St Michael’s

St Michael’s
The delightful harbor of St Michael’s Maryland is worth visiting by land, or even better by sea. In the heart of the Chesapeake, on the Eastern Shore, arriving by boat in this serene seaside town is magical.

The highlight is the Chesapeake Bay Maritime Museum where you can join and dock your boat, or pay for a mooring. Be sure to tour the beautiful facility that’s preserving the history of the Chesapeake oyster fishing, boat building, lighthouses and more. If you are not sleeping aboard your yacht, The Inn at Perry Cabin is a posh waterfront resort with golf, tennis and a spa, and there are several quaint historic inns in town. Downtown St Michael’s’ Talbot Street is lined with great shops restaurants and the beautiful Saint Michael’s Church.

Top Things to do in St Michael’s

Chesapeake Bay Maritime Museum is a sprawling waterfront campus with exhibits of boat building, oyster fishing, crab shucking, and preservation efforts to the world’s largest estuary – the Bay itself. Its kid and nerd friendly with so many fun and fascinating facts.

Hooper Strait Light is now at the Chesapeake Bay Maritime Museum in Saint Michaels, go to the top of this unique hexagonal light to see the spectacular Fresnel Lens and admire the rugged lifestyle of the lighthouse keepers on this screw pile light specifically designed for the shallow waters of the Chesapeake.

Stroll Talbot Street’s antique stores and trendy boutiques too, like the Preppy Redneck, home furnishing places, wood carving galleries and more.

Tour St Michael’s classic car museum for a a step back in time on the road. Antique autos and motorhead memorabilia fill this barn.

Drink up at St Michael’s Distillery – featuring rum. Also Eastern Shore Brewing has a fun brewery on Talbot offering tastings of their micro beers. St Michael’s Winery and Great Shoal Cellars Winery both offer flights and tastings as well as their wines for sale in a fun not-so-fancy oenophile atmosphere.

Breakfast at Carpenters Street Saloon is a throw back, serving traditional diner fare, filling homemade omelets, hash browns, pancakes, in an old pub atmosphere – corner of Talbot and Carpenter.

Lunch at Limoncellos – a sophisticated Italian inspired café on Talbot, look for the cheery yellow signage and décor.

Walk St Michaels’ historic streets and admire the beautiful architecture of the homes from the 1700 and 1800’s here. The gentile wrap around porches and detailed woodwork is amazing, as are the gardens and landscaping on each quiet shaded street.

Foxy’s on the harbor has a fun tropical vibe, like a beach bar on the docks overlooking St Michael’s Harbour Marina. Foxy’s is fun for happy hour with $4 drinks, often with live music, plus seafood – crab or rock fish and tropical cocktails at lunch and dinner.

Theo’s is great for steak dinner at this casually elegant steak house – delicious burgers, steaks, meatloaf, plus the bourbon shrimp appetizer. Theo’s bar is very popular with locals, always a good indicator. Theo’s has happy hour midweek too with drink deals and app specials.

208 Talbot is the best restaurants for special occasion dining. The Crab Fried Rice entree is extraordinary, and plentiful. The Rockfish stuffed with crab is also delicious. The atmosphere is old world elegant overlooking Talbot, the bar is cozy too.

Stay at the Inn at Perry Cabin for sublime resort luxury overlooking the harbor, with golf, a spa, pool, tennis and marina. This exclusive resort property caters to an upscale clientele with its peaceful setting on a point in the Bay. Guests enjoy superb service on quiet well-manicure grounds not far from downtown St Michaels.

St Michael’s is a short car ride, or a few hours sail, across the Bay to Annapolis, or Tilghman Island – another cool Chesapeake town, and Oxford. There is even a bike loop from St Michael’s to Bellevue, where you catch the Oxford Bellevue Ferry to Oxford.

More on Cruising Chesapeake Bay

Solomons Island 
Tilghman Island

More Charter and Cruising Reviews

“The best trips answer are questions that you never asked before”