Annapolis: Explore Naval History and Sleep on a Boat

This waterfront town is all about historic streetscapes and bustling marinas. You can tap into the spirit of the town at the United States Naval Academy (52 King George St.; 410-293-8687), the training ground for America’s midshipmen, which offers tours of “The Yard” that include a visit to the crypt of Revolutionary War hero John Paul Jones.

Soak in American History

The William Paca House (186 Prince George St.; 410-990-4543), a Georgian mansion that was home to one of the signers of the Declaration of Independence, holds a trove of 18th-century furnishings and has a superb walled garden.

Best Spot to Ogle Yachts

Grab a charcuterie platter from Annapolis Market House (City Dock; 443-949-0024) and stake out a spot on a bench across the street along Ego Alley, the narrow channel where yachters come to see and be seen.

A Side of Politics With Your Eggs

Chick & Ruth’s Delly (165 Main St.; 410-269-6737), a bi-level downtown diner steps from the State House, is an Annapolis institution. Breakfast includes the Pledge of Allegiance—recited weekday mornings at 8:30 and weekends at 9:30—crab omelets served three ways, and plenty of political gossip.

Great Waterfront Dinner

Enjoy phyllo-topped scallops served with a twirl of shrimp cream sauce on the shaded deck overlooking the marina at Carrol’s Creek (410 Severn Ave.; 410-263-8102). Hit the restaurant on a Wednesday evening for the best view of the summer sailing races.

Where to Catch a Buzz

Like any proper sailing town, Annapolis has its fair share of great bars, among them Galway Bay (63 Maryland Ave.; 410-263-8333), where you can pair a pint with tasty fish and chips, and Boatyard Bar & Grill (400 4th St.; 410-216-6206), which has been serving thirsty sailors since 2001.

Novel Ways of Getting Around

Hop aboard one of the city’s new open-air trolleys (free), grab a pay-per-use e-bike ($2), or hail a water taxi ($3) and get ferried along the harbor. On weekends the taxi runs until midnight (1 Dock St.; 410-263-0033).

Sleep Tight on the Water

When you book an overnight with Sail Away Catamarans (410-956-9323), you not only get to spend the night on a luxury boat, but you’ll also wake up to a breakfast cruise on the Chesapeake Bay.

Kayak on peaceful water at Matapeake State Park. Photograph courtesy of National Parks Conservation Association.

Queen Anne’s County: Party, Paddle, and Be Pampered

Just east of the Bay Bridge, this county is the Eastern Shore’s answer to Key West. Two of the best party bars on the shore, Jetty Restaurant & Dock Bar (201 Wells Cove Rd., Grasonville; 410-827-4959) and Red Eye’s Dock Bar(428 Kent Narrow Way N., Grasonville; 410-827-3937), have water views, palm trees, live music, and crabs—and keep the festivities going well past midnight.

Place to Paddle

Boat traffic on this side of the bridge is light, providing a peaceful site to kayak. Those up to a challenge can launch their kayak from Matapeake State Park (1112 Romancoke Rd., Stevensville; 410-758-0835) and paddle from the base of the Bay Bridge to a historic lighthouse for a round trip of about 19 miles. Or you can rent a kayak or canoe at the Chesapeake Bay Environmental Center (600 Discovery Ln., Grasonville; 410-827-6694), which provides water-trail maps for the surrounding waterways.

Where to Lift a Mallet

Join fellow crab-crackers elbow to elbow on the waterfront deck at the perpetually busy Fisherman’s Crab Deck (3032 Kent Narrows Way S.; 410-827-6666), a local favorite.

Acquaint Yourself With the Bay

A boardwalk at the Chesapeake Heritage & Visitors Center (425 Piney Narrows Rd., Chester; 410-604-2100) leads to a small sandy cove. Inside the visitors center, you can learn about the bay’s ecosystem. Outside, you can climb a tower for a bird’s-eye view.

In Search of Zen

At the stylish Spa at the Chesapeake Bay Beach Club (500 Marina Club Rd., Stevensville; 443-249-5757), you can indulge in well-priced packages such as the Hemp Health Package, which includes a 50-minute CBD massage, a 50-minute CBD facial, and a glass of sparkling wine for $285.

Best Places to Stay

Besides its spa, the boutique Inn at the Chesapeake Bay Beach Club (410-604-1933) offers loft-like rooms near the bay. It’s also home to Queen Anne’s best farm-to-table restaurant, Knoxie’s Table. The recently opened Kent Island Resort (500 Kent Manor Dr., Stevensville; 410-643-5757) has 26 airy rooms in a 200-year-old manor house perched along the water. Its restaurant 18Twenty features fish from the bay and produce from surrounding farms. 

Sign up for a sunset sail on the skipjack Nathan of Dorchester. Photograph courtesy of Dorchester Skipjack Committee.

