St. Michaels Vacations

Historically known as "The Town that Fooled the British," St. Michaels, MD is the most popular destination in our collection of waterfront towns.  Offering a variety of activities, shops, and restaurants, there is something for everyone in the family to enjoy.  

Things to Do in St. Michaels, MarylandChesapeake Bay Maritime Museum

The Chesapeake Bay Maritime Museum is in the center of St. Michaels and offers visitors a  chance to learn about the heritage of the Chesapeake Bay.  The waterfront campus includes interactive exhibitions, tours, and scenic boat rides, demonstrations, hands-on education programs for children and adults, and annual festivals that celebrate the Chesapeake Bay culture.  

During the year, there are several fun events hosted by the Museum to enjoy--OysterFest in October, July 4 fireworks, the Charity Boat Auction, Big Band Night and Waterman's Appreciation Day are all local and guest favorites.

Kids love the opportunity to tour a real lighthouse, and the museum also offers family sleepovers for children to experience the life of a lighthouse keeper.

The Historic Mill Complex is an industrial hip-chic atmosphere and features a winery, brewery, and distillery. Spend some time tasting local wines, enjoying some spirits and learning about the beer making process.  
 
There is a fantastic array of restaurants in St. Michaels, and you are in for a treat as you stroll along the charming town.  st michaels vacation crab claw restaurantFrom waterfront crab houses where you can learn to pick crabs and enjoy the best local seafood while taking in bay breezes and scenic water views, to upscale restaurants with fine dining for a special evening out, you will want to bring your appetite along.  Some of our favorites include Limoncello, for authentic Italian cuisine, Ava's for delicious wood-fired pizza, Theo's Steak House, and St. Michaels Crab & Steak.  The Crab Claw is a local icon offering an authentic crab house experience overlooking the harbor.  For a sweet treat, Justine's is a local favorite for ice cream, and Gina's bakery serves up homemade goodies perfect to take home to enjoy along with your morning cup of coffee.

Want to get on the water?  There are many opportunities to take in a boat ride or charter, or for the more active vacationer, you can rent kayaks or paddleboards.  A guest favorite is the H.M. Krentz, a working skipjack offering daily tours to learn about oyster dredging and local history and experience the life of a waterman by helping pull up sails.  The Patriot offers narrated cruises aboard a replica of a 1930's steam ferry, or for an upscale sailing experience, the Selina II is perfect for an intimate sunset cruise.  Shore Pedal and Paddle has an array of kayaks and paddle boards for you take out or stop by the Maritime Museum to rent a boat there.

Biking is very popular in St. Michaels whether you'd like to just explore the town at a slow pace or take on a more ambitious ride along some of our scenic bicycle trails.  Several shops offer bike rentals for all ages and levels of experience. 

The historic district of St. Michaels is also home to some of the best shopping around!  You can find a keepsake treasure in the local antique shops, browse the many upscale boutiques, discover a new favorite artist in one of the eclectic art galleries or get some inspiration for your home by visiting some of the furniture and accessories shops.  Kids love the candy and Christmas shops, as well as the souvenir stores (crab hats, anyone?) to find that perfect keepsake for your visit. 

An offseason trip to St. Michaels will not disappoint.  Starting in October, St. Michaels hosts a variety of fall events where you can enjoy the cooler temperatures, beautiful foliage and seasonal delicacies such as oysters and crab soup.  Fall into St. Michaels weekend in October is a family-friendly event or be sure to visit for Oysterfest for great seafood, music, and local flavor. 

St. Michaels is one of the best Christmas destinations on the East Coast. The town pulls out all of the stops with spectacular holiday decorations, parades, homes tours and more.  
 
Eastern Shore Vacation Rentals is proud to offer a variety of St. Michaels Vacation Rentals for your next visit.  Browse and book these beautiful properties today!