See bareboat charter rates for the British Virgin Islands.

Upper Bay Sailing now offers an expanded fleet for both Captained and Bareboat Charters in the Caribbean and on the Chesapeake Bay.

Call our office at 866 380 7245 to make a boat charter reservation.

Click here to see our Chesapeake Bay Sailing Charter rates.

We have greatly expanded Chesapeake Bays sailing charter fleet offer three fantastic yachts. No matter what your Chesapeake Bay sailing charter needs, we have a yacht for you. All of our sailing charter fleet come equipped with pillows, sheets, blankets, towels, and all the charts and navigational gear you'll need for a great charter.

For couples, small families and thoseon a budet, our C&C 29 is perfect. This shoal draft cruiser is the ideal boat for gunkholing and finding the Bay's hidden gems. It features wheel steering, furling headsail, full head with shower and galley and is a fun yacht to sail. The C&C 29 comfortably sleeps 4.

Need a larger yacht or going further? Our Island Packet 40 is right for you. Designed to cross oceans, Island Packets are perfect for a weekend or weeklong cruise. You won't be able to fill all the storage spaces on this boat and the fridge is so large you could crawl into it. Up top, we have a furling headsail, easy slide mainsail, autopilot, full instrumentation and this boat is green -- with LED lighting and and wind generator. The IP can comfortably sleep 6.

Ready for top of the line? Our Benneteau 411 offers a the convenience of a large cruiser with the ammenities of home including air conditioning, wheel steering and furling headsail. The Benneteau also offers a wind generator for your green power management.

Pricing informationfor our Chesapeake Bay sailing charter fleet is contained in the table below.
Vessel details and photos can be obtained by clicking on the vessel type in the table.

Beautiful Green Point Marina

Our chesapeake bay sailing charter home is Green Point Marina. Green Point Marina is located at the mouth of Worton Creek off Route 298 and is about 6 miles North of Chestertown. Our chesapeake bay sailing charter home is a beautiful location and favorite anchorage for cruising boats as well as long distance cruisers going to New England or Florida. Sails can be raised 10 minutes after leaving the dock. There are many excellent cruising destinations close by. The Sassafras River is one of the most beautiful on the Bay and is about 1 hour sail away. Two very attractive anchorages, Still Pond and Fairlee Creek, are about 1 hour away. Rockall and the Magothy River are about two hours away. Baltimore, Annapolis and St. Michael’s are a one day sail. A cruise to the Soloman’s or to St Mary’s on the Potomac visiting the above places can be done in one week. There are excellent waterside restaurants on the Sassafras, Worton Creek, Fairlee Creek, the Chester R. in Chestertown, the Magothy River and the harbors at St. Michael’s, Annapolis, Baltimore and Rock Hall.

Bareboat charters and captained charters are available in the Virgin Islands too, click here for more information.

Click here for information on catamaran sailing charters or catamaran sailing lessons.