The Best Sailboat Rentals Near Edgewater

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.

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

Captain Bill offers the best value boat charter in the annapolis area, in my opinion. My wife and I chartered captain bills boat (through getmyboat.com) to celebrate her birthday and we had a wonderful time. You can participate as much or as little in the actual sailing as you prefer. There are several comfortable areas on the deck to lounge and catch some cosmic rays, and a salon below deck if you need to beat the heat. BYOB, BYO-snacks, bill provides the ice, water, coozies, and jokes. Very fun charter, would recommend to a friend

Experience the Serenity of Sailing SV Magic

We rented Josh’s boat to do our engagement pictures! He was helpful with timing to catch the best sunset and navigated the boat so our photographer could get the best shots. There was room below for outfit changes and speakers on board to enjoy our time!

Experience the Serenity of Sailing SV Magic

Had a fantastic day sailing with Josh! He was great with communications and was ready to go when we got there. The boat is very comfortable and while we only did a 3 hour sail, the boat has a good galley and bathroom and would be great for a longer sail. The marina location is excellent and we were in the Chesapeake in 15 to 20 minutes. Josh was a great captain - we enjoyed chatting with him and he made us very comfortable. Highly recommended.