The Best Boat Rentals Near Saint Michaels

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.

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

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

38-ft Hunter 376 Sailing Adventure in Annapolis

Capt. Alberto and Graciela, the best! We had a great time and enjoyed learning about sailing with them. Everything was as described and much better. You’ll have a great time too! ⛵️☀️🩵

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

Amazing! I went with my family, ages 5 and up, and everyone had a fantastic time. Captain Dushaune is a gem - personable, patient, funny, prepared. His boat is beautiful and well maintained. He was laid back while also keeping us safe and happy. He knew the waterways well, took us to a perfect cove for swimming and relaxing. The marina where his boat is located is ideal - clean, easy parking, great views, great water access. I cannot wait to book with him again. Highest possible recommendation!

38-ft Hunter 376 Sailing Adventure in Annapolis

We thoroughly enjoyed our time with Alberto and his wife, Grace. Alberto is a delight to sail with - we learned so much from him. Grace is so lovely and gracious. We sailed around Annapolis during Memorial Day weekend and the weather was perfect. Alberto was very accommodating and friendly. We hope to see you again soon!