Tucked between the Delmarva Peninsula and the mainland coasts of Maryland and Virginia lies a string of gorgeous islands worth a hop, skip, and a ferry ride over. Discover the deep magic of Chesapeake Bay on these five amazing little islands.
Solomons Island packs a lot into a tiny package. At just two square miles, the town is home to a marina, marine museum, a winery, restaurants, boutiques, and the famous Annmarie Sculpture Garden & Arts Center (which showcases rotating works from the Smithsonian and the National Gallery of Art). Don’t miss a stroll down the island’s weathered riverwalk or a stop at aptly named (and delightfully anachronistic) Tiki Bar for a refreshing Mai Tai.
Photo: Ashley Eskridge
Those looking to truly escape should look no further than Tangier Island, a place where Wi-Fi, traffic jams, and crime are apparently non-existent (although neither is alcohol, so plan ahead). The island calls itself the soft crab capital of the Chesapeake, and places to indulge in that moniker pepper the town’s modest downtown: Fisherman’s Corner’s crispy fried crab bites and soft-crab sandwich are favorites. Nearby, Four Brothers Crab House & Ice Cream Deck is a one-stop-shop for seafood, sweets, and gear rentals (such as bikes and crab pots) for indulging in afternoon exploration on land and water.
Photo: Dana Insley
Smith Island has a history that that goes back almost as far as the country’s original settlement in Jamestown, Virginia. Yet somewhere along the way, it became a place that time (and civilization) forgot. Now, just over 200 full-time residents live here, many descended from generations of watermen. Because of that, finding crab straight from the source is a cinch—Smith Island Crabmeat Co-Op offers fresh whole crabs, crab cakes, crab salad, and crabmeat by the pound. Just don’t forget the sweets: At Smith Island Baking Company, Maryland’s official state dessert—an eight-layer, chocolate-frosted cake—is dished out by the monstrous slice.
Photo: Jay Fleming
Just an hour drive from DC, this 31-square-mile island (the largest in the Chesapeake) is packed with activities to delight visitors. Explore it by bike on the Cross Island Trail, a 6.5-mile stretch that winds past the Chesapeake Heritage & Visitor Center, through wetlands and wildlife, and drops you at Terrapin Park, where you can bask on a narrow stretch of sand. Reward your workout with a tour and rum tasting at Blackwater Distilling, then Uber over to one of the area’s many beloved restaurants—Hemingway’s (local icons Harris Crab House and Kentmorr Restaurant, too) is a great spot to nosh on fresh seafood while admiring the sunset.
Photo: Jay R. Shotel
This three-mile spit of land maintains a quiet existence compared to its trendy northerly neighbors—which is precisely why the locals love it. Terrestrial to-dos include the Tilghman Watermen’s Museum and a handful of laid-back eateries (try the crab and corn fritters at Mike & Eric’s Bay Hundred) but the real draw is out on the water. Take a day sail on the oldest skipjack on the Bay, the 19th-century Rebecca T. Ruark, or cruise with Chesapeake Lights Tours for old lighthouses (and BYO wine!).