Bay Sail Schedule

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• ASA 104/204 - Bareboat Cruising/Instructor Training

  • Start
    11 Sep 2026
  •  
    9:00 AM
  • End
    13 Sep 2026
  •  
    5:00 PM
  • Location
    Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
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  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 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 104/204 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

  
  

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• Bay Day Sail #3

  • When
    11 Sep 2026
  •  
    9:00 AM - 4:00 PM
  • Location
    Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
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  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:  Jonah Brewer

  POC: Bay Commodore at baycommodore@pentagonsailing.org

  Please consider joining the Bay Skipper Program

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• Bay Night Sail #2

  • Start
    12 Sep 2026
  •  
    9:00 AM
  • End
    13 Sep 2026
  •  
    4:00 PM
  • Location
    Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
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  Bay 2-Day Sail

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

  Overnight 2-Day sail with sailing at night from Sail Solomons on the Chesapeake Bay.  Sail first day, sail at night on the Chesapeake, then sail second day and return to port.  A social sail for those who just want to spend time on the water, get experience sailing at night and can also be used for qualifications for those in the PSC Bay Skipper Program.

  Boat: Serenity, Jeanneau Sun Odyssey 379

  Skipper:  Jonah Brewer

  POC: Bay Commodore at baycommodore@pentagonsailing.org

  Please consider joining the Bay Skipper Program

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• Bay Night Sail #3

  • Start
    18 Sep 2026
  •  
    9:00 AM
  • End
    19 Sep 2026
  •  
    4:00 PM
  • Location
    Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
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    0

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  Bay Night Sail

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

  This is a 2-Day Night sail from Sail Solomons on the Chesapeake Bay.  Sail first day, sail into the night in watches, then sail second day and return to port.  An intense sail where you will gain experience sailing at night.  This also qualifies for those in the PSC Bay Skipper Program.

  Boat: Jeanneau 379 Serenity

  Skipper:  Raul Cardenal

  Prerequisite: ASA 103

  POC: Bay Commodore at baycommodore@pentagonsailing.org

  Please consider joining the Bay Skipper Program

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• ASA 114 Cruising Catamaran

  • Start
    19 Sep 2026
  •  
    9:00 AM
  • End
    20 Sep 2026
  •  
    5:00 PM
  • Location
    Sail Solomon Sail Solomon, Spring Cove Marina, 455 Lore Road, Solomons MD 20688
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  Bay Training Sail

  Boat Name: SV Second Site, 2023 Seawind 1260 Catamaran.

  Skipper: Jonah Brewer, Bill Schwab

  Training/Purpose: The ASA 114 certifies a candidate for Cruising Catamaran.

  ASA 114 is an advanced sailing certification for individuals who want to skipper or crew a 30–50 foot cruising multihull (catamaran) in coastal waters. It builds on prior ASA standards (typically 101, 103, and 104) and focuses on the unique handling, safety, and performance characteristics of multihulls. You’ll practice essential sailing maneuvers under both sail and power, including handling twin engines, navigating tight spaces, and performing man-overboard recoveries.

  Learn more about ASA 114 and order your text book through the ASA Website.

  Prerequisites ASA 101, 103, 104.

  POC: Bay Commodore

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• Bay Social Sail on Schooner Adventurer

  • Start
    26 Sep 2026
  •  
    9:00 AM
  • End
    27 Sep 2026
  •  
    5:00 PM
  • Location
    Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
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  Bay Social Sail with Duncan Hood

  Boat: 48' Schooner Adventurer

  Skipper: Duncan Hood

  This is a unique opportunity to join other PSC members on an incredible schooner sailing experience on the Chesapeake Bay. Adventurer is a 1984 fore & aft staysail schooner manufactured by Cherubini Yachts in Riverside New Jersey. This two-day, one-night trip will be a great time for all and provide members the experience to crew this unique sailing vessel.

  Your registration fee is for the boat charter. Food and drinks on board will be coordinated and purchased by the crew.

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

  Overnight: Anchor or Dock (location tbd)

  End - Port Annapolis, MD

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

  Notes:
  The sail 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

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• Bay 2-Day Sail #5 (no night sailing)

  • Start
    03 Oct 2026
  •  
    9:00 AM
  • End
    04 Oct 2026
  •  
    4:00 PM
  • Location
    Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
  • Spaces left
    0

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  Bay 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: Moxie, Jeanneau 39i

  Skipper:  Bill Diehl

  POC: Bay Commodore at baycommodore@pentagonsailing.org

  Please consider joining the Bay Skipper Program

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