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. SM

   Shanickia

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

   This experience couldn’t be better! We booked for my sisters 30th birthday.. and had an amazing time. We came with our own decor and food.. but Sarah made the vibes comfortable for us! Def a lit time!

3. 

   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!

4. 

   Ellen

   Private Yacht Charter: On 40ft Regal Commodore

   Dennis and David provided our friends and company with an amazing day. From the initial contact to meeting us in the parking area and taking us to the best location to watch the Blue Angels. We cannot say enough good things about our time with Dennis. The boat was beautiful and very clean. We thank you for providing coolers with water and some other drinks. The kitchen was well stocked to help us set up and serve the food we bought. We can't wait to join Dennis again soon on another adventure!

5. 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!

6. AS

   Angela

   Private Yacht Charter: On 40ft Regal Commodore

   Our trip with Captain Dennis was fantastic!!! The boat is beautiful and we had a lovely time out on the water relaxing with friends. The big blue float was a great addition for when we anchored. Captain Dennis was very communicative and went above and beyond to make the experience a great one. 10/10 would recommend!