Pentagon Sailing Club upcoming events

ASA 104/204 - Bareboat Cruising/Instructor Training (05 Jun 2026)

Fri, 05 Jun 2026 13:00:00 GMT

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

Bay Overnight 2-Day Sail #2 (06 Jun 2026)

Sat, 06 Jun 2026 13:00:00 GMT

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

ASA 114 Cruising Catamaran (13 Jun 2026)

Sat, 13 Jun 2026 13:00:00 GMT

Bay Training Sail

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

Skipper: Joanne and John Spahn

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

Bay Night Sail #1 (20 Jun 2026)

Sat, 20 Jun 2026 13:00:00 GMT

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 103

POC: Bay Commodore at baycommodore@pentagonsailing.org

Please consider joining the Bay Skipper Program

Bay Day Sail #2 (22 Jun 2026)

Mon, 22 Jun 2026 13:00:00 GMT

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

Bay Social Sail on Schooner Adventurer (22 Jun 2026)

Mon, 22 Jun 2026 13:00:00 GMT

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

WoW Bay Social Sail on Schooner Adventurer (24 Jun 2026)

Wed, 24 Jun 2026 13:00:00 GMT

WoW Bay Social Sail with Duncan Hood

Boat: 48' Schooner Adventurer

Skipper: Duncan Hood

This is a unique opportunity to join other WoW 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.

Questions:
Email Bay Commodore

ASA 106/206 - Offshore Cruising/Instructor Training (27 Jun 2026)

Sat, 27 Jun 2026 13:00:00 GMT

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

ASA 104 - Bareboat Cruising Training (10 Jul 2026)

Fri, 10 Jul 2026 13:00:00 GMT

ASA 104 Bareboat Cruising Training

Boat: Moxie. 2007 Jeanneau 39i

Skipper: Bill Diehl

This an opportunity to gain real sailing experience on the Bay while earning ASA's 104 Bareboat Cruising certification. This two-day, one-night trip will give you 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 exam and certification. Food and drinks on board are the crew's responsibility.

For additional information and to purchase your textbook go to the ASA 104 website: ASA 104 Bareboat Cruising Certification

Prerequisites: ASA 101 and ASA 103

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

Itinerary:
Sail from Sail Solomons 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 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

Bay 2-Day Sail #3 (No night sailing) (18 Jul 2026)

Sat, 18 Jul 2026 13:00:00 GMT

Bay 2-Day Sail

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

Boat: Windhover, Jeanneau 39i

Skipper: Pat Moran

POC: Bay Commodore at baycommodore@pentagonsailing.org

Please consider joining the Bay Skipper Program

WoW Bay Catamaran Overnight 2-Day Sail (25 Jul 2026)

Sat, 25 Jul 2026 13:00:00 GMT

Bay Overnight 2-Day Sail with Women on Water

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

This event is specifically for WoW members who would like to join out overnight 2-Day sail on a catamaran 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. There are three cabins and you will share one with another WoW sailor. This is a social sail for Women on Water to gain experience sailing on the Bay while enjoying time together.

Boat: Second Sight, Seawind 1260 Catamaran

Skippers: Joanne Spahn, Sue Neimeth

POC: Bay Commodore at baycommodore@pentagonsailing.org

Please consider joining the Bay Skipper Program

ASA 104 - Bareboat Cruising Training (16 Aug 2026)

Sun, 16 Aug 2026 13:00:00 GMT

ASA 104 Bareboat Cruising Training

Boat: Moxie. 2007 Jeanneau 39i

Skipper: Matt Tobias

Your fee covers ASA exam and certification. Food and drinks on board are the crew's responsibility.

For additional information and to purchase your textbook go to the ASA 104 website: ASA 104 Bareboat Cruising Certification

Prerequisites: ASA 101 and ASA 103

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

Itinerary:
Sail from Sail Solomons and return to the same location.

Questions:
Email Bay Commodore

2026 PSC Labor Day Raft-Up: Club-Chartered Catamaran (05 Sep 2026)

Sat, 05 Sep 2026 13:00:00 GMT

2026 PSC Labor 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 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: Second Sight 2023 41' Seawind 1260 Catamaran

Skipper: Ross Rosiak

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: Island Paradise

5 Sept 2025 - Raft Up on Patuxent River - location tbd
6 Sept 2025 - In port catered dinner at Spring Cover Marina

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. You can invite adult guests to join you, no minors. Please 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

2026 PSC Labor Day Raft-Up: Club-Chartered Boat Monohull (05 Sep 2026)

Sat, 05 Sep 2026 13:00:00 GMT

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

Start: 5 Sept 2026, 9:00 AM

End: 7 Sept 2026, 5:00 PM

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

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 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.

Location: Spring Cover Marina, Solomons Island

The first night (Saturday) we raft-up on the Patuxant (location tbd) and reconnect with the other boats. On the second night (Sunday), we dock at Spring Cover marina and have a catered dinner. On Monday we sail on the Chesapeake.

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

2026 PSC Labor Day Raft-Up: Club-Chartered Boat WoW (05 Sep 2026)

Sat, 05 Sep 2026 13:00:00 GMT

2026 PSC Labor Day Raft-Up: Club-Chartered WoW Boat

Start 5 Sept 2026, 9:00 AM

End, 7 Sept 2026, 5:00 PM

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

Spaces available 6

REGISTRATION

2026 PSC Labor 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 Labor 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 Labor Day Raft-Up: Club-Chartered WoW Boat

Boat: Jeanneau 39i Moxie

Skipper: Bri Foster

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.

Location: Sail Solomons

The first night we raft-up on the Putuxant River (location TBD) and reconnect with the other boats. On the second night (Sunday), we dock in a marina (Spring Cover Marina) and have a catered dinner. Monday we sail the Chesapeake.

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

ASA 104/204 - Bareboat Cruising/Instructor Training (11 Sep 2026)

Fri, 11 Sep 2026 13:00:00 GMT

ASA 104 Bareboat Cruising or 204 Instructor Training for Bareboat Cruising

Boat:48' Schooner Adventurer

Skipper:
Duncan Hood

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.

Questions:
Email Bay Commodore

Bay Day Sail #3 (11 Sep 2026)

Fri, 11 Sep 2026 13:00:00 GMT

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