Call 410-939-2869 to Book your charter or daysail!

Please Note: If you have not chartered with BaySail before, you will be required to fill out and return a CHARTER APPLICATION form prior to approval of your charter.

DaySail/Charter Application Form

Charter from BaySail …and enjoy the very best in service and quality sailing vessels. Named “Best of the Bay” for yacht charters by Chesapeake Bay Magazine, BaySail offers fully equipped, new or recent model yachts designed for comfort and ease of sailing. BaySail also has an excellent selection of smaller sailboats available for half day and full day rental. Regardless of your selection, you can rest assured that all BaySail boats are sparkling clean and impeccably maintained. And, because of our convenient location just off I-95 in historic Havre de Grace, you will be driving less and sailing sooner if you choose to charter with BaySail. Charter the Chesapeake… and enjoy sailing one of the world’s finest cruising grounds. Whether you are in the mood for a fine dinner at a bustling harbor or a quiet day in a secluded cove, the Bay offers enough attractive and interesting cruising spots to keep most sailors busy for a lifetime. BaySail offers a choice of bareboat, captained or instructional charters. A full range of sailing courses is also available, all of which are certified by the American Sailing Association (ASA). ASA certification ensures that our school complies with an established and comprehensive program. Plus, ASA certification is recognized worldwide by sailing professionals and yacht charter companies.

22' Daysailers

Known for their sweet sailing performance in nearly all conditions, the Capri  and Cal 22s have been winning the hearts of sailors for generations! These 22s have a comfortable cockpit and a full cabin with seating for five.

Hunter 29.5 - Hazel Rose

Our Hunter 29.5 is a great cruiser with two cabins, and a spacious and roomy salon. Features include a roller furling jib and a full batten main.  Amenities include a large cockpit, walk-thru transom with swim platform.

Beneteau Oceanis 41 - Pegasus

The Oceanis is a very comfortable vessel with plenty of extra equipment to make your week or weekend a perfect vacation. With two helms, three cabins, and a large salon, this boat is perfect for extended cruising down the bay.

Gemini 35' Catamaran - 14 Hands

This new model Gemini catamaran is a perfect size boat for the Chesapeake Bay. Maneuvering is easy with twin diesel engines and a fourteen foot beam. This boat has a super spacious cockpit and a full enclosure to protect from the weather.

Hunter 33' - Chances R and No Name

If you are looking for a compact cruiser these Hunters have all the bells and whistles. A great boat for the bay that is easy to sail in both heavy and light air.