Cambridge: Historic and Hip

This Eastern Shore up-and-comer has a growing number of restaurants and shops anchoring historic downtown spaces. Its late-night vibe is fueled, at least in part, by RaR Brewing (504 Poplar St.; 443-225-5664), which hosts live music and throws open its windows nightly, freeing the party to spill out onto the sidewalk. The taproom serves a selection of about a dozen house-crafted IPAs and stouts along with the occasional dessert ale.

Where to Wake Up

Early risers can head to Black Water Bakery (429 Race St.; 443-225-5948), which opens at 7 a.m. for spicy breakfast flatbreads paired with locally roasted coffee. Those in the know often order a house-made brioche loaf to go.

Get on the Water

Take a sunset sail aboard the Nathan of Dorchester (Long Wharf; 410-228-7141), a handsome replica of a historic skipjack that plies the scenic Choptank River.

Downtown Dining

Ava’s Pizzeria & Wine Bar (543 Poplar St.; 443-205-4350), one of the most popular restaurants in St. Michaels, has brought the same addictive pizza crust blistered in an 800-degree oven to its Cambridge location. Locals and visitors gather at Blue Ruin (400 Race St.; 410-995-7559) in downtown Cambridge. This fun, funky speakeasy-style bar and restaurant serves locally-sourced bites like deviled eggs topped with crab meat as well as craft cocktails, such as one called Good Ole Travers made small-batch whiskey and muddle sweet corn.

Tasty Souvenirs

The walkable downtown makes it easy to check out the growing crop of indie boutiques, such as Honey Bee Trading Post (432 Race St.; 410-330-4459), where you can try locally produced honey. If you time it right (Thursdays) you can spend the afternoon along the water pursuing the Long Wharf Farmers’ Market (2 Yacht Club Dr.; 443-477-0843).   

Best Place to Stay

Many rooms at the Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina (100 Heron Blvd.; 410-901-1234) have balconies overlooking the water. Families appreciate the swimming pools, miniature golf, game room, and small beach, while couples can seek out an oasis in the spa or on the greens, where carts have been newly outfitted with GPS screens.

Easton’s charms include history and art. Photograph courtesy of Talbot Tourism.

Talbot County: Crabs and Culture

This county’s towns, such as St. Michaels and Easton, are well known for their art, history, and culture. For example, you can catch big-name acts like Arlo Guthrie in the intimate 380-seat Avalon Theatre (40 E. Dover St., Easton; 410-822-0345) and see great works of art without the crowds at the Academy Art Museum (106 South St., Easton; 410-822-2787).

Healthy Start

Kick off your morning at Rise Up (618 Dover Rd., Easton; 410-822-1353) with a buzz from organic, fair-trade coffee that’s roasted on-site. The low-key cafe has communal tables; a food truck out front serves vegan burritos, along with classic breakfast sandwiches.

Waterfront Crab-Cracking

Whether you arrive by boat, car, or foot, the harborfront deck at the Crab Claw (304 Burns St., St. Michaels; 410-745-2900) is a prime location for a traditional crab feast.

The Eastern Shore is home to great crabhouses.

Catch a Cheap Boat Ride

Hop aboard the Oxford-Bellevue Ferry (101 E. Strand Rd., Oxford; 410-745-9023), which navigates the wide, placid Tred Avon River from the town of Oxford to the tiny hamlet of Bellevue. The fare is $3 for walk-ons and $12 for cars, and the deck is one of the best places to glimpse ospreys diving for fish and herons stalking the shores.

Celebrate African American History

Take a self-guided walking tour of the Hill neighborhood in Easton, home to the oldest community of free Blacks in the nation, dating to the 1790s. A map that identifies key buildings along the route is available at the Talbot County Visitors Center (11 S. Harrison St.; Easton; 410-770-8000).

Date Night Perfected

A romantic evening begins at chic Bas Rouge (19 Federal St., Easton; 410-822-1637), where you can dine on osetra caviar capping pillowy blinis, followed by an after-dinner drink steps away at the Stewart (3 Federal St., Easton; 410-793-4128), a sophisticated bar with 117 types of Scotch plus vintage Champagne.

Photograph courtesy of Scottish Highland Creamery.

Satisfy Your Sweet Tooth

Order a vertiginous towering sundae at Justine’s (106 N. Talbot St., St. Michaels; 410-745-0404) or an exotic homemade ice-cream cone—dill pickle, anyone?—at Scottish Highland Creamery (314 Tilghman St., Oxford; 410-924-6298).

Wake Up With a Water View

The upscale Inn at Perry Cabin (308 Watkins Ln., St. Michaels; 410-745-2200), with waterfront suites, a cozy spa, tennis courts, and a PGA-worthy golf course, also has an ambitious sailing program. The retro-chic Wylder Hotel (21551 Chesapeake House Dr., Tilghman Island; 877-818-1922), which has rooms facing a marina, snagged a coveted spot on Condé Nast Traveler’s Readers’ Choice Awards.