For boaters exploring the Chesapeake Bay, St. Michaels, Maryland, is a must-visit destination. This charming waterfront town offers rich maritime history, fantastic dining, and a welcoming boating community—all set against the backdrop of the scenic Miles River. St. Michaels has excellent options for transient boaters, including St. Michaels Marina, Harbour Inn Marina, and the Chesapeake Bay Maritime Museum Marina, all providing slips with easy access to town. If you prefer to anchor, the Miles River and San Domingo Creek offer protected spots with dinghy access.
Once ashore, there’s plenty to explore. A visit to the Chesapeake Bay Maritime Museum is a must, offering interactive exhibits, historic boats, and beautiful waterfront views. Food lovers will enjoy indulging in fresh seafood at The Crab Claw, dockside bites with a view at Foxy’s Harbor Grille, or a gourmet meal at Limoncello. For those who enjoy craft beverages, St. Michaels Winery, Lyon Rum Distillery, and Eastern Shore Brewing provide tastings of locally made wines, spirits, and beers. A stroll down Talbot Street reveals boutique shops, art galleries, and specialty stores, while bike rentals offer a fun way to explore the town and its scenic waterfront.
The best times to visit St. Michaels are spring and fall when the weather is mild and the crowds are smaller, but summer is lively with events like the Watermen’s Appreciation Day and the St. Michaels Wine Festival. With its small-town charm, fantastic boating amenities, and rich history, St. Michaels is a perfect Chesapeake Bay getaway for any cruiser. Add it to your itinerary, you won’t be disappointed!
