The Best Sailboat Rentals Near Selby-on-the-Bay

Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

Sailing with Captain James was a dream!! You will not regret this experience! Not only is he hospitable, he is full of life and passion which only made our trip better. We enjoyed every part of our trip the only sad part was that we didn’t book longer. 100/10 would book with Captain James again!!

38-ft Hunter 376 Sailing Adventure in Annapolis

Our family of four, who are experienced sailors, appreciated the opportunity to sail with Alberto and his lovely wife, who shared lots of great stories and reflections of sailing on the Bay. The boat was perfect for a day of sailing, and exactly how described on the website. It was clean and comfortable and we felt completely welcomed, and were able to participate in sailing activities as we desired, while also relaxing and enjoying some downtime. Great time sailing!

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

HIGHLY recommend Capt Joe for a fantastic sailing experience out of Rock Hall. Joe worked with us to get a last-minute booking when another booking fell through. He and his crew are experts and you will not be disappointed. He let us take the helm and participate as much or as little as we wanted to. Sol Searcher is a beautiful, well-equipped boat - plenty of comfort and speed (wind dependent of course.)

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

Capt. Bill was so accommodating and great with his communication. We had an emergency and he was very understanding. He gave my nine year old great information about the boat and the waters. He and Jonathan were very kind during our charter. It was a great first sail for our family!

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

Captain Bill was absolutely marvelous!! The trip was amazing!! My guest and I chartered a three hour venture and had the wonderful adventure! We celebrated my cousin’s birthday and everyone was elated to ride with such a great captain! He went above and beyond to make sure we had a joyous occasion! His personality was second to none!! I extremely recommend you charter him for your next boat ride!! You will not be disappointed!!

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

Bill was terrific at helping me learn more about handling a 42' sailboat. I'm trying to get more experience in preparation for taking a bareboat charter, and Bill's experience and mentorship was terrific. I look forward to booking with Bill again in the future.