (CQM)

    Boat Name: Beneteau 323 Allora

    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

    Location:  Sail Solomons

    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.

    An ASA-118 textbook will be provided with this registration.

    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.

    Show details

  • Close Quarter Maneuvering (ASA 118)

    • 17 May 2026
    • 9:00 AM - 5:00 PM
    • Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
    • 0
    Join waitlist

    BAY TRAINING DAY SAIL - CLOSE QUARTER MANEUVERING (CQM)

    Boat Name: Beneteau 323 Allora

    Skipper: Jonah Brewer

    Purpose/Training: This class focuses on instructing 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 104

    Certifications:
    ASA - ASA 118 (Docking) certification awarded upon successful completion of CQM Session and a written test.

    Location: Sail Solomons

    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.

    An ASA-118 textbook will be provided with this registration.

    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.

    Show details

  • 2026 PSC Memorial Day Raft-Up: Club-Chartered Catamaran

    • 23 May 2026
    • 9:00 AM
    • 25 May 2026
    • 5:00 PM
    • Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
    • 0
    Join waitlist


    2026 PSC Memorial Day Raft-Up: Club-Chartered 41' Catamaran

    • Location: 

      Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688

      • Parking space may be limited. Try to carpool.


    REGISTRATION

    • 2026 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:  Second Sight 2023 41' Seawind 1260 Catamaran

    Skipper: Ross Rosiak   

    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:  Mardi Gras

    • 24 May 2025 - Raft Up  
    • 25 May 2025 - In port catered dinner 

    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: baycommodore@pentagonsailing.org

    Show details

  • 2026 PSC Memorial Day Raft-Up: Club-Chartered Boat #2

    • 23 May 2026
    • 9:00 AM
    • 25 May 2026
    • 5:00 PM
    • Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
    • 2
    Register

    2026 PSC Memorial Day Raft-Up: Club-Chartered Boat

    • Start: 23 May 2026, 9:00 AM
    • End: 25 May 2026, 5:00 PM
    • Location Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
    • Spaces available: 4

    REGISTRATION

    • 2026 PSC Memorial Day Raft-Up: Club-Chartered Boat (3-Day Bay Sail) – $475.00

    Includes one place in a shared cabin. Miscellaneous costs (fuel, pump-out, dock fees, meals) not included.

    2026 PSC Memorial Day Raft-Up: Club-Chartered Boat (3-Day Bay Sail) with 1 FVSM – $450.00

    Includes one place in a shared cabin. Miscellaneous costs (fuel, pump-out, dock fees, meals) not included.

    2026 PSC Memorial Day Raft-Up: Club-Chartered Boat #2

    Boat: Jeanneau 379 Serenity

    Skipper:  Jonah Brewer

    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.

    Location: San Domingo Creek

    The first night we anchor and then reconnect with the other boats. On the second night (Sunday), we dock in a marina (Oxford Safe Harbor) and have dinner at local restaurant (Capsize OXMD).

    Monday we return to our home ports.

    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.

    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 monohull with three 2-person cabins in salon (sleeping six). You can check it out here.

    Location: Sail Solomons 245 C St POB 441, Solomons, MD 20688

    POC: baycommodore@pentagonsailing.org

    Show details

  • 2026 PSC Memorial Day Raft-Up: Club-Chartered Boat #3

    • 23 May 2026
    • 9:00 AM
    • 25 May 2026
    • 5:00 PM
    • Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
    • 0
    Join waitlist

    2026 PSC Memorial Day Raft-Up: Club-Chartered Boat

    • Start 23 May 2026, 9:00 AM
    • End, 25 May 2026, 5:00 PM
    • Location Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
    • Spaces available 6

    REGISTRATION

    • 2026 PSC Memorial Day Raft-Up: Club-Chartered Boat (3-Day Bay Sail) – $475.00

    Includes one place in a shared cabin. Miscellaneous costs (fuel, pump-out, dock fees, meals) not included.

    2026 PSC Memorial Day Raft-Up: Club-Chartered Boat (3-Day Bay Sail) with 1 FVSM – $450.00

    Includes one place in a shared cabin. Miscellaneous costs (fuel, pump-out, dock fees, meals) not included.

    2026 PSC Memorial Day Raft-Up: Club-Chartered Boat #3

    Boat: Jeanneau 39i Moxie

    Skipper:  Matt Tobias

    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.

    Location: Sail Solomons

    The first night we anchor at San Domingo Creek and then reconnect with the other boats. On the second night (Sunday), we dock in a marina (Oxford Safe Harbor) and have dinner at local restaurant (Capsize OXND), get take out, or prepare meals on the boats (at each crew's preference).

    Monday we return to our home ports.

    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.

    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 monohull with three 2-person cabins in salon (sleeping six). You can check it out here.

    Location: Sail Solomons 245 C St POB 441, Solomons, MD 20688

    POC: baycommodore@pentagonsailing.org

    Show details

  • Bay Overnight 2-Day Sail #1

    • 30 May 2026
    • 9:00 AM
    • 31 May 2026
    • 4:00 PM
    • Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
    • 0
    Join waitlist

    Bay Overnight 2-Day Sail

    Location: Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688

    Overnight 2-Day sail from Sail Solomons on the Chesapeake Bay.  Sail first day, dock or anchor out at night (TBD), then sail second day and return to port.  A social sail for those who just want to spend time on the water but can also be used for qualifications for those in the PSC Bay Skipper Program.

    Boat: Jeanneau 379 Serenity

    Skipper:  Raul Cardenal

    POC: Bay Commodore at baycommodore@pentagonsailing.org

    Please consider joining the Bay Skipper Program

    Show details

  • Bay Day Sail #1

    • 01 Jun 2026
    • 9:00 AM - 4:00 PM
    • Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
    • 0
    Join waitlist

    Bay Day Sail

    Location: Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688

    Day sail from Solomons in Chesapeake Bay. A social sail for those who just want to spend time on the water but can also be used for qualifications for those in the PSC Bay Skipper Program.

    Boat: Jeanneau 379 Serenity

    Skipper:  Bill Diehl

    POC: Bay Commodore at baycommodore@pentagonsailing.org

    Please consider joining the Bay Skipper Program

    Show details

  • ASA 104/204 - Bareboat Cruising/Instructor Training

    • 05 Jun 2026
    • 9:00 AM
    • 07 Jun 2026
    • 5:00 PM
    • Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
    • 0
    Join waitlist

    ASA 104 Bareboat Cruising or 204 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 104 Bareboat Cruising certification or ASA 204 Instructor Qualification. 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 or 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 104/204 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:
    For 204 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 104/204 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

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