The Best Boat Tours in Maryland

Exclusive Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch

Highly highly recommend booking with Stephen! We had friends coming to visit from out of town and we had the most wonderful charter. Stephen was an excellent captain and very kind host. The boat itself is very cool, with plenty of room to hang on the bow (and a clean bathroom!). Can’t say enough about what a great time we had!!

Enjoy your magical moments with a VIP experience

We had an amazing time celebrating my mom's 50th birthday! The host and crew were friendly, professional, and made the entire experience so much fun. The yacht was beautiful, and everything, for the most part, went smoothly. My only suggestion would be to clarify the pickup location before the trip, as the system-generated address was different from the actual departure address. Other than that, it was a fantastic experience.

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!

Exclusive Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch

Not sure I can say enough about how absolutely incredible our experience was with Steve. Boat was perfect. Communication was perfect. But the experience was incredible! He took my wife, two sons and I out to the Wednesday night races in Annapolis, and we got to engage right into the races, feel the speed of the boats, see the tight turns, and it’s an experience my sons will not forget. Can’t recommend highly enough.

Enjoy your magical moments with a VIP experience

Captain Rod was super straightforward and great at communicating even throughout confusion. Very timely and easy-going in terms of what you decide to do on the boat, music, vibes in general! I want to shout out the host that was there as well she did an amazing job by making us feel comfortable, bringing drinks for us, and answering all of our questions.

Exclusive Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch

Stephen was wonderful! A few days before our sailing trip, the weather forecast looked questionable, but he stayed in touch the entire time, offering to start earlier or even reschedule for a different day if needed. He was incredibly flexible and genuinely wanted to make sure we had the best possible experience. Thanks to his communication and commitment, we had a fantastic trip. I highly recommend sailing with Stephen!