Visit the Annapolis City Dock on a day trip.
Updated: This article, which first appeared in the May 2019 issue of The Washingtonian, was updated in July 2022.
Annapolis: Discover Naval History and Sleep on a Boat
This seaside town is all about historic streetscapes and bustling marinas. 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.
Immerse yourself in American history
The William Paca House (186 Prince George St; 410-990-4543)a Georgian mansion where one of the signers of the Declaration of Independence lived houses a treasure trove of 18th-century furniture and a delightful walled garden.
Best place to ogle yachts
Pick up a charcuterie platter at the 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 sailors come to see and be seen.
A side of politics with your balls
Chick & Ruth’s Delly (165 Main Street; 410-269-6737), a split-level downtown diner just steps from the State House, is an Annapolis institution. Breakfast includes the Pledge of Allegiance, recited at 8:30 a.m. on weekdays and 9:30 a.m. on weekends, crab omelettes served three ways, and plenty of political gossip.
Great dinner by the water
On the shaded deck overlooking Carrol’s Creek Marina, enjoy phyllo-topped scallops served with a creamy shrimp sauce (410 Severn Ave; 410-263-8102). Visit 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, including Galway Bay (63 Maryland Avenue; 410-263-8333)where you can pair a pint with delicious fish and chips, and Boatyard Bar & Grill (400 4th St; 410-216-6206)serving thirsty sailors since 2001.
New ways of getting around
Hop on 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 drop you off at the docks drive along. On weekends the taxi runs until midnight (1 Dock St; 410-263-0033).
Sleep well on the water
When you book an overnight stay with Sail Away Catamarans (410-956-9323), Not only do you spend the night on a luxury boat, you wake up to a breakfast cruise on the Chesapeake Bay.
Queen Anne’s County: Party, Paddle and Pamper
East of the Bay Bridge, this county is the East Coast’s answer to Key West. Two of the best party bars on the waterfront, Jetty Restaurant & Dock Bar (201 Wells Cove Road, Grasonville; 410-827-4959) and Dock Bar by Red Eye(428 Kent Narrow Way N, Grasonville; 410-827-3937)have water views, palm trees, live music and crabs—and keep the celebrations going well past midnight.
space for paddling
Boat traffic is light on this side of the bridge, providing a quiet spot for kayaking. Those up for 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 about 19 miles round-trip. Or rent a kayak or canoe at the Chesapeake Bay Environmental Center (600 Discovery Lane, Grasonville; 410-827-6694)which provides water hiking maps for the surrounding waterways.
Where to raise a hammer
Join elbow-to-elbow with fellow crab crackers on the shore deck of the perennially busy Fisherman’s Crab Deck (3032 Kent Narrows Way S; 410-827-6666)a local favorite.
Familiarize yourself with the bay
A boardwalk at the Chesapeake Heritage & Visitors Center (425 Piney Narrows Road, Chester; 410-604-2100) leads to a small sandy bay. Learn about the bay’s ecosystem at the visitor center. 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 Road, Stevensville; 443-249-5757)you can treat yourself to budget packages like the Hemp Health Package, which includes a 50-minute CBD massage, a 50-minute CBD facial, and a glass of bubbly for $285.
The best places to stay
Next to its spa, the boutique Inn at the Chesapeake Bay Beach Club (410-604-1933) offers loft-style rooms near the bay. It’s also home to Queen Anne’s premier farm-to-table restaurant, Knoxie’s Table. The recently opened Kent Island Resort (500 Kent Manor Drs, Stevensville; 410-643-5757) has 26 airy rooms in a 200-year-old waterfront mansion. The 18Twenty Restaurant features fish from the bay and produce from local farms.
Cambridge: Historic and hip
This up-and-coming East Shore has a growing number of restaurants and shops anchoring historic downtown areas. Its nighttime atmosphere is at least partially fueled by RaR Brewing (504 Pappelstrasse; 443-225-5664), which hosts live music and opens its windows every night so the party can spill onto the sidewalk. The taproom serves a selection of about a dozen house-made IPAs and stouts, as well as the occasional dessert ale.
where to wake up
Early risers can head to Black Water Bakery (429 Rennstrasse; 443-225-5948), which opens at 7am for flavorful breakfast flatbreads with locally roasted coffee. Connoisseurs often order a homemade brioche bread to take away.
