Break out your best nautical garb for the return of the fleet at The Inn at Perry Cabin.
Kick off the sailing season with the return of the Inn’s fleet of sailboats as they cruise through the Chesapeake Bay waters back to the resort’s marina.
Nestled on 26 acres overlooking the picturesque Miles River on Maryland’s Eastern Shore sits The Inn at Perry Cabin, a boutique luxury retreat inspired by the region’s rich nautical heritage. Originally a War of 1812-era farm, this gem of a resort combines casual luxury grounded in historical colonial charm with an escape to the Chesapeake Bay area, just a few hours south of Philadelphia.
The 26-acre St. Michaels property houses 30 suites and 48 guest rooms and was designed by renowned designer Alexandra Champalimaud. The original architectural details mingle classic style with modern comfort perfectly. French doors lead to private decks, patios and verandas, and the rooms feature waterfront or lush garden views, modern furnishings and nautically inspired interiors. The ambiance is so quaint and idyllic that it even served as the perfect location to shoot 2005’s Wedding Crashers.
The Inn’s storybook setting offers guests a nautical-themed respite on the banks of St. Michaels’ Miles River.
The Inn’s acclaimed STARS restaurant showcases the culinary wonders of the Chesapeake Bay, offering a menu that changes seasonally to highlight fresh produce, locally sourced meats and the day’s catch straight from the Bay. The Inn’s culinary team has close relationships with local farmers and fishermen, ensuring that their ingredients are ethically and sustainably sourced—they follow a nose-to-tail approach, using every part of the animal or fish to minimize waste and promote a sustainable food cycle. And for an even more exclusive dining experience, guests can dine in one of four private options known as “The House.” Located in various settings around the property, these venues create perfectly intimate spaces to dine or celebrate.
With a pristine fleet of sailboats, the Inn boasts one of the region’s most celebrated sailing programs.
The rest and relaxation don’t end with the dining. Golfers can play the Links at Perry Cabin, a Pete and Alice Dye-designed 18-hole course with stunning views of the Eastern Shore. The Inn also features eight golf simulators and a Cliff Drysdale tennis program with clay courts and lessons. Spa lovers can book a treatment at the Spa at Perry Cabin for therapeutic bodywork that uses plant-based treatments made from herbs and aromatics grown in the Inn’s own garden and harvested from farms throughout the Eastern Shore. You can even go off-property and enjoy activities around St. Michaels (est. mid-1600s) by hopping on one of the Inn’s complimentary bikes to explore the charming town and the local galleries, boutiques, Maritime Museum, local winery and Lyon’s Distilling Company for rum tastings.
The historic property originally began as a farm after the War of 1812.
But for sailors, yachties and just about anyone who loves watching gorgeous vessels on the water, the Inn’s annual Return of the Fleet (April 10-12) is a weekend to be treasured—and reserved. After a long winter, the Inn’s pristine fleet of sailboats and Alerion yachts—including a 55’ Hinkley and the latest addition, a 1902 skipjack Stanley Norman that famed American writer James Michener sailed on researching his bestselling novel Chesapeake—returns in grand style to the Inn’s docks on the Miles River. This lively event offers guests the chance to admire the boats and enjoy a variety of waterfront activities, including sailing, kayaking and paddleboarding. But even if you can’t make it for Return of the Fleet weekend, the Inn boasts one of the region’s most celebrated programs, offering sailing adventures on its sailboats and yachts—all captained by Inn staff—throughout the end of the summer.
Photography by: BY THE INN AT PERRY CABIN
