CRUISING

Annapolis & Eastport

This famed historic downtown houses the Naval Academy as well as too many shops and restaurants to count. Go for decadent brunch or fresh seafood in downtown Annapolis, and fine meats and oysters in Eastport. For casual fare, try the Boatyard Bar and Grill or Davis' Pub in Eastport or Chick 'n Ruth's Deli and Sofi's Crepes downtown Annapolis. Take your kids for a cruise on the pirate ship that tours the Severn River, then check out one of several ice cream shops along Main Street downtown. For pets, go to the Sea Dog Pet Boutique, and for the book lover visit Old Fox Books on Maryland Avenue. Tour the State House or follow the footsteps of America’s Founding Fathers as you wander the streets of downtown to learn more about the history of the capital of Maryland.

Kent Narrows

generations. The abundance of yacht yards and marinas will leave no boater behind. As for lodging, the Hilton Garden Inn Kent Island and Hyatt Place both offer all-encompassing amenities. The Chesapeake Bay Environmental Center and Ferry Point Nature Park are great launch spots for paddlers, while SipAhoy TikiBoat will provide a captain and a waterside tour as long as you provide the beer, wine, snacks and friends. When finished with fishing off boats, or exploring the various nature parks, visit The Narrows Restaurant or the Harris Crab House for fresh seafood.

St. Michaels

Cambridge

Kent Narrows might be known for its abundance of dock bars, cruising boats and happy hours that last into the wee hours, but it’s also the domain of watermen that have been harvesting the Bay’s bounty for

St. Michaels is one of the most popular weekend retreats for boaters, families and couples, featuring shops, restaurants, B&Bs and an elegant resort, accompanied by three marinas. For an elegant stay, visit the Inn at Perry Cabin, and for an experience with all amenities imaginable, choose the St. Michaels Harbor Inn, Marina and Spa. Notable restaurants include Foxy’s Harbor Grille and Ava’s Pizzeria and Wine Bar. The town’s crown jewel is the Chesapeake Bay Maritime Museum, where you can climb aboard the Hooper Island Straight lighthouse or take a ride on a traditional Bay boat. Shop on Talbot Street for microbreweries, ice cream parlors, antique shops, boutiques and art galleries.

As one of the earliest English settlements, Cambridge is a delightfully walkable town with restaurants, museums and a rich history. To be within walking distance of nearly everything in town, park the boat at Cambridge Yacht Basin. If you’re interested in the oldest working crab processing factory in the world, visit J.M. Clayton Company Seafood. For a quiet stay, visit Cambridge House Bed and Breakfast, or visit Hyatt Regency Chesapeake Bay Resort, Spa and Marina for a standalone, all-encompassing experience. The nearby Blackwater National Wildlife Refuge, a wildlife sanctuary, provides guided paddle tours where you’re sure to see bald eagles and migrating waterfowl. Learn about the life of the heroine who guided scores of enslaved people to freedom on the Underground Railroad at the Harriet Tubman Museum. The nationally renowned RAR Brewing originated here, while Blue Ruin specializes in delightful cocktails. Try the Portside Seafood Restaurant for the best in fresh seafood.

Solomons

The tiny island of Solomons Island hosts boats of every kind, restaurants full of fresh seafood, a boardwalk, and a downtown of shops and hotels. For the kids, visit the Calvert Marine Museum to see river otters, skates and rays, touch a giant fossilized shark’s tooth or take a ride on a traditional Chesapeake Bay buyboat. The island is both charming and entirely walkable, making the multiple marinas, B&Bs, marine museums, boardwalks and restaurants easily accessible. For the inner scientist, be sure to visit the Chesapeake Biological Lab, featuring seminars and tours. With plenty of options for food, be sure to check out highlights such as The CD Cafe, and Charles Street Brasserie.

Onancock

the weekend market, take in a flick at the historic Roseland movie theater, or tour the historic Ker Place. Do not miss the Corner Bakery, a cult favorite among locals and tourists alike. Bizzotto’s Gallery Cafe, Mallards at the Wharf, the Blarney Stone Pub and 3 Knots Taphouse are all local staples for dining and companionship.

Cape Charles

Urbanna

Although small, Onancock is wellloved. Surrounding by marshes and populated by restaurants and shops, it is popularly explored by foot and bikes. Due to the easy boat access, Onancock Wharf and Marina is an option for overnight lodging, as is the Charlotte Hotel, which features two dining rooms, a lovely bar and eight guest rooms. Onancock also provides an abundance of B&Bs like the Inn at Onancock with tastefully decorated with international themes. When exploring by water, launch your personal paddle-able boat or rent one from Burnham Guides, or climb aboard a cruise with Holly Cove Charters or Onancock Sailing Adventures. Visit Market Street for an abundance of galleries, stroll through

Cape Charles is a charming village filled with shops, restaurants and one of the best Bay beaches. The Cape Charles Yacht Center offers comprehensive marine services, while the Oyster Farm Marina at Kings Creek offers fresh seafood in a waterfront setting. Hotel Cape Charles and Bay Haven Inn provide charm and great breakfasts. Southeast Expeditions offers unique paddle tours, or go fishing on one of Cape Charles’s fleet of charter boats. The town boasts a half-mile-long white sand beach, complete with a fishing pier. In addition to the beach, Cape Charles is home to shops such as Table and Tonic, Lemon Tree Gallery and Peach Street Books. The quaint Central Park, Cape Charles Museum and Cape Charles Library provide lovely views, unique architecture and deep history. Cape Charles Distillery and Kelly’s Gingernut Pub are both friendly spots for a refreshing quaff. The Shanty, and Deadrise Italian Kitchen are the locals' favorite restaurants.

Although 75,000 people make the trek to the Urbanna Oyster Festival every October, there is much more to this charming town than just oysters freshshucked on the half shell, roasted, fried or stewed. If you’re looking for a place for the boat to stay, check out Bridge Marinas. If you’re looking for a place to stay check into The Chesapeake Inn, or look to the Bethpage Camp-Resort for cottages and even a waterpark. Walk around town to take in its rural charm, or launch a paddle from multiple launches. Something Different specializes in “Fine Neanderthal Cuisine,” Where the Sidewalk Ends provides delicious baked goods, and Marshall’s Drug Store’s lunch counter offers some of the best milkshakes around. And of course, if you find yourself in Urbanna in October, check out the world-famous Oyster Festival.

Deltaville

With possibly more boats than people, Deltaville proudly claims itself to be the boating capital of the Chesapeake Bay. Although there is no downtown in Downtown Deltaville (a hint to its scarce population), the town features