The Eastern Shore of Chesapeake Bay
The Eastern Shore of Maryland is known for its beautiful harbors, stately homes with lush green lawns reaching down to water's edge, and delicious fresh seafood. Steeped in rich colonial history, prestigious Talbot County where our Chesapeake Bay sailing school is located, boasts the most shoreline in the continental United States and is considered one of the premier destinations in the Mid-Atlantic Region.
Where sailors love to sail
The location for sailing is outstanding. Here is where sea captains long ago retreated to protected coves and racing sailors today head out for friendly competition on our continent's largest estuary. With a watershed extending from New York to North Carolina, and Appalacia to the Atlantic, this is the cradle of life where salt and fresh water mix. Read Scott Nugent's story about the St. Michaels Learn to Sail gift his wife gave him here.
Upscale, elegant, old-world and fun
St. Michaels, Maryland on the Eastern Shore has a magical charm, with immaculately kept colonial, 
federal and Victorian homes and handsome churches. Many of these homes are summer retreats for sailors. On St. Michaels' main street you'll find small town charm with homes converted to delightful restaurants and shops. Lining the harbor are wonderful seafood eateries from very casual to candelight dining, where you can enjoy breakfast, lunch and dinner in the open air and watch boats come and go.
"St. Michaels was a gorgeous faciliy for learning to sail. Our instructor, Dave Manheimer, was absolutely terrific. He was so knowledgeable and patient - he made sure you understood every aspect of sailing the Colgate 26. We highly recommend this course and location to anyone interested in learning to sail. Outstanding experience!
Diane V. Gensler – Holtland, PA
Glorious views in an artistic retreat
This is an upscale peaceful place bathed by glorious views. The renowned Maritime Museum is a short walk from our Chesapeake Bay sailing school and the heart of town. All manner of artisitc talent blooms among scenes of steamboats, century-old log canoes, and every other type of water craft you can imagine. A short drive from St. Michaels are more towns with old-world charm and impressive vistas.
Here's where you can Learn to Sail in elegance, at The Inn at Perry Cabin on the Miles River, a 54 mile tidal waterway which flows into the Eastern Bay of the Chesapeake. The river itself produces an abundance of blue crab, oysters and succulent fish.
Three days or a week with Steve and Doris Colgate's Offshore Sailing School at The Inn at Perry Cabin on the Eastern Shore of the Chesapeake is a very special experience.
Click here to learn more about your Chesapeake Bay sailing vacation or call 888-454-7015 to talk to a friendly sailing advisor.