Bay Sail Schedule

Switch to Calendar View

• ASA 214 IQC Cruising Catamaran

  • When
    05 May 2026
  •  
    9:00 AM - 5:00 PM
  • Location
    Sail Solomon Sail Solomon, Spring Cove Marina, 455 Lore Road, Solomons MD 20688
  • Spaces left
    0

  Bay Training Sail

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

  Skipper: Duncan Hood

  Training/Purpose: The ASA 214 IQC certifies a candidate for teaching ASA 114, Cruising Catamaran course. Certification requires the Instructor Candidate to pass written examinations and on-the-water skill evaluation. 

  Prerequisites ASA 204

  Certifications:
  ASA - ASA 214 certification awarded upon successful completion of this sail and a written test.

  POC: Bay Commodore

  Show details
• Close Quarter Maneuvering (ASA 118)

  • When
    16 May 2026
  •  
    9:00 AM - 5:00 PM
  • Location
    Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
  • Spaces left
    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)

  • When
    17 May 2026
  •  
    9:00 AM - 5:00 PM
  • Location
    Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
  • Spaces left
    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

  • 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 left
    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

  • 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 left
    1

  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

  • 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 left
    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

  • Start
    30 May 2026
  •  
    9:00 AM
  • End
    31 May 2026
  •  
    4:00 PM
  • Location
    Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
  • Spaces left
    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

  • When
    01 Jun 2026
  •  
    9:00 AM - 4:00 PM
  • Location
    Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
  • Spaces left
    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

  • Start
    05 Jun 2026
  •  
    9:00 AM
  • End
    07 Jun 2026
  •  
    5:00 PM
  • Location
    Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
  • Spaces left
    0

  Join waitlist

  ASA 104 Bareboat Cruising 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
• Bay Overnight 2-Day Sail #2

  • Start
    06 Jun 2026
  •  
    9:00 AM
  • End
    07 Jun 2026
  •  
    4:00 PM
  • Location
    Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
  • Spaces left
    3

  Register

  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:  Matt Tobias

  POC: Bay Commodore at baycommodore@pentagonsailing.org

  Please consider joining the Bay Skipper Program

  Show details
• Bay Night Sail #1

  • Start
    20 Jun 2026
  •  
    9:00 AM
  • End
    21 Jun 2026
  •  
    4:00 PM
  • Location
    Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
  • Spaces left
    5

  Register

  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:  Bill Diehl

  Prerequisite: ASA 104

  POC: Bay Commodore at baycommodore@pentagonsailing.org

  Please consider joining the Bay Skipper Program

  Show details
• Bay Day Sail #2

  • When
    22 Jun 2026
  •  
    9:00 AM - 4:00 PM
  • Location
    Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688
  • Spaces left
    4

  Register

  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:  Justin Riordan

  POC: Bay Commodore at baycommodore@pentagonsailing.org

  Please consider joining the Bay Skipper Program

  Show details
• ASA 106/206 - Offshore Cruising/Instructor Training

  • Start
    27 Jun 2026
  •  
    9:00 AM
  • End
    30 Jun 2026
  •  
    5:00 PM
  • Location
    Port Annapolis, Dock F, Slip 2, 7074 Bembe Beach Rd, Annapolis, MD 21403
  • Spaces left
    3

  Register

  ASA 106 Offshore Cruising or 206 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 106 Offshore Cruising certification or ASA 206 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 106 or 206 training. This four-day, three-night trip will give you more than enough experience to demonstrate confidently all the required skills and knowledge covered by the ASA 106/206 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 106:ASA 106, Offshore Cruising Certification

  Prerequisites:
  For 206 ASA requires 106 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 106/206 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