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Offshore Sailing School

The Inn at Perry Cabin is the Chesapeake Bay home of the Offshore Sailing School, and the perfect setting for a sailing school vacation.

Let the adventure begin by scheduling a class during your next stay at The Inn. Sailing courses are offered in a variety of lengths to accommodate guests at every skill level. It's a great way to experience the Chesapeake Bay in all her glory.

Choose from the 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 already have the basics down pat, take the five-day Bareboat Cruising course and arrive Sunday evening.

If you want to get into cruising quickly, Offshore Sailing School has the only comprehensive novice to ready-to-charter course you'll find. Fast Track to Cruising is an Offshore Sailing School exclusive with two full days on their award-winning Colgate 26 sailboats, then five half-days on a beautiful 43'-49' cruising boat.

Don’t want to learn in a group? Each sailing course is available as totally private courses for two.

Discover adventure with the Offshore Sailing School courses any time April through November at The Inn at Perry Cabin.

Contact the Offshore Sailing School for further information, quotations and to book. Tel: 888-454-7015.

   Sailing
 

Features & Offers

Winter Indulgence Package

Winter Indulgence Package

Join us along the Chesapeake's Miles River for award-winning fare, signature spa treatments and classic cocktails. More »
Weddings

Weddings

The Inn at Perry Cabin makes for an impressive and unique location for a destination wedding. More »
Advanced Purchase

Advanced Purchase

Book early and save up to 10% off our Best Available Rate. Rates from $248.00. More »
Shopper

Shopper's Paradise

Just a short walk from The Inn, St. Michaels is full of antique shops offering a very good to fine quality range of finds. More »
Gift Certificates

Gift Certificates

Our gift certificates can be used for a stay, spa treatment, lunch or dinner, afternoon tea or drinks. More »
Nautical Adventures

Nautical Adventures

Experience Maryland’s famed Eastern Shore firsthand.  More »