Get on the water
Sail aboard the Nathan of Dorchester at sunset (Long Wharf; 410-228-7141)a beautiful recreation of a historic Skipjack Boat navigating the scenic Choptank River.
Poplar bistro (535 Pappelstrasse; 410-228-4884) is an inviting boîte serving tapas with a French twist, like classic onion soup and ginger-marinated salmon. Ava’s Pizzeria & Wine Bar (543 Pappelstrasse; 443-205-4350), one of St Michaels’ most popular restaurants, has brought the same addictive pizza crust that’s risen in an 800-degree oven to its Cambridge location. For old-school East Coast Maryland crab chowder and rockfish to sprinkle with Old Bay, you won’t do anything better than a table at the no-frills Jimmie & Sook’s (527 Pappelstrasse; 410-228-0008).
The walkable downtown makes it easy to explore the growing number of indie boutiques such as Honeybee Trading Post (432 Rennstr.; 410-330-4459), where you can taste locally produced honey. If you time it right (Thursdays) you can spend the afternoon lounging by the water and perusing the Long Wharf Farmers’ Market (2 Yacht Club Drs; 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 will appreciate the swimming pools, mini-golf, game room, and small beach, while couples can seek oasis at the spa or on the greens, where carts have been newly outfitted with GPS screens.
Talbot County: Crabs and Culture
This county’s towns, such as St. Michaels and Easton, are known for their art, history and culture. Catch big-name acts like Arlo Guthrie at the intimate 380-seat Avalon Theater (40 E. Dover Street, Easton; 410-822-0345) and see great artwork without the crowds at the Academy Art Museum (106 South St., Easton; 410-822-2787).
Start your morning at Rise Up (618 Dover Road, Easton; 410-822-1353) with a touch of organic, fair trade coffee, roasted on site. The unpretentious café has communal tables; A food truck out front serves vegan burritos as well as classic breakfast sandwiches.
Crab cracking by the water
Whether you arrive by boat, car, or on foot, the harbor deck at Crab Claw (304 Burns Street, St. Michaels; 410-745-2900) is a prime spot for a traditional crab festival.
Catch a cheap boat trip
Climb aboard the Oxford Bellevue Ferry (101 E. Strand Rd., Oxford; 410-745-9023), which carries the wide, tranquil Tred Avon River from the city of Oxford to the tiny hamlet of Bellevue. The fare is $3 for pedestrians and $12 for cars, and the deck is one of the best places to spot ospreys diving for fish and herons stalking the shores.
Celebrate African American history
Take a self-guided walking tour of Easton’s Hill neighborhood, home to the nation’s oldest community of free blacks, dating back to the 1790s. A map showing the major buildings along the route is available at the Talbot County Visitor Center (11 S. Harrison St.; Easton; 410-770-8000).
Date night perfected
A romantic evening begins at chic Bas Rouge (19 State Road, Easton; 410-822-1637)where you can dine on Pillowy Blinis covered in Osetra caviar, followed by an after-dinner drink at just steps away steward (3 State Road, Easton; 410-793-4128)an elegant bar with 117 types of Scotch and vintage champagne.
Satisfy your sweet tooth
Order a dizzying sundae at Justine’s (106 N. Talbot St., St. Michaels; 410-745-0404) or an exotic homemade ice cream – dill pickle, anyone? – at the Scottish Highland Creamery (314 Tilghman St, Oxford; 410-924-6298).
Wake up to the water
The upscale Inn at Perry Cabin (308 Watkins Ln., St. Michaels; 410-745-2200), with waterfront suites, a leisurely spa, tennis courts, and a PGA-rated golf course, also has an ambitious sailing program. The retro chic Wylder Hotel (21551 Chesapeake House Dr., Tilghman Island; 877-818-1922)who has a room overlooking a marina has secured a coveted spot Conde Nast Traveler’s Reader’s Choice Awards.