Keelboat Club

Be a social sailor

A Beautiful Sailing Season!

Our revamped and enhanced Keelboat Club is ready to welcome members to maximize sailing and socializing in Annapolis. Enjoy Monday night member racing, boating seminars, new social events, a member-matching Facebook page, new boats, and a new clubhouse to relax in!

Member Benefits & Pricing

Level One The Social Sailor

Level Two The Rainbow Sailor

Level Three The Ultimate Sailor

Membership Price




Discount on Courses Social Level - 10% Rainbow Level - 15% Ultimate Level - 20% Courses Discount on Courses

Discount on Rainbow Rentals Social and Rainbow Level - 30% Ultimate Level - 100% Rentals Discount on Rainbow Rentals

Monday Night Racing During the summer months, we hold Rainbow regattas on Monday evenings. Our Keelboat Club members can come for the pre-race chalk talk and strategy session and then head out on the Rainbows for a friendly race. Guests can be approved on a case by case basis. / Call or Email to reserve Monday Night Racing

Free Educational Seminars Free Educational Seminars

Social Events and Parties Events may have different guest policies than general property access. Okay Social Events and Parties

Member-Matching Sailor Network Member-Matching Sailor Network

Daytime Beach and Sail Shed Access Members are limited to one "boat load" of guests or six people including the member Okay Daytime Beach and Sail Shed Access

Two 2-Hour Private Instructions Members can bring up to two other people on their private instructions Rainbow Level - 2 Ultimate Level - 3 Book Private Instruction Two 2-Hour Private Instructions

Unlimited Paddleboard and Kayak Use Unlimited Paddleboard and Kayak Use

Unlimited Weekday Rainbow Rentals Our Rainbow 24 sloops have proven to be nimble, fast, and forgiving. Designed by Sparkman and Stephens specifically for Annapolis Sailing School, the boats are ready to please both novice and experienced sailors. The substantial fixed keel (1100 lbs), cuddy cabin design, and large cockpit combine to produce a boat that is stable, dry, and comfortable. Rentals Unlimited Weekday Rainbow Rentals

Weekend Half-Day Rainbow Rentals Social Level - 1 Rainbow Level - 10 Ultimate Level - Unlimited Rentals Weekend Half-Day Rainbow Rentals

12 Weekday Cruising Boat Rentals 12 Weekday Cruising Boat Rentals

6 Weekend Cruising Boat Rentals 6 Weekend Cruising Boat Rentals

Additional Restrictions: Access to beach and Sail Shed may be limited by private events taking place on the property. Additional restrictions may apply. Please call 410.267.7205 with any questions.