Annapolis, Maryland Boat Rentals & Yacht Charters

Annapolis Reviews

1. SY

   Sarah

   Cruise The Annapolis Area Chesapeake on a Classic 46’ Downeast – Up to 25 Guests

   The boat and crew were perfect for a bachelorette party! Captain Steve and Sarah couldn’t have been nicer or cooler throughout the ride. They were very accommodating and were on top of communicating, especially with the possibility of bad weather. The day and process couldn’t have gone better!

2. 

   Lauren

   Charter 42' Lagoon Catamaran in Annapolis, MD

   We had an amazing day on the bay with Captain Adam! He was super communicative leading up to the trip, providing amazing instruction to make it as easy as possible to get aboard. While on board the vessel was very clean and comfortable and he and his team were knowledgeable about the area. Highly recommend! They’re lovely!

3. DC

   Donte

   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!

4. AH

   Abby

   Big Thrills, Big Water, Big Fun — Introducing the 24′ Hurricane Sundeck

   A wonderful boat day! I would recommend Griff and use him again!

5. JA

   Joey

   Enjoy the best views of Annapolis, MD aboard this beautiful Lydia dinner yacht

   Booked a private yacht charter along the Island Princess for 3 hours and had a great experience! Captain Steve was kind, accommodating, and knowledgeable during our journey! Would 100% recommend! Thank you!

6. KC

   Kevin

   Charter 42' Lagoon Catamaran in Annapolis, MD

   Adam Yearwood is a fantastic captain! His boat is beautiful and he is well organized. We did a team outing sailing around the Chesapeake and had an awesome time - I highly recommend working with Adam!