The Best Sailboat Rentals Near Cleveland

38-ft Hunter 376 Sailing Adventure in Annapolis

Alberto and Grace were the perfect team. They are kind, knowledgeable, respectful, communicative, safe and I would recommend them to anyone. This was our first time sailing in Annapolis, and we could not have asked for a better experience. We hope to share future experiences with them. Everything was perfect.

Affordable Yacht 27' Doral in Toronto

Had an amazing experience on the yacht — but honestly, the real highlight was the captain. Super friendly, very patient, and knew exactly where to go for the best views and photos. Even when we were running late, he didn’t rush us at all and made sure we still got the full experience. You can tell he genuinely cares about giving people a good time, not just finishing the trip. If you’re booking this, you’re in safe hands. Highly recommend.

Sail in downtown Toronto

Amazing trip. Would put 10 stars out of 5. Dom is a great captain, absolutely recommend

38-ft Hunter 376 Sailing Adventure in Annapolis

This was our 2nd sail with Capt Alberto. He is super friendly and easy to talk with. And he invites his guests to take an active role in sailing, or to just kick back and relax if they prefer. Great experiences for our family.

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

This is a great boat and we had an absolute blast. worth every penny!

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

Great boat and great value. She still sails beautifully and we had some great wind to prove it. A little aged around the edges, but everything that counted was great.