Pentagon Sailing Club upcoming events

Bay Social Sail on Schooner Adventurer (26 Sep 2026)

Sat, 26 Sep 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

Bay 2-Day Sail #5 (no night sailing) (03 Oct 2026)

Sat, 03 Oct 2026 13:00:00 GMT

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

Bay Catamaran 2-Day with Sailing at Night (17 Oct 2026)

Sat, 17 Oct 2026 14:00:00 GMT

Bay Catamaran 2-Day Sail with Sailing at Night

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

This event is a 2-Day with sailing at night 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 crew. This is a social sail for gain experience sailing on the Bay during the day and night while enjoying time together.

Boat: Second Sight, Seawind 1260 Catamaran

Skippers: Jonah Brewer

POC: Bay Commodore at baycommodore@pentagonsailing.org

Bay 2-Day Sail #6 (no night sailing) (24 Oct 2026)

Sat, 24 Oct 2026 13:00:00 GMT

Bay 2-Day Sail

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

Boat: Serenity, Jeanneau Sun Odyssey 379

Skipper: Marco Ovando

POC: Bay Commodore at baycommodore@pentagonsailing.org