Embark on a guided adventure and discover the beauty of Chesapeake Bay. Sailing charters at Inn at Perry Cabin by Belmond combine luxury indulgence with unforgettable aquatic excitement.

Gliding elegantly through the waves, discovering the breathtaking nature of the Miles River, lulled by a gentle breeze—a chartered cruise is an unforgettable experience to share with family, friends or colleagues.

Each of our luxury yachts has a distinct personality and accommodates up to six passengers. Choose your favorite and let your captain take you on an adventure that you’ll treasure for years to come.

Star Bright, Star Light and Harbor Star


Five Star

Boating Concierge 
9am–6pm | 410-745-2200

Sailing Courses

Everyone can learn to sail at the Sailing Academy. Spend a laidback weekend learning the ropes, or throw yourself into an American Sailing Association certification course.

Choose your course


Enjoy indulgent accommodation as you learn to sail. Vacations at the Inn at Perry Cabin are made even more indulgent with our selection of sensational suites.

Find out more
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