Learn the best things to do in St. Michael’s, Maryland for a day trip or a relaxing weekend. We visited for a romantic long weekend getaway and are excited to share our top picks based on our experiences. You’ll walk away with the best activities, shops, restaurants, hotels, and helpful tips we learned along the way. Let’s plan your trip to St. Michael’s!
About St. Michael’s, Maryland
St. Michaels, Maryland, is a picturesque town known for its historic charm and maritime heritage. Set on the eastern shore of the Chesapeake Bay about 27 miles from Annapolis, it offers 19th-century architecture and scenic waterfront views.
Spend a day in St. Michaels by exploring historic sites, enjoying waterfront views, visiting the Chesapeake Bay Maritime Museum, and/or strolling through boutique shops and antique stores. Dine on local seafood, especially crab, and take a scenic boat tour.
This small town is worth visiting for a short and relaxing getaway of one to three days. It’s also extremely walkable, bikeable, and driveable. It feels like a mid-Atlantic version of Chatham in Cape Cod or Edgartown in Martha’s Vineyard.
The best time to visit St. Michael’s, Maryland, is during summer, as events and water activities are at their peak. Visit in spring and fall for mild weather, fewer crowds, and beautiful scenery, but note that it may be too cold for water activities.
Best Things to Do in St. Michael’s, Maryland on a Weekend Getaway or Day Trip
Top Local Restaurants and What to Order
I did some research ahead of time and talked to locals and acquaintances who visited St. Michael’s restaurants, and I was SO pleased with our dining experiences. I would go back to any of these restaurants in a heartbeat!
This is the trendy, new hot spot for new American fine dining, located in The Wildset hotel, right on the main street (pictured above). First, dinner service was exceptional — to the point where my husband reached out afterward to thank them. They were very well-staffed, and we were never without attention and full glasses. The food was excellent too!
This charming French bistro on the main street (pictured above) was so cozy and romantic, and the staff was very helpful and friendly. We got a bottle of Bordeaux for a reasonable price, and the food was excellent. The pasta was my favorite pasta dish in a long time, and my husband said his steak was very well prepared.
We ate brunch at the Inn at Perry Cabin‘s on-site restaurant, and again, everything was excellent. The upscale ambiance and stunning waterfront views cannot be beaten, either.
We wanted to grab lunch at a casual local seafood spot, and Captain Iris on our Sail Selina II boat tour recommended this waterfront establishment, right on the marina. I was impressed by their Caribbean vibes, vegetarian options, and large menu of “crushes” to drink.
ON MY LIST FOR NEXT TIME:
You can never do it all! I heard good things about these places too:
- Justine’s for ice cream
- The Crab Claw for casual local seafood and a waterfront view
- Ava’s for homemade pizza and pasta
- Eastern Shore Brewing
- Lyon Distilling for rum
- St. Michael’s Winery
Hotels: The Inn at Perry Cabin and Beyond
Inn at Perry Cabin
The Inn at Perry Cabin is a historic colonial mansion and luxury resort on Maryland’s Eastern Shore, offering picturesque views of the Chesapeake Bay and traditional American decor. It’s within a very short walking distance of the town center of charming St. Michael’s.
It’s famous for being the location where the upscale wedding in the movie Wedding Crashers was filmed. Like the movie, it gives very elite Washington, D.C. vibes.
WATCH MY 30 SECOND VLOG
MY FAVORITE RESORT AMENITIES
- Fine dining with an unbeatable view
- Spa and outdoor pool with a bar
- Beautifully manicured gardens
- Activities like tennis, bocce ball, and fire pits with smores
- On-site daily activities (like glass etching and yoga)
- Golf
- Bicycles
- Fleet of boats for excursions
- Extremely dog friendly
my favorite Room amenities
- Very large “deluxe room” with a seating area, a balcony with a view, and even a gas fireplace
- Very large bathroom with double sinks, closet, and separate shower, bath, and toilet
- Clean and tidy; prompt maid service
- Nespresso machine and free water bottles
- Turn down service with yummy sweet treats at night
MORE OF THE INN AT PERRY CABIN
We rate our stay at the Inn at Perry Cabin in a “deluxe room” five stars.
PROS:
The luxurious Inn at Perry Cabin was everything we wanted in an upscale, romantic weekend getaway, and we do intend to return. The accommodations, amenities, attention to detail, and overall service are all top-notch.
The waterfront location is both stunning and so close to town.
Ultimately, you get what you pay for! It’s among the top few places we’ve stayed.
CONS:
I wished there were more food options. There is one restaurant (Stars) and one small bar (Purser’s Pub) and, while the food at both was delicious, the restaurant offers just one tasting menu for dinner, and we found the room service options to be limited. We also thought the food at the High Tide Pool Bar was “just okay” for the high-end price tags.
Lastly, while there is a gift shop, it also lacked basic sundries we forgot, such as sunscreen and bug spray, which we bought in town.
PACKING TIPS:
Pack for seasonal waterfront weather. Note that the style is very preppy and upscale (think: more like business casual than tourist casual). My Lilly Pulitzer dresses fit in well. My husband wore Vineyard Vines. Golf wear is also appropriate.
Another St. Michael’s Hotel to Consider
Recap
The best things to do in St. Michael’s, Maryland, offer small-town charm with a maritime twist! I recommend a mix of relaxation and activities over one to three days. My top picks are:
- Hotel: Inn at Perry Cabin
- Restaurant: Bistro St. Michael’s
- Activity: Sail Selina II
