The Best Sailboat Rentals Near Virginia Beach

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!

Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!

Was an incredible, beautiful, and relaxing trip on the water. Demi is a wonderful and chill captain and knows all the best spots in the area and I'd defiantly take another trip with him again!

Sailing NYC aboard 34' Catalina

Ian provided us with a fantastic sailing experience for our wedding anniversary. It was absolutely lovely—truly beyond our expectations. His communication and instructions were clear and outstanding from start to finish. On the day of our sail, Ian even reached out to offer an earlier time slot when one became available, which we appreciated. The boat was perfect, and we had an unforgettable time on the water. Thank you, Ian, for making our special day even more memorable!

Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.

we did our engagement pictures on the boat & everything was great! Bill was super cooperative & made sure we got all of the best spots for pictures! highly recommend!

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

What an enjoyable experience! Captain Joe was always attuned to our wishes, making an extra effort to make this afternoon pleasant for all. His company is very agreeable. We wish we could relive yesterday's feeling of complete relaxation over and over!

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

Sarah was helpful in lining me up for a sail boat for Mothers Day and in recommending a captain and in adjusting time to meet our needs.