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St. Michaels, Maryland on the Eastern Shore of Chesapeake Bay

The Inn at Perry Cabin is our Chesapeake Bay sailing school home. This Orient Express luxurious manor house resort and spa is located in the Victorian resort town of St. Michaels on the Eastern Shore of Maryland. A gift to a close aide of Admiral Perry, the land it sits on is absolutely beautiful with rolling lawns, meandering paths through lush gardens, and waterside views.

Learn in luxury

The Inn at Perry Cabin is an elegant colonial mansion nestled on the Miles River. Its grounds have been cultivated for almost 200 years. Maryland's oldest holly tree dating back to the early 1800's is located beside the front entrance to the resort and serves as the official Christmas tree of St. Michaels. 

The resort is "pet friendly" and considers your pet a member of its family. The entire staff thinks only of you, offering impeccable service.

Luxurious accommodations range from intimate garden view Signature rooms to Master Suites (shown here) with all the comforts of an elegant home. In addition to the usual amenities, all rooms feature plush robes, daily newspaper delivery, a fruit bowl and Milton Brown bath amenities. Flowers from the garden are placed in your room and throughout The Inn each day.

Premier resort spa 

The Inn at Perry Cabin's premier Linden Spa and Fitness Center offers a full range of work-out machines, fully-equipped private Yoga and Pilates studios. Named for the tall Linden trees lining the driveway to the resort, the Linden Spa uses Linden tree blooms and many other herbs from its gardens,  providing soothing services that focus on pampering, rejuvenation and wellness. A  beautiful heated horizon-edge swimming pool is centered in a richly landscaped brick-walled garden. Bicycles are complimentary. High speed internet access is available throughout. Fishing guides will pick you up at the resort, hunting and golf are nearby.

Award-winning culinary experience

Dining at The Inn at Perry Cabin is an unparalleled culinary experience. Sherwood's Landing, the only four-diamond restaurant on Maryland's Eastern Shore, overlooks the River and our sailboats. Here you can enjoy breakfast, lunch and dinner in a picturesque, yet relaxed setting, with award-winning Chef Mark Salter's unrivaled creations accented with regional specialities, fresh vegetables and herbs from The Inn's gardens. An outdoor terrace off the dining room is available for breakfast and lunch; tea and drinks are served wherever you like on the lawn as you relax and watch the world go by.

If you wish to savor a glass of vintage port, cocktails or enjoy selections from the a light-fare menu, Purser's Pub features a magnificent open-hearth fireplace and landscaped courtyard.

The perfect setting for a sailing vacation

Take our signature three-day Learn to Sail course any Friday-Sunday (arrive Thursday), or relax and learn in half-day sessions over five-days (arrive Sunday and depart Friday). If you know the basics, take our five-day Bareboat Cruising  course and arrive Sunday evening. If you want to get into cruising quickly, Offshore Sailing School provides the only comprehensive novice-to-ready-to-charter course you'll find. Fast Track to Cruising is an Offshore Sailing School exclusive –two full days on award-winning Colgate 26 sailboats, then five half-days on a beautiful 42' cruising boat.

"St. Michaels and The Inn at Perry Cabin campus is a superb location for couples who want to learn to sail together. The quality of the staff, instruction, and boats was first class in every way."
Randolph Young – Clifton, VA

Learn in total privacy

And all of these courses can be take as totally Private Courses for Two. Can you think of a more enticing place to Learn to Sail, take a Cruising course or get on the Fast Track to Cruising and go home with credentials to start sailing big boats on your own than this special retreat? We can't! Take a course with Offshore Sailing School any time April through November at The Inn at Perry Cabin on the Eastern Shore of Chesapeake Bay and find out why.

"If anyone is apprehensive about sailing or setting off on the water, they should take the Learn to Sail course from Offshore. My confidence grew every day and I felt so much at ease on the water as the week progressed. Our instructor was patient, knowledgeable and kind! We loved our week at St. Michaels both on and off the water!"
Pamela Young – Clifton, VA

The Inn at Perry Cabin
308 Watkings Lane
St. Michaels, Maryland 21663

Click here to get a quote on your very special sailing retreat or call 888-454-7015 to find out more. 

Courses offered