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Photos by Dori Arrington

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If you were to dream of the world’s most beautiful seaside villages to visit by boat, picturesque destinations like Positano, Italy; St. George’s, Bermuda; or maybe Lunenburg, Nova Scotia would come to mind. Fortunately for boaters on the U.S. Eastern Seaboard, you don’t have to go that far to appreciate this world-class scenery. One such quintessential harbor is nestled on a well-protected cove on Maryland’s Eastern Shore.

Founded as a deep-water port in the mid-17th century, St. Michaels’ existence is inextricably intertwined with the sea. Originally established for loading Eastern Shore tobacco on ships bound for Europe, it gained international acclaim as a safe, welcoming harbor. The boats arriving today may look different, but they are just as welcome and just as important to St. Michaels’ vitality.

Over the warm Chesapeake summer months, St. Michaels plays host to large numbers of visiting boats from Annapolis, Baltimore, Washington and Philadelphia, and the town is laid out perfectly to accommodate them, with marinas lining the waterfront.

Beginning in the south is the St. Michaels Harbor Inn Marina and Spa, a beautifully maintained facility on the quiet side of the harbor. Located in the center of town is the St. Michaels Marina, a family-run business now operated under the watchful eye of the founder’s son, Michael Morgan. Surrounded by restaurants and only steps from downtown, St. Michaels Marina is the preeminent location for visiting yachts, welcoming all boats from small cruisers to 200-footers. Next is Higgins Yacht Yard, the only working yard in town.

If the quiet of a protected anchorage is more to your liking, the Miles River provides secure holding and enough space to accommodate the largest of yachts without feeling crowded. A floating dinghy dock is located in the center of town, and there is a water taxi to provide shuttle service.

Regardless of where the boats moor, you can find boaters and townsfolk mingling over a beverage at Foxy’s Harbor Grille, a Caribbean-themed beach bar and restaurant on the waterfront adjacent to the marinas.

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In addition to its importance as a port, the Eastern Shore’s dense forests and deep water made St. Michaels a natural location for ship building. For many years, the sleek schooners built in St. Michaels and the surrounding towns of the Chesapeake Bay were some of the fastest sailing ships on the oceans. Eventually gaining fame as Baltimore Clippers, these schooners were the pride of the colonies.

Today, that ship building history is being preserved at the Chesapeake Bay Maritime Museum. Located on 18 waterfront acres in the heart of town, it is one of the country’s premier maritime museums. With an impressive fleet of restored craft, the museum tells the story of the Chesapeake Bay through the eyes of the watermen that worked it. The museum also has slips available for members.

As important as ship building was to St. Michaels, it is the Bay’s abundant stock of crabs and oysters that punctuates the town’s character today. While the main waterfront is less of a working harbor than it once was, it only takes a short walk to St. Michaels “back door” on San Domingo creek, where crabs are loaded onto trucks for market daily during the season.

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Through efforts in sustainable aquaculture, the Chesapeake Bay’s prized oysters are making a comeback in St. Michaels. Oyster farming operations like Ferry Cove Shellfish and the St. Michaels Oyster Company are thriving. These innovative businesses supply the restaurants in the area with high-quality local seafood while simultaneously contributing to the local economy and the health of the bay’s water quality. In past years, the Maritime Museum had to import an increasing number of oysters for its popular Oyster Festival held every October. Today, they celebrate with delicious, locally farmed and grown bivalves. Beyond enjoying some of the Chesapeake’s best steamed crabs, crab cakes and fresh rockfish, you won’t go thirsty in St. Michaels either. Local entrepreneurs converted some of the old packing houses and industrial buildings into an award-winning winery, distillery and brewery.

If you can’t get there by boat, don’t worry. St. Michaels has boutique hotels, quaint inns and the renowned four-star Inn at Perry Cabin, which is situated on 26 acres of waterfront, adjacent to the Maritime Museum. The resort combines a casual Eastern Shore laid-back luxury with the elegance of a fine estate.

Three hundred and fifty years of seasoning in a crab and oyster chowder has made St. Michaels one of the Chesapeake Bay’s greatest treasures.

This article originally appeared in the May 2022 issue of Power & Motoryacht magazine.

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