The Best Sailboat Rentals Near Hamilton

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!

Woman-owned luxury with transparent pricing - read our 5-star reviews!

Highly Recommend!!! Jessica was very responsive and helpful with helping me plan our last minute sailing. Everything was exactly as described. The ship was clean with nice amenities for our entire party. Captain Kevin was extremely knowledgeable and provided a great experience with plenty of photo opportunities! We can’t wait to do this again!!

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!

35ft C&C 35 Sailboat in Toronto

It was a great experience for me and my whole family. Peter made us a part of sailing experience and my husband and our teenagers gladly participated in everything that needed to be done and also enjoyed the conversation and the company of the captain. Thank you, Peter!