Any trip to the sailing capitol of America without taking a boat out is a missed opportunity. Our fleet of Rainbow 24s provides a safe and fun experience for those looking to have a relaxing time on the water. With views of the U.S. Naval Academy and the Annapolis harbor from the water, feel free to bring lunch and turn it into a picnic as you pass by the sights with the wind carrying you along.


$200/half-day - Either 9 am - 12:30 pm OR 1:00 pm - 4:30 pm (weekends only)

$160/weekday full-day between the hours of 9 am- 4 pm (weekdays only)

Making the Reservation

A reservation is needed to ensure a sailboat is ready when you want to sail. At least two adults are required on a rental boat, one of whom is a qualified sailor. Up to six people are permitted on a rental boat; no children under 5 years of age. No pets are permitted.

The rental periods are listed above. A late fee of $50 will be charged per half-hour overdue.

Book online or call 410-267-7205 to make a reservation.

book now


Our Rainbow 24 sloops have proven to be nimble, fast and forgiving. Designed by Sparkman and Stephens specifically for Annapolis Sailing School in the early 1960s, 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. Rainbow 24s are without auxilliary propulsion, sailors must be able to depart and dock under sail. 

Sailing Area


Rentals are restricted to an area close enough to the school for help to reach you quickly in an emergency situation. Boundaries, determined by management, are subject to change depending on weather and water conditions at the time of your rental. Please understand that going beyond these boundaries makes quick retrieval of the boats difficult in cases of problematic weather changes (ie. sudden thunderstorms). Late returns of boats due to venturing beyond boundaries will result in late fees.


If small craft advisories are in effect at the start of the rental, the rental may be postponed, or canceled at the discretion of the management. If inclement weather is predicted, call ahead to check weather conditions as the weather can be very different from points inland.


The boats are covered 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 before sailing.

kidship-sailing annapolis-powerboat keelboat-club visit-annapolis asa

S5 Box



You need to enable user registration from User Manager/Options in the backend of Joomla before this module will activate.