Chesapeake Bay Sailing School, Sailing Instruction &

Learn to sail on the Chesapeake Bay or the British Virgin Islands. Upper Bay Sailing School provides world class sailing instruction and we have awards and references to prove it. We provide all our students, from beginners to advanced, with the adventure of learning to sail while on vacation in two of the most outstanding sailing areas in the world.

Upper Bay Sailing School is one of few sailing schools in the Chesapeake Bay and the British Virgin Islands to earn the Gold Standard Rating and we offer affordable lessons in two prime locations:

Sailing Classes - Spring, Summer and Fall

We are based in the Chesapeake Bay at Green Point Landing, Worton Creek, Eastern Shore Maryland. A beautifully situated, full service, deep water, owner operated marina ideally located for teaching and within 5 minutes motoring of open water sailing.

Sailing Classes - Winter, Spring and early Summer

Please note we have recently greatly expanded our program in the British Virgin Islands with an increased schedule, Advanced Classes and Catamaran Sailing Charters and Lessons.

From November through July, we have a base in the Caribbean Islands at Nanny Cay, Tortola, British Virgin Islands. Training boats are very well equipped cruiser/racers made by Beneteau. Go to NannyCay.com and click on the web cam for views of Nanny Cay Marina and Resort. Click on the other Nanny Cay thumbnails and you are in Paradise!

Upper Bay Sailing School, sailing lessons, Chesapeake Bay sailing school, British Virgin Islands

Sailing instruction at our Caribbean Sailing School in the BVI

Our Leopard 45 Cat
Available for sailing instruction and sailing charters.

Our Chesapeake Bay sailing base on Worton Creek

Info@UpperBaySailing.com