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Nautical Adventures

 Offshore Sailing School  

Sailing School
The Inn at Perry Cabin is home to the Chesapeake Bay’s Offshore Sailing School, the perfect setting for a sailing school vacation. Choose from the signature three-day Learn to Sail course, or relax and learn in half-day sessions over five-days. If you already have the basics down, take the five day Bareboat Cruising course.

Courses are available any time April through November at The Inn at Perry Cabin. Contact the Offshore Sailing School for further information at sail@OffshoreSailing.com.
 
 Harbor  

Patriot Cruises
The Patriot leaves from The Crab Claw restaurant, within walking distance of The Inn. Learn about the history of Talbot County, view historic homes, waterfowl and the watermen who harvest the blue crabs, clams and oysters. The boat is a double-decker, with an open top deck and glass enclosed main deck. Cruises run daily at 11:00am, 12:30pm, 2:30pm and 4:00pm and charters available for special events.

For schedule and reservations contactinfo@patriotcruises.com.

 
 Pier  

Fishing
Captain Don Conley of "Let it Ride" boat tours has entertained visitors to St. Michaels and The Inn at Perry Cabin for over 10 years. Relax in style as you fish for rockfish, striped bass and more aboard a custom-built charter boat along the Chesapeake Bay. The boat is fully equipped and ready to bring home the big ones.

To book your fishing trip, please contact Let it Ride at dconley@bluecrab.org.

 
 Shipjack Excursion  

HM Krentz
The H.M. Krentz is an authentic working skipjack and one of the newer vessels to be built for the rigors of Maryland's wintertime commercial oyster dredging fishery. To sail aboard the H.M. Krentz is akin to stepping back in history, which is ever present on the Eastern Shore - home of the last fleet of working sailing vessels in North America.  The 32 passenger shipjack is available by charter to groups at reasonable hourly rates, or individuals can join scheduled two hour tours.

For schedule and reservations contact hmkrentz@bluecrab.org.

 
 Sailboat Sun  

Selina II
The Selina II is an antique, restored catboat that leaves from St. Michaels Harbour Inn. Tours are approximately 2 hours. The cost is $50 per person for day sails, $65 per person for sunset sails Sunday - Friday and $75 per person for Saturday sunset sails. Sunset cruises leave at 5:30 pm and return at approximately 7:30 pm. The Selina II holds six people.

For schedule and reservations contact sailselina@aol.com

 

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 »