No trip to the sailing capital of America would be complete without getting out on a sailboat.. Our fleet of Rainbow 24s provides a safe and fun experience for those looking to have a relaxing time on 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.


Weekdays – $175 for a full day or any portion of a day between 9 am – 4 pm.

Weekends and Holidays – $250 for a half-day between 9 am – 12:30 pm OR 1:00 pm – 4:30 pm


A reservation is needed to ensure that a sailboat is available when you want to go out. 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.

A late fee of $50 will be charged per half-hour overdue.

Call 410-267-7205 to make a reservation.


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.

Qualified Renters

At least one person in the rental party needs to have an ASA 101 certification or its equivalent or needs to complete a sailing competency evaluation with us prior to their first rental. Renters are required to rig and de-rig their boat. The Rainbows do not have engines so sailors must be able to depart and dock under sail.

Sailing Area

Rentals are restricted to an area close enough to the school so that help can 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 case of emergency. Late returns of boats due to venturing beyond that day’s boundaries will result in late fees. If a renter goes outside the proscribed sailing area and needs to be retrieved, there will be a fee of $75 and the renter will be unable to rent with us in the future.


Sailing is entirely dependent upon wind and weather. We recommend that renters check three days before the rental date to see what the forecast is for that day. If small craft advisories or worse are in effect at the start of the rental, the rental may be postponed or canceled at the discretion of the management. In that case, the rental can be rebooked at no additional cost. In low wind situations, you will need to plan your sail so that you can be back at the dock on time.

Small craft advisories often affect both boundaries and may preclude rental availability. We will not rent when gale warnings are in effect.


Rentals reservations are charged at the time of booking. Rescheduling within three calendar days of the originally scheduled start of the reservation will result in a $50 rescheduling fee per occurrence. Cancellations made within two calendar days of the scheduled day of the reservation will receive no refund. Refunds are not available for lack of wind.


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.

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