The Best Yacht Rentals in Annapolis

Private Yacht Charter: On 40ft Regal Commodore

GREAT experience!!! Captain Dennis was terrific. He was professional, yet fun & extremely well prepared. The yacht was clean & well maintained with all the amenities that we could ask for. Our only regret is that we did not book a longer cruise on Seas the Day.

Private Yacht Charter: On 40ft Regal Commodore

Captain Dennis was exceptional—punctual, professional, and allowed us to have a great time. The boat itself was in perfect condition, with all the necessary equipment and some luxurious extras, like the floating 🏝️, that made the day truly enjoyable. The excellent service and the beautiful setting made it an unforgettable birthday party. I highly recommend Captain Dennis for anyone looking to host a memorable and top-notch maritime event.

50ft Catamaran Charter with Water Toys - Annapolis, MD

Captain Deren and the crew were amazing — they made my birthday so special. They were super accommodating the entire day for everyone! They were even kind enough to put up some birthday decorations for our group. I’m definitely going to be booking with Captain Deren again!

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

We had a wonderful time at Captain McCoy’s boat. The boat is gorgeous, impeccably clean, and very spacious. The Captain played great music (we didn’t bring our own playlist). He found a great spot for our group to take a swim. It was a perfect balance of cruising and swimming and a perfect 2 hr cruise

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

Took my husband on a surprise boat ride for his birthday and he loved it!! McCoy was great at communication when I had questions. He took us on a 2 hour boat ride and made the trip so enjoyable and relaxing!! He played music for us and took us to see some beautiful sights. I will definitely be booking all my boat rides with McCoy in the future!

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

We had a great experience with Captain McCoy and his boat. He definitely went the extra mile and was easy to communicate with to set up our trip. We went out of City Dock and toured the coastline, saw Chesapeake Bay bridge and then tied up for some swimming. He had a great float for the kids, and he had some comfy seats for the front of the boat. The shaded table in the back was awesome. Would highly recommend!