Located along Chesapeake Bay, the inn dates back to the 17th century. It barely survived a British attack during the War of 1812.
The property has four guesthouses, each built in a different era and surrounded by shade trees with hammocks. You’ll enjoy breakfast in the Georgian-style main house, built in 1819.
Each room has its own personality—some come with four-poster beds, others are accented with antique rocking chairs and quilted bedspreads. All of the included rooms have views of the bay.
Breakfast typically includes fresh-baked muffins and rolls, fruit, orange juice, and coffee. It’s served in wicker chairs in the dining room of the main house, which overlooks the bay. The eggs, milk, and meat served all come from local farms.
You can rent one of the inn’s bikes and explore the coast or hop on a kayak to explore the bay. If you cast a line right from the shore, you might catch some rockfish or bluefish.
It’s not unusual to see owls, blue herons, and bald eagles on the property. There’s a list of “must-see birds” on the fridge in the main house.
St. Michaels, Maryland: Seaside Views and Maryland Blue Crabs
In addition to exuding seaside charm, the sleepy town of St. Michaels is notable for having played a starring role in a little-known episode in American history—its residents outsmarted the British during the War of 1812. The townspeople reportedly hung lanterns in trees outside of town to trick the Brits into thinking they were dramatically misfiring their cannons. The redcoats overshot and the town survived.
While you’re here, be sure to partake in the area’s rich maritime culture. Watch the ships gliding by on the Chesapeake Bay and try some of Maryland’s famous blue crabs. For an in-depth look at the town’s history, visit the Chesapeake Bay Maritime Museum or take an educational sailing tour on the H.M. Krentz skipjack, which departs right from the museum.