The Best Sailboat Rentals Near Chester

38-ft Hunter 376 Sailing Adventure in Annapolis

Wonderful Captain and wonderful boat! Plenty of shade above and below deck if the August heat becomes too much. We did the three hour tour, and it was a great half day length. We received a tour of downtown Annapolis and then Captain Alberto opened up the sails and we went on a beautiful ride down the river. It was fun and unique - even for those who have motor boat experience. Sailing is quintessential Annapolis and Captain Alberto was a great host.

38-ft Hunter 376 Sailing Adventure in Annapolis

We went out for an afternoon sail with Capt Alberto and had an amazing time. We were blessed with a beautiful sunny day with perfect wind. Capt Alberto shared interesting stories and taught us a good bit about sailing along the way. Highly recommend!

38-ft Hunter 376 Sailing Adventure in Annapolis

Captain Alberto and his wife are absolute jewels! We sailed with them a couple of years ago and were excited to have this time with them today. They are friendly, professional and just such a joy to be around. Will be seeing them again soon, for sure!

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!

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

We simply loved our three days sailing excursion of the Chesapeake bay. The boat Icarus is very comfortable to maneuver and to live in for a family of four. The bay has numerous nice coves and spots were to stay for the night. Mr James help has been crucial for maximizing our time and energies on these limited days. Thank you Jiim!

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

One of the best sailing weekends we have ever experienced! The boat is manageable and in great shape! James is a great host, he explained everything when we got there, suggested an amazing route and was there when we got back to make sure everything went well. 100% recommended, we’ll definitely rent it again!