If you’re interesting in charting a sailboat on the Chesapeake Bay or beyond, click through the buttons on this page for sailing resources, such as destination and how-to articles, tips for sailors on provisioning and planning, and charter company ideas.

Were I offered a chance to charter in a place I had been to before, hands-down I would pick Guadeloupe. More specifically, I’d choose to spend my days exploring Les Saintes and Marie-...
We had sailed to Bequia in the Grenadines, a chain of islands in the Windward Isles that group together as one country under St. Vincent.
Onboard entertainment for sailing charter vacations or even an evening at anchor near home. ~ By Zuzana Prochazka
Most sailing trips in Mallorca start in Palma, as did ours. The ancient, south-facing port city has an amazing medieval quarter.
Even when you live in the Land of Pleasant Living as we on the Chesapeake do, you might crave a mid-summer charter escape.
Longtime friends continue their decades-old "boys sails" tradition with an early 2023 sailing charter in the BVI.
In the wake of Hurricane Dorian in 2019, the Abacos, Bahamas, are still in recovery mode yet sill have a lot to offer charter sailors. ~By Eva Hill
For sailors who find the winter months a bit dull, the Caribbean offers a wide range of great regattas, and one of my favorites is Grenada Sailing Week.
Find an authentic Caribbean experience while taking a charter sailing vacation in Antigua and Barbuda.