The Best Boat Rentals Near Essex

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!!

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.

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!

38-ft Hunter 376 Sailing Adventure in Annapolis

Captain Alberto and Grace were incredibly welcoming and accommodating during our time on their boat. Captain Alberto taught us all about sailing and we really enjoyed being involved with helping sail the boat. My friend group had such a great time; would recommend! We will definitely be back!

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!