Inspiring Artists, Architects, And Adventurers Since 1677.

St. Michaels is a special place. The sense of history and charm you feel here is authentic, established over centuries. Since the late 1600s when it served as a trading post for Eastern Shore farmers and trappers, through the 1800s when it was a shipbuilding town, St. Michaels has always attracted free spirits with a love of water. Today, this maritime village is the heart and soul of the Chesapeake, a wonderful place to visit, and an even better place to live.


Named A “Top 10 Coastal Town in America.”

In 2015, the USA Today Readers’ Choice Awards recognized St. Michaels as being among the very best coastal towns in the country.

St. Michaels is a small town with a world-class setting, flanked to the east by the Miles River and to the west by Broad Creek and San Domingo Creek. Everyone here feels a connection to the water, though how you decide to enjoy it is entirely up to you. Whether you are a boat-owning, Chesapeake-loving Sea Dog at heart, or simply want a more relaxed lifestyle with long walks along the shore, you’ll feel an instant bond with St. Michaels. Iconic waterfront attractions, like the Hooper Strait Lighthouse at the Chesapeake Bay Maritime Museum and the famous Inn at Perry Cabin, along with an eclectic mix of boutiques, galleries, and restaurants, are all just an easy walk or bike ride away from San Domingo Cove.


Your path into town.

At the entrance to San Domingo Cove, you’ll find the St. Michaels Nature Trail, a 1. 3 mile path that winds along woods and water, and connects to downtown St. Michaels. It’s wide, it’s paved, and it’s sure to be your new favorite way to bike into town, enjoy a morning walk, or jog off last night’s ribeye from Theo’s.


5-star neighbors.

Home to historic inns and quaint B&Bs, St. Michaels is famous for its hospitality. The crown jewel among them is the Inn at Perry Cabin, an early 19th century manor home turned luxury getaway. While it attracts guests from all over the world, locals love it for its fine dining, gorgeous grounds, and postcard views.


Why we love St. Michaels.

The following are just a few of our favorite places to raise a glass, dine with friends, and celebrate the seasons of St. Michaels.

St. Michaels Winery is “local wine done right.” Good people, happy to share their passion for wine. Stop by for a tasting. Bonus: an easy walk or bike ride from San Domingo Cove.

Chesapeake Bay Maritime Museum is a must visit as you get to know St. Michaels. Interact with shipwrights in a working boatyard. Become a member and you can even dock your boat in their marina.

St. Michaels Harbour Inn, Marina & Spa. If you want to know what it’s like to wake up on the water, start with an overnight stay here. Then come on back to San Domingo Cove and experience it every day in your own waterfront home.

The Crab Claw Restaurant has been a St. Michaels institution since 1965. The place to go for steamed crabs, clams, oysters, award-winning crab cakes, and ice cold beer on the waterfront.

Marker 5. When you live in San Domingo Cove, you come to expect great views and Marker 5 delivers. Enjoy fresh, local cuisine in a casual setting right on the water. Bonus: over 30 beers on tap.

Ava’s Pizzeria & Wine Bar puts a sophisticated twist on the humble pizza pie. Named best new restaurant in 2008, it’s widely popular among locals and tourists alike.

The Inn at Perry Cabin is recognized as one of Maryland’s finest luxury resorts. As a local, you’re always welcome to enjoy its fine and casual restaurants, annual events, and world class spa.

Events & Festivals keep your social calendar hopping all year long. The following are just a few of the gatherings you can enjoy minutes from your new home at San Domingo Cove:

  • Celebrate St. Michaels' maritime heritage at events like Bay Day, Oyster Fest, and the Antique & Classic Boat Festival.
  • Foodies will love Talbot Restaurant Week, the annual Wine Fest at St. Michaels, and Brew Fest with live music and curated craft beers from all over the country.
  • The St. Michaels Art League hosts a fabulous Labor Day art show, along with classes and events for members all year long.
  • For classic car lovers, the Concours d’Elegance is a must attend “garden party celebration” at The Inn at Perry Cabin.