Incredible sailboat rentals in Chesapeake Bay, United States.

Sailing Reviews in Chesapeake Bay

1. KC

   Kevin

   April, 2024

   Charter 42' Lagoon Catamaran in Annapolis, MD

   Adam Yearwood is a fantastic captain! His boat is beautiful and he is well organized. We did a team outing sailing around the Chesapeake and had an awesome time - I highly recommend working with Adam!

2. KC

   Kevin

   April, 2024

   41' Lagoon Catamaran in Maryland

   Captain Jess was fantastic! Great experience!

3. JD

   Josiah

   July, 2022

   2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

   Didn't believe we still have such wonderful people. Captain Dash and his co-captain are amongst the very best. Good service, friendly, timely, and most importantly, people Centered. My wife, kids, and I enjoyed riding with this team and we will always wish to ride with them.

4. EM

   Erin

   October, 2021

   Chesapeake Bay Sailing Charter - 33' Cape Dory sailing from Kilmarnock, Virginia

   Our trip was just perfect. We were looking for a true sailing experience, and Captain Russ gave us that. My husband was at the wheel almost the entire trip, talking all things sailing Capt Russ. Meanwhile I enjoyed the sun and sounds of the water against the boat and the wind in the sails from up front. It was a peaceful and enjoyable trip, despite the wind giving out on us towards the end. We'd book with Captain Russ again in a heartbeat!

5. 

   Thomas

   August, 2020

   Chesapeake Bay Sailing Charter - 33' Cape Dory sailing from Kilmarnock, Virginia

   Captain Russ was just ideal for our half day on the bay! Super pleasant and communicative; completely adaptive to whatever we were up for. The Joie de Vie is ship-shape and the perfect vessel for the Chesapeake Bay. I’ll go ahead and credit him with steady 5-6k winds All day also- just a perfect day. No doubt we will be back for more- thanks again, Captain Russ!

6. 

   Ben

   August, 2023

   41' Lagoon Catamaran in Maryland

   Jess was a great captain! We hosted my wife’s 30th birthday party with Jess and it was a great time! His catamaran fit all 12 of us with no problem. He was attentive to the things she wanted to do and was knowledgeable about the area. We had a awesome day on the water with Captain Jess. Would definitely go again!