Pentagon Sailing Club upcoming events

Close Quarter Maneuvering (ASA 118) (16 May 2026)

Sat, 16 May 2026 13:00:00 GMT

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

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.

Participants are encouraged to join the Bay Skipper Program

Close Quarter Maneuvering (ASA 118) (17 May 2026)

Sun, 17 May 2026 13:00:00 GMT

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.

POC: baycommodore@pentagonsailing.org

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

Participants are encouraged to join the Bay Skipper Program

2026 PSC Memorial Day Raft-Up: Club-Chartered Catamaran (23 May 2026)

Sat, 23 May 2026 13:00:00 GMT

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: TBD

Location: TBD

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

PARTICIPANTS ARE ENCOURAGED TO JOIN THE BAY SKIPPER PROGRAM

2026 PSC Memorial Day Raft-Up: Club-Chartered Boat #2 (23 May 2026)

Sat, 23 May 2026 13:00:00 GMT

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

Start

23 May 2026

· 9:00 AM

25 May 2026

· 5:00 PM

Location

Sail Solomons Spring Cove Marina 455 Lore Road Solomons MD 20688

Spaces available

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: TBD

The first night we anchor and then reconnect with the other boats. On the second night (Sunday), we dock in a marina (location TBD) and have dinner at local restaurant (TBA), get take out, or prepare meals on the boats (at each crew's preference).

Monday we return to our home ports.

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

Bay Overnight 2-Day Sail #1 (30 May 2026)

Sat, 30 May 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 Solomons in 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: TBD

POC: Bay Commodore at baycommodore@pentagonsailing.org

Please consider joining the Bay Skipper Program

Bay Day Sail #1 (01 Jun 2026)

Mon, 01 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: TBD

POC: Bay Commodore at baycommodore@pentagonsailing.org

Please consider joining the Bay Skipper Program

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