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 the Countryside

St. Michaels is just a few minutes away by bike. Beyond town lie miles of coast and gently rolling farmland to explore. You can grab a bike anytime you like, or ride an electric bike on one of our guided tours.

Explore On Your Own

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.

Build A Ship!

Well, part of ship, at least. Spend a day as an Apprentice Boat Builder at the Chesapeake Bay Maritime Museum in St. Michaels. You'll learn the basic tools, skills and techniques that go into building a wooden boat. Book early, the Apprenticeship is very popular.

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.

Catch Your Dinner

The Chesapeake Bay is the perfect place to cast a line or drop a pot. Whether you bring home a fish, some Maryland Blue Crabs or a bucket of oysters, our chefs will prepare your hard-earned catch to perfection.

Help Heal the Bay

Visit Phillips Wharf, the non-profit oyster farm that supplies our tables and produces oyster seedlings that are helping restore the bay. We promise an amazing experience and a tasty reward for your time.

Interested in Phillips Wharf? Just ask Guest Services to arrange a visit.