The Best Sailboat Rentals in Annapolis

Experience the Serenity of Sailing SV Magic

We rented Josh’s boat to do our engagement pictures! He was helpful with timing to catch the best sunset and navigated the boat so our photographer could get the best shots. There was room below for outfit changes and speakers on board to enjoy our time!

Experience the Serenity of Sailing SV Magic

Had a fantastic day sailing with Josh! He was great with communications and was ready to go when we got there. The boat is very comfortable and while we only did a 3 hour sail, the boat has a good galley and bathroom and would be great for a longer sail. The marina location is excellent and we were in the Chesapeake in 15 to 20 minutes. Josh was a great captain - we enjoyed chatting with him and he made us very comfortable. Highly recommended.

Experience the Serenity of Sailing SV Magic

We had an awesome trip with Josh. He was very flexible with timing and knowledgeable about sailing. We were able to take our engagement photos on Josh’s boat with his help and input on lighting/backgrounds. It was a wonderful experience we will never forget!

50ft Catamaran Charter with Water Toys - Annapolis, MD

Captain Deren and the crew were amazing — they made my birthday so special. They were super accommodating the entire day for everyone! They were even kind enough to put up some birthday decorations for our group. I’m definitely going to be booking with Captain Deren again!

38-ft Hunter 376 Sailing Adventure in Annapolis

Our family of four, who are experienced sailors, appreciated the opportunity to sail with Alberto and his lovely wife, who shared lots of great stories and reflections of sailing on the Bay. The boat was perfect for a day of sailing, and exactly how described on the website. It was clean and comfortable and we felt completely welcomed, and were able to participate in sailing activities as we desired, while also relaxing and enjoying some downtime. Great time sailing!

38-ft Hunter 376 Sailing Adventure in Annapolis

Our sailing trip exceeded our expectations! Captain Alberto is a complete treasure: he shared his sailing knowledge and involved us in the sail as much as we wanted - The boat was clean and comfortable with space to enjoy the trip both above and below deck. We only had 2 in our party, but 6 people would absolutely be comfortable given the space. We hope to book a trip with Capt. Alberto again!