The Best Sailboat Rentals Near Saint Michaels

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

Ian and Kim were fantastic hosts, captain and first mate! We used Ian’s vessel for a music video shoot, and not only were they helpful and accommodating, but happy to have us aboard and a part of our production. I highly recommend booking with Ian for a similar situation or if you just wanted a fun outing with some good friends!

Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

We booked this experience for my husbands birthday and it was PERFECT! The Selina II IS STUNNING, and Captain Iris and her crew were absolutely wonderful. Captain Matt was fantastic! He took such good care of us while we sailed across the Chesapeake Bay and celebrated with a couple of glasses of delicious champagne! Look no further and book the Selina II, you won’t regret it, it’s absolutely worth it !!

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!

Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.

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!