Browse Chesapeake Bay Boat Rentals.

Chesapeake Bay Reviews

1. HS

   Halle

   Cruise DC and turn heads aboard the vintage 1985 Chris Craft, American Pie

   Highly recommend American Pie with Weston and crew! The boat is spacious, clean, and beautiful — the perfect way to take in the DC views along the Potomac. Anna was our captain, and she was absolutely awesome. We even took our engagement photos onboard and had the best time!

2. LB

   Liara

   Sanpan 2500 RE Pontoon in Washington, Living room comfort on the water!

   We had such a wonderful time celebrating my birthday with Captain Mike! His communication was excellent, he arrived more than in advanced time, and he made the whole experience smooth and enjoyable. While we were playing a game onboard, he jumped in with the perfect answer—“buy a boat if we win the lottery”—which had everyone inspired. Captain Mike struck the perfect balance of professionalism and friendliness, and he truly made my day memorable. Highly recommend!

3. WB

   Winnie

   Take your Sailing Dream on Chesapeake Bay. Rates reduced to for that dream!!

   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!

4. AH

   Angela

   Take your Sailing Dream on Chesapeake Bay. Rates reduced to for that dream!!

   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!!

5. NC

   Nick

   Take your Sailing Dream on Chesapeake Bay. Rates reduced to for that dream!!

   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.

6. 

   Michael

   Take your Sailing Dream on Chesapeake Bay. Rates reduced to for that dream!!

   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