Our Fleet


At Annapolis Sailing School our commitment to relaxed, enjoyable sailing is reflected in the sailboats that we use in our classes. Although the Rainbow is considered a classic design, we have not found a boat that works better as a basic trainer. Thousands of beginners have tasted that first thrill of sailing on a Rainbow over the decades and have gotten hooked from there. Two important considerations in any training boat are safety and comfort. Safety Rainbows will heel (lean over) but they will not capsize (tip over)! We know from experience that capsizing is the number one fear of adult beginners. The Rainbow’s design makes her unable to capsize. In addition, the boat’s simple rig enables everyone to sail while remaining in the cockpit, seated in comfort and well below the boom. USCG-mandated safety equipment is aboard all of our boats and PFDs are provided for all sailors from children to adults. Feel free to bring along your own PFD if you wish. Comfort With four adults in the cockpit, there is still ample legroom for everyone. The seats are chair height and the high cockpit coaming (edge) offers comfortable back support. Visibility is excellent in all directions and the simple, uncomplicated rig means a minimum of clutter and gear in the cockpit. The small cuddy cabin was designed to provide excellent protection from wind and spray when the sailing gets really interesting! Variety Several versions of Rainbows have been made over the years and we have two varieties in our fleet. The original Rainbow makes for a sporty ride while the Knockabout gives up the forward cabin to create a much more open cockpit for a roomy seating area.

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Beneteau 37

The Beneteau 37 is an outstanding mid-size cruiser. From her easy-handling but powerful rig complete with a mast-furling mainsail and roller-furling jib to her wide cockpit with walk-through transom and swim ladder, and fresh water shower, the 37 is a boat designed to maximize cruising pleasure. Step below into her cavernous main salon and enjoy a full galley with double stainless steel sinks, a front-loading refrigerator, a propane stove with oven, a microwave, and more storage space than you can imagine making meal preparation a breeze. The cabin layout features two airy and bright private staterooms as well as convertible berths in the main salon. The fit and finish on all the wood is equal to what one would find on custom yachts costing much more. A full head with a separate stand-up shower and six and a half feet of standing headroom ensure your comfort, whether you are on board for an overnight or just a day cruising experience.

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Sabre 34

Designed and built-in Maine, the Sabre 34 is a boat that sails as well as it looks. Designed as a cruiser/racer, the double spreader rig gives the boat ample power that is easily handled by the well-balanced helm. The wing keel allows for upwind ability and anchoring in your favorite gunkhole. The updated B&G instruments mate to a full-size chart plotter at the helm so you always know where you are. She sleeps 6 comfortably with a pull-out double berth in the main saloon, forward V berth, and aft double berth. The four dorades and two hatches keep it breezy and comfortable down below. A working oven, two-burner stove, and refrigerator allow you to play boat-gourmet at the spacious fold-down table while the full head and shower keep the crew clean.

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Caraluna 245 by Tartan

The newest addition to our fleet. The famed boat designer Tim Jackett in collaboration with instructor Cai Svendsen has built a 24-foot boat that is comfortable for up to 5 sailors in the cockpit plus an instructor. Conceived as an educational platform, the boat is very tunable consisting of a fractional rig, adjustable backstay, cunninghams, halyards, boom-vang, and outhaul, which all run to the cockpit for easy accessibility. A cushioned V berth provides refuge from the sun and comfort for the little ones. The boat performs well upwind and excels under a spinnaker in a breeze - surfing at 15 knots. It is a great educational tool for our racing and spinnaker classes, and our KeelBoat Club members love it as a daysailer.

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