St. Michaels charms visitors with its scenic city centre and prime location along the Chesapeake Bay. Tour the 18-acre waterfront Chesapeake Bay Maritime Museum, celebrating the culture of the bay with interactive exhibits, boat rides, demonstrations and more. Shop the unique boutiques and galleries before a tasting at the town’s winery, brewery and distillery. End the day with a delicious meal at one of many award-winning restaurants.

In the 1600s Captain John Smith called the area of Onancock “the Gem of the Eastern Shore” and today, Budget Travel calls it “The Coolest Town in the South.” This small town delivers on the relaxed Eastern Shore atmosphere but still has plenty for visitors to enjoy – live theatre, world-class restaurants, museums and a varied arts scene.  For a unique experience, travel by kayak to a local winery or the site of a Native American village. 

Settled in 1684, Cambridge is one of the oldest towns in Maryland and its rich maritime heritage can be explored in museums, historic district tours and river cruises. Set against a picturesque waterfront, the historic city centre is home to unique shops and galleries including the Dorchester Centre for the Arts. Cambridge is also home to the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina (shown here) — a premier four-diamond resort filled with opportunities for recreation and relaxation.

Accessible only by water or air, this tiny Chesapeake Bay Island is considered the “soft crab capital” of the nation. Here, watermen have harvested the water for generations and visitors can enjoy the bounty at the island’s restaurants. Rent bikes or “Tangier taxis” (golf carts) to cruise the nearly carless isle along narrow streets. Relax on the pristine shores, scout for Native American arrowheads or take a nature cruise. 

Stroll the boardwalk of this village in southern Maryland for waterfront views, shops and restaurants. See world-class art at the Smithsonian museum-affiliated Annmarie Sculpture Garden & Arts Center, a forested sculpture park featuring world-renowned artists. Explore local lighthouses including one of the last remaining “screwpile” lighthouses in the Chesapeake Bay or collect fossils along the beach near the Calvert Marine Museum.

This tiny fishing town is steps away from the Atlantic Ocean and is known for its herds of wild ponies made famous in the novel and film, Misty of Chincoteague. Along the wildlife refuge and national seashore, visitors can bicycle, fish, sunbathe or simply watch the ponies, migratory birds and other wildlife. Or head to nearby Wallops Island to watch rockets launch into space from the NASA Wallops Visitor Center.

Cape Charles is home to the only public beach on the bayside of Virginia’s Eastern Shore. Located in the historic district, the free public beach meets the shallow, calm waters of the Chesapeake Bay, making this an ideal coastal destination for families with small children. Area attractions include the Eastern Shore National Wildlife Refuge and Kiptopeke State Park, home to off-shore reefs constructed from concrete ships.

Kent Island is the largest island in the Chesapeake Bay and the site of the first European settlement in what is now Maryland. The annual Kent Island Day in Stevensville celebrates its 1631 founding each May with a parade, exhibits and other activities. For modern-era fun, golf, watersports, art galleries and seafood-laden restaurants are all highlights.