Incredible sailboat rentals in Chesapeake Bay, United States.

Sailing Reviews in Chesapeake Bay

1. LP

   Laura

   38-ft Hunter 376 Sailing Adventure in Annapolis

   Captain Alberto and his wife are absolute jewels! We sailed with them a couple of years ago and were excited to have this time with them today. They are friendly, professional and just such a joy to be around. Will be seeing them again soon, for sure!

2. DC

   Donte

   New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

   From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!

3. GA

   Giselle

   38-ft Hunter 376 Sailing Adventure in Annapolis

   Capt. Alberto and Graciela, the best! We had a great time and enjoyed learning about sailing with them. Everything was as described and much better. You’ll have a great time too! ⛵️☀️🩵

4. QT

   Quang

   Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

   been through a few yacht but Joe is the best host. He makes sure you will have a wonderful trip. And his boat is gorgeous, clean and spacious!

5. 

   Marie

   38-ft Hunter 376 Sailing Adventure in Annapolis

   We thoroughly enjoyed our time with Alberto and his wife, Grace. Alberto is a delight to sail with - we learned so much from him. Grace is so lovely and gracious. We sailed around Annapolis during Memorial Day weekend and the weather was perfect. Alberto was very accommodating and friendly. We hope to see you again soon!

6. 

   Sam

   38-ft Hunter 376 Sailing Adventure in Annapolis

   Captain Alberto is a wonderful Captain. Handles the boat with an expert confidence and was also a willing and kind teacher to my two kids who had millions of questions.