St. Michaels, Maryland

Set beside the historic Chesapeake Bay, St. Michaels, Maryland, is a charming seaside town with a laid-back coastal feel and plenty of history to explore. Stay with Inspirato at Mulberry, an expansive, six-bedroom home steps from Grace Creek with its own private dock. Enjoy ample outdoor space, including a pool, outdoor kitchen, and fire pit.

Destination Highlights

Sail On an Oystercatcher

The Inn is known for its sailing academy and many guests even arrive by boat. You can sail on the HM Krentz skipjack boat, one of the last operational oystercatchers in the U.S.

Chesapeake Bay Maritime Museum

This interactive museum houses the world's largest collection of Chesapeake Bay boats, and its waterfront campus is one of the most famous working shipyards in the country.

Farmers Market

On Saturdays from April through October, peruse fresh produce and local wares within the St. Michaels Farmers Market. As you shop for goods, you’ll be treated to live music performances.

About St. Michaels, Maryland

Coastal Small Town Living

Nestled along its picturesque namesake harbor, St. Michaels offers historic charm—there’s a reason it’s nicknamed the Heart and Soul of Chesapeake Bay. Settlers flocked there from the 17th century on to build ships and grow tobacco. Today, St. Michaels is coastal Americana at its finest, with laid-back days best spent on the water. As you wander St. Michaels’ charming harborfront streets, you’ll feel as if you’ve slipped back to the 18th century, with noteworthy bay vessels and skipjacks dotting the coastline and woodlands extending across the region. It’s also an easy weekend getaway from Washington, D.C., Baltimore, or Philadelphia.

Forecasting Your St. Michaels Vacation

Summers in this East Coast town are very warm and humid, with occasional rain showers and temperatures averaging in the high 80s, ideal for getting out on the water. Winters are very cold and windy—the best time to visit St. Michaels is usually from Memorial Day to early October.