Sailboat Rentals

Making the Reservation

A reservation is needed to make sure a sailboat is ready when you want to sail. You must call us to confirm sailboat availability and weather conditions that permit rental.  The rental day is from 9:00 a.m. until 4:00 p.m. A late fee is charged for boats returned after 4:30 p.m. The half day rental is 4 hours. Call 800-638-9192 to make a reservation, confirm sailboat availability and/or check if weather conditions are good for rental.  


$250 per day (includes insurance) - 9 am – 4 pm

$160 per 1/2 day (4 hours) - 9 a.m. – 1p.m. OR 1 p.m. - 5 p.m.

Annapolis Sailing School Graduates Discounted Rate*

$225 per day weekends$125 per day weekdays

*no discounts on holidays


Our sailing fleet consists of fiberglass sailboats called Rainbows designed by the finest naval architects and built to the highest standards. They are equipped and ready to sail. It is your responsibility to return these boats in the same condition in which you found them. The Rainbow cockpit is surrounded by a large coaming design to keep you dry when the spray flies. The strong fiberglass hull and deck make the boat virtually indestructible. An 1100 lb. cast iron keel provides immense ballast when the wind picks up and serves to keep the boats upright and dry.


The Rainbow has an exceptionally large cockpit with comfortable seating and backrests, on the premise that sailing should not be a cramped, hunched up affair. This high degree of comfort and safety has earned the Rainbow the reputation for being one of sailing's most seaworthy craft.


The Rainbow is long and lean. It possesses fine, clean lines that cut through the water with authority. While the novice will appreciate its responsiveness from the start, admiration for its speed and agility grows with experience. In fact, its designers have ever so successfully combined the Rainbow's characteristics of a comfortable daysailer and one design racing sloop. Rainbows are actively raced throughout the United States and each year the home port of one of the larger fleets hosts the championship.

rentalsSailing Area

We restrict our rentals to an area bounded by Greenbury Point to the north, Tolley point to the south, a line between these two forms our eastern boundary, and the Naval Academy Seawall to the west. Portions of the Severn River offer you a splendid view of the Naval Academy. Boundaries, determined by management, are subject to change depending on conditions at the time of your rental. If you wish to familiarize yourself with the area before you sail, obtain Nautical Chart #12271. Please understand that going beyond these boundaries make quick retrieval of the boats in case of weather changes problematic (ie. pop up thunderstorms or calm wind conditions).  Late returns of boats due to venturing beyond boundaries will result in significant charges or revocation of rental privledges.


If small craft advisories are flying at the beginning of the rental, it may be postponed, or canceled at the discretion of the management. Call ahead if at all possible to check weather conditions (the weather can be very different from points inland).


Our boats are covered 100% by insurance. Please inform management of any damage that occurred during the rental. The Lessee has no liability for repairs. However, Annapolis Sailing School  is not responsible for personal injury or damage to other boats. You should check your own insurance coverage.


Our sailboats are equipped with all necessary safety equipment to meet Coast Guard regulations. However, we do not have personal flotation devices for infants. Good seamanship dictates that infants not be taken aboard any vessel. We remind you that it is your responsibility to check this equipment before leaving the dock. No pets are allowed on our boats. There is a minimum of two persons required for safe handling of the boat.


Weather Forecast

Light rain



Light rain
Wind: N at 8 mph
49°F / 53°F
42°F / 55°F
38°F / 49°F

Current Conditions

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