The Best Boat Rentals Near Saint Michaels

38-ft Hunter 376 Sailing Adventure in Annapolis

Captain Alberto and his wife are absolute jewels! We sailed with them a couple of years ago and were excited to have this time with them today. They are friendly, professional and just such a joy to be around. Will be seeing them again soon, for sure!

2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

Dushaune was amazing! The best boat ride we have ever had. He is extremely nice and drove us to a swimming area that was amazing. We enjoyed just hanging in the water, talking with him. We lost track of time because we were having so much fun. Would definitely love to go on a ride with him again.

Private Yacht Charter: On 40ft Regal Commodore

Captain Dennis was an amazing host. We came with a group of 10 and everyone had an amazing experience. The boat is amazing and Captain Dennis will make sure you have a great time!

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!

2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

Everything about the trip was great. The captain was in great communication from the booking to the day of our trip, and provided great customer service. We will definitely be booking again!

2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

Dushaune is a great captain and great host, he is down to earth, knowledgeable, funny. We are a group of 6 with very different characters and age (from 7-50) but all of us had fun. We felt great after the ride. Thanks Dushaune. Highly recommended