The Chesapeake is Calling

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.

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.

The Inn is built on 26 acres of gardens, orchards, wildflowers and lawns that our guests love to wander. Take a stroll through our lush gardens and discover the beauty our onsite horticulturist has created for every corner of the Inn, from our hydrangeas to the flowers in your room and the herbs that flavor your meals.

Join us for an educational voyage aboard the latest addition to our Fleet! This 1902 oystering Skipjack boasts an illustrious history and impressive longevity as one of the remaining 35 in operation from the thousands that once dredged the Chesapeake Bay. Visit here for more information. 

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. Additional information may be found here.

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. Explore more here.

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. For more information please call 443.258.2228.

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. Explore more here.

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

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 open for seasonal play starting in April through October, weather permitting.

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

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.

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!

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.