Great sailboat rentals near Annapolis, Maryland.

Sailing Reviews in Annapolis

1. MS

   MoniqueSeptember, 2023

   46' Catamaran Charter with Water Toys - Annapolis, MD

   Deren & Kristal were excellent hosts! We had a lovely day sailing the Chesapeake. They were very communicative and timely with their responses and were flexible with our parties needs and wants. What an excellent experience! Would highly recommend their boat.

2. LR

   LorettaSeptember, 2023

   Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

   What a gorgeous day on the water aboard Sol Searcher! Captain Joe was an awesome host for our day! Peaceful, serene and exactly what we were hoping for to bring the summer to a close. What a lovely world we have to enjoy when we step away from the hustle of life and take the opportunity to take in all that it has to offer. Thank you Capt’n Joe for a wonderful sailing experience. Until we meet again, Loretta and Greg

3. WC

   WhitneyAugust, 2023

   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!

4. JW

   JulieAugust, 2023

   46' Catamaran Charter with Water Toys - Annapolis, MD

   Incredible! Deren and Krystal made our experience phenomenal. From start to finish they were fun and professional. The boat is a stunner! We felt like royalty. My son celebrated his 8th birthday in style with all the toys and had a blast. We will be using them again next year.

5. WB

   WinnieAugust, 2023

   Charter this 42ft Sailboat in Edgewater, Maryland for up to 6 persons MAXIMUM. Take a sail on beautiful Chesapeake Bay or take some Beginner or Advanced sailing lessons on a big boat.

   Capt. Bill was so accommodating and great with his communication. We had an emergency and he was very understanding. He gave my nine year old great information about the boat and the waters. He and Jonathan were very kind during our charter. It was a great first sail for our family!

6. KL

   KatieAugust, 2023

   41' Lagoon Catamaran in Maryland, United States

   Jess was amazing! He arrived early and allowed us to board early. Provided great information upfront and communicated speedily with any questions we had. Made one stop during our 5 hour booking. We had a wonderful time and we highly recommend!!