The Chesapeake is Calling

The Chesapeake is Calling

What Should You Explore? We'll Help You Decide

Once you make a reservation, our Guest Services will help you get to know the area and plan your stay. By the time you arrive, everything you want to do at the Inn, in St. Michaels and beyond will be scheduled and ready for you to enjoy.

Arrive By Hinckley

Begin your vacation before you leave the mainland. The Five Star, Hinckley Talaria 55, will pick you up in Annapolis for a luxurious butler-serviced voyage to the Inn.

Experience Sailing

There's nothing like the moment when a sailboat heels over, rail in the water, and sprints across the bay. We have three beautiful daysailers waiting to take you out. Group sails leave throughout the day, or you can arrange a private tour complete with lunch, sunset cocktails and dinner and a full bar.

Motor the Bay

Explore for a few hours with a group tour, or charter a private voyage. Our motor yachts, The Five Star and the Harbor Star can explore the river or take you far into the Chesapeake bay. A choice of catered meals and a full bar makes for a perfect journey.

The Sailing Academy

Whether you're a landlubber with a few hours to spend, or a skilled sailor looking to push your limits, our certified sailing instructors offer everything from the basics through multi-day sailing certification courses.

Hit The Links

Designed by the legendary Pete Dye, Links at Perry Cabin is a work of art that tees up a truly world class golf experience that will challenge golfers at every level.

Learn More About The Links

Get Some Court Time

Schedule a tennis match on one of our 3 Har-Tru courts or sign up for a lesson with our Cliff Drysdale Tennis Pro. Our courts are lighted and are open for seasonal play starting on April 15th.

To reserve court time or a lesson, Please call 443.258.2228.

Pedal into Town

Explore St. Michaels and the surrounding area by bicycle. The flat Maryland Shore roads with the magnificently wide shoulders make biking a pleasure. A short half-mile ride will take you to the charming center of St. Michaels where you'll find wonderful museums, quaint shops, and galleries.

Explore the Waterfront

Grab a paddle board or a sea kayak from our docks and chart your own adventure. You can paddle near the Inn or make your way over to St. Michaels for a picturesque view from the water. Instructions and classes are also available.

yoga at sunrise on the lawn

Immerse Yourself in Wellness

Join us for yoga on the Miles River, Qi Gong in the garden or take a spin class on a Peloton bike in our state of the art facility. Our fitness and wellness classes are available every day of the week.

Roam the Gardens

The Inn is built on 26 acres of gardens, orchards, wildflowers and lawns that our guests love to wander. Schedule a tour with our horticulturist to learn about gardening and see how she creates beauty for every corner of the Inn, from our hydrangeas to the flowers in your room and the herbs that flavor your meals.

croquet mallet

Lawn Games

Let the weight lift off your shoulders, relax and enjoy our beautiful Croquet Lawn and Bocce Courts. Some friends, a cool drink or a shot of espresso, and a good whack of the mallet will do wonders for your state of mind!

colonial painting next to stairs

Colonial to Contemporary

Take a step back in time to learn about the core culture of the Eastern Shore and Inn at Perry Cabin’s place in history. Learn the truths behind our storied past and find out why St. Michaels has been known as “the town that fooled the British” through one of our history tours and lectures.