Great sailboat rentals near Annapolis, Maryland.

Sailing Reviews in Annapolis

1. MI

   Maria

   June, 2024

   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!

2. 

   Jordan

   June, 2024

   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!

3. DH

   Daniel

   June, 2024

   38' Hunter 376 Cruising Monohull in Annapolis, Maryland

   We had a great time with Alberto and Gracelia. The boat was well organized and well maintained. They walked us through the proposed route and adjusted it according to our interests. Because we were interested, Alberto was happy to explain all the elements of saling and let family members take the helm. Also, very nice that Alberto speaks English, Spanish and Portuguese. Parkin was clear and easy.

4. CB

   Caprice

   June, 2024

   41' Lagoon Catamaran in Maryland

   This was one of the best rides I’ve had in a while. Captain Jess is communicative, helpful and kind. We went out for 4 hours and had great weather. The boat is clean, he had 2 fridges for our food and drinks, it was nice and spacious, and there were floaties to get out on the water. It was a very enjoyable day.

5. SS

   Steven

   June, 2024

   38' Hunter 376 Cruising Monohull in Annapolis, Maryland

   Captain Alberto took 4 of us out for an exciting day on the Chesapeake. He and Grace were most friendly. He is a very experienced sailor. The boat is in very good condition. Everyone had a wonderful time.

6. DB

   Dan

   May, 2024

   38' Hunter 376 Cruising Monohull in Annapolis, Maryland

   Capt Alberto and Grace were wonderful hosts. They were very flexible regarding the weather, great teachers of sailing, and were very hospitable and welcoming with their boat. We had an amazing time. Capt Alberto truly loves the sea.