Boats and bistros on the Chesapeake.

Maryland’s Road Trip-Worthy Waterfront
Credit: Courtesy of Inn at Perry Cabin

Bask in the bay breezes of St. Michaels, Maryland’s most romantic harbor. Even the trip there, over long bridges connecting islands and peninsulas, is wistfully transporting.

Inn at Perry Cabin by Belmond

Set on the Miles River, a private Chesapeake Bay inlet, this hotel is chockablock with homey touches, like fresh-baked cookies at turndown. The Colonial-style 1816 manor's design concept was inspired by the Commodore's cabin on the U.S.S. Niagara and features nautical objects and Yankee antiques in the 19th century main structure, set on 25 lush manicured acres with a swimming pool centered in a brick walled garden. For seafarers, the hotel can arrange cruises and sailing lessons, while land adventurers will prefer complimentary bicycle rentals for exploring the Victorian streets and neighborhoods of St. Michaels, a chain-restaurant-free town steeped in rich colonial history and filled with antique shops. For dining, the inn’s Stars restaurant is well regarded as the best restaurant in this corner of the Eastern Shore. TheSpa at Perry Cabin, incorporates Linden blossoms in signature botanical treatments also sold in the apothecary.

Harris Cove Cottages Bed N Boat

Rent a motorboat to explore the Chesapeake’s open waters and hidden inlets.

Carpenter Street Saloon

Grab a beer and crab soup at this well-loved neighborhood joint.

Bistro St. Michaels

Dine on Chesapeake oysters or a duck magret at the Paris-inspired, dinner-only location.