A Perfect Day in St. Michaels, Maryland

by Brian on August 16, 2013

in Guides, Tips

St. Michaels harbor

One of my favorite day trip destinations from Washington, DC is St. Michaels, Maryland. The town, located on the state’s beautiful Eastern Shore, is an easy 1.5 hour, 80 mile drive across the Chesapeake Bay Bridge from DC. It’s also relatively close to Baltimore and Philadelphia.

St. Michaels was founded in 1804 and has a rich history. It’s known as the town that fooled the British. Anticipating an attack during the War of 1812, the townspeople hung laterns in trees down river. This tricked the British into thinking the town was in a different location when they attacked early one morning, saving the town from significant bombing.

Today, St. Michaels is a quaint town of only 1,000 residents located on the Miles River, a tributary to the Chesapeake Bay. The town is full of old colonial homes, a picturesque main street, a marina, the Chesapeake Bay Maritime Museum, and numerous restaurant and hotel options.

Sailing the Miles River in St. Michaels

What to do:

No trip to St. Michaels would be complete without a trip out on the water. Several companies offer tours of varying lengths on different types of boats. The Patriot sails every hour from the marina and prices are $24.50 for adults, $22 for senior, children 12-17 are $12.50, and and children 3-11 are $5. The boat has two floors and a full bar. A trip on the Patriot lasts an hour and the captian provides a narrated tour of the sights along the Miles River around St. Michaels.

Patriot Cruise in St. Michaels

Other companies provide rides on smaller traditional sailboats. One company, Chesapeake Shipjack Sailing Tours, offers two-hour sailing excursions on the historic Shipjack H.M. Krentz for $35 per person.

After a sailing the Miles River, spend time wandering the streets of St. Michaels and check out the beautiful old colonial homes. The main street in town has many shops to explore offering goods ranging from touristy t-shirts to fine antiques and art.


St. Michaels has many good food offerings from casual to fine dining. My favorite places to eat are right on the water by the marina. Two options I recommend are Foxy’s Harbor Grill and the Crab Claw. Foxy’s is an outdoor tropical island-themed restuarant serving delicious crab cakes and St. Michaels Ale beer. It has a very low key vibe and is a perfect place to park for a few hours to enjoy some food and a couple of beers in the summer sun overlooking the water.

Across the marina is the Crab Claw. As the name suggests, this restaurant specializes in fresh Maryland whole crabs. The staff will set you up with newspaper on the table and a bucket of steamed crabs to crack open and enjoy with a cold beer. The place is great with a relaxed atmosphere right on the water.


If you’re looking for a weekend getaway to St. Michaels and feel like springing for a unique stay, the ideal option is the Inn at Perry Cabin. The hotel is located just outside the town center and sits right on the water. The original section of the property was built in 1816 as a small inn. In 1999, Orient Express purchased the property and expanded it to 80 rooms. Today, it’s a five star hotel with gorgeous water views, an outdoor pool, a luxury spa, and a fine dining restaurant. The hotel gained additional fame as the setting for the main wedding scene in the 2005 film Wedding Crashers. Room rates start at a pricey $350 per night. I stayed one night at the property in April 2012 and had an amazing time.

The Inn at Perry Cabin

TripBadger Recommendation:

If you’re looking for a quick weekend getaway from Washington, DC, Baltimore, or Philadelphia, St. Michaels should be at the top of your list. Definitely dine at Foxy’s or the Crab Claw, go for an afternoon sailing excursion, and consider a night at the Inn at Perry Cabin.

For more information, visit the St. Michaels tourism information website.


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