Chesapeake Sailing Charters


We offer a 3-days-for-the-price-of-2 discount over the weekend. This means you can board on Thursday after 5:00 pm and sail Friday, Saturday and return Sunday for the 2-day rate. No discounts will apply to the Memorial Day, Fourth of July or Labor Day weekends.

Maryland Sales Tax and Anne Arundel County Amusement Tax is also due and payable, 11% total.

Customer Testimonials

Chesapeake Sailing Charters has created lasting memories and happy customers over the years. Please see some of their comments below:

 (Gunter, Rhall and Kathy (all from Minneapolis and Kathy and Victor  – Captain and 1st Mate Falls Church)
“Weather today continues to be hot, humid and sunny, although just as we are leaving it turned breezy and cool, just to make us feel even sadder to leave this beautiful place and beautiful boat…The boat was very comfortable for 5 people, and the Minnesotans were very impressed with the mild swimming temps (much better than Lake Superior! It’s hard to impress us in the Land of 10,000 Lakes but we were!”

 (James, Becky, James & Anne-Marie)
“The boat is top class. She handles beautifully and copes with all the elements and what the skipper can throw at her. We have had no problems.”

(Rick, Erik, Andy, Connor, Robert)
“Sailed out of Choptank with (race groups), then headed northwest towards Deale. Another excellent afternoon of sailing. This is a great cruising boat.”

 (Marilyn Roy Pam & Bob)
“Great trip!!! Really liked the boat, navigational system, large head, kitchen is open and spacious. Thanks for sharing your boat – hope to be back.”

(Rick, Ron, Rob, Nick and Jon)
“All in all, another excellent sailing trip in a good boat.”

(The Oliver Boys: Eddie, Wells, and Lang)
“Great Trip!! Thanks Doug and Vergie!! Boat has everything!!”

​​Early Boarding and Extra Night
Boarding for charters is anytime after 5pm. Sleeping aboard before or after your charter is permitted at no extra charge, but the boat must be at the dock by sundown on the night of your return. Charterers must leave the boat by 10:00 am the following day.

Bed Linens and Towels
Blankets and pillows are provided. Please bring sheets, pillowcases, towels and paper goods.

Boats and Rates

"Romper" is a nicely appointed Hunter 376. It has a roller furling main and jib, powered anchor windlass with washdown pump, air conditioning/heat and microwave oven from shore power,  Northstar chartplotter with Navionics Platinum 3D charts, autohelm, feathering prop, bimini, deck shower with hot water, sea nettle pool and stereo cd player with iPod dock. 

37.5 feet in length
SLEEPSSleeps 6 comfortably