Incredible sailboat rentals in Chesapeake Bay, United States.

Sailing Reviews in Chesapeake Bay

1. RB

   Richard

   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.

2. SF

   Sierra

   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!

3. LF

   Linda

   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!

4. RM

   Richard

   38-ft Hunter 376 Sailing Adventure in Annapolis

   Capt. Alberto and his wife were awesome hosts! They were totally flexible about our schedule and it was great to hear about his prior sailing experiences. It was great to be with such an experienced host! We will definitely book with them in the future!!

5. MK

   Michael

   38-ft Hunter 376 Sailing Adventure in Annapolis

   Capt Alberto is great. Very knowledgeable and very pleasant. He lets you participate in manning the boat as much as you want and is especially good and introducing new sailors to the glorious activity. Highly recommend!

6. MB

   Maya

   38-ft Hunter 376 Sailing Adventure in Annapolis

   Capt Alberto and his wife were SO AMAZING!! They taught us how to sail and we sailed across the Chesapeake. Their boat is beautiful and their company is great. I highly recommend everyone book if they are looking to sail in the Annapolis area for a few hours, learn about sailing, and have a relaxing time.