The Best Sailboat Rentals Near Gloucester Point

AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch

Highly highly recommend booking with Stephen! We had friends coming to visit from out of town and we had the most wonderful charter. Stephen was an excellent captain and very kind host. The boat itself is very cool, with plenty of room to hang on the bow (and a clean bathroom!). Can’t say enough about what a great time we had!!

Relax, feel free & sail into a nautical world of Wonder - Hunter 36 Sailboat

Hi Captain Anthony, we had such a wonderful, relaxing, exhilarating experience sailing with you. It adds to our pleasure realizing that you seemigly had just as much pleasure sailing your beautiful sailboat. It was such a good time for all! I hope to do it again. Thank you

AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch

Not sure I can say enough about how absolutely incredible our experience was with Steve. Boat was perfect. Communication was perfect. But the experience was incredible! He took my wife, two sons and I out to the Wednesday night races in Annapolis, and we got to engage right into the races, feel the speed of the boats, see the tight turns, and it’s an experience my sons will not forget. Can’t recommend highly enough.

38-ft Hunter 376 Sailing Adventure in Annapolis

Captain Alberto and Grace were incredibly welcoming and accommodating during our time on their boat. Captain Alberto taught us all about sailing and we really enjoyed being involved with helping sail the boat. My friend group had such a great time; would recommend! We will definitely be back!

One & Only - 52 Foot Luxury SeaRay Yacht, Brooklyn Bridge Park!

Sorry for the very late review! I took this boat ride about 3 years ago, and it was such an amazing experience. The views were beautiful, the ride was relaxing, and I had a great time. Gene and his crew took care of us and made my sisters party amazing. Highly recommend!

Charter 44' Orana Cruising Catamaran In Deale, Maryland

Had a group with me and they had a blast. Weather started as misty and then became wonderfully sunny along the way. Hoping to see some sea life but alas none waves were pretty choppy. Boat was wonderful.