The Best Sailboat Rentals Near Toledo

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!

Sailing Catamaran along Chicago's Lakefront 6ppl $450hr. Captain included.

Another Great Day on the Water This was my second trip with Captain Russell, and it won’t be my last. The boat is better than advertised — super clean and comfortable. Captain Russell just makes it easy. He knows what he’s doing, keeps everything relaxed, and makes you feel like you’ve got your own personal captain for the day. Always a great time out on the lake with him.

Sail & Swim from a Luxury Sailing Yacht

We had a great experience with Captain Greg. The boat was very nice and clean, and we had a great sunset sail! Our kids loved their first sailing experience. Captain Greg even taught my 9 year old how to steer and let all 3 kiddos help with hoisting the sails. Couldn’t have asked for a better night in Chicago!

38-ft Hunter 376 Sailing Adventure in Annapolis

We thoroughly enjoyed our time with Alberto and his wife, Grace. Alberto is a delight to sail with - we learned so much from him. Grace is so lovely and gracious. We sailed around Annapolis during Memorial Day weekend and the weather was perfect. Alberto was very accommodating and friendly. We hope to see you again soon!

38-ft Hunter 376 Sailing Adventure in Annapolis

Captain Alberto is a wonderful Captain. Handles the boat with an expert confidence and was also a willing and kind teacher to my two kids who had millions of questions.

Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!

Was an incredible, beautiful, and relaxing trip on the water. Demi is a wonderful and chill captain and knows all the best spots in the area and I'd defiantly take another trip with him again!