Dockside in Annapolis
Stay: Marriott’s Annapolis Waterfront Hotel is in the middle of the downtown action. The “waterfront balcony” rooms have tables for two overlooking Spa Creek—ideal for enjoying a room-service breakfast—and a new dockside restaurant, Armada Waterfront Tequila Bar & Cantina, is slated to open in the hotel in late summer.
Uptown on West Street, the recently opened 1313 West boutique hotel—in a renovated 19th-century farmhouse—has a modern but cozy feel. Its basement bar, open to hotel guests only, is inspired by New York City’s Polo Bar. In the morning, the unassuming Thai restaurant Carlson’s, just a block away, sells melt-in-your-mouth doughnuts—get there early and bring cash (and don’t sleep on the Thai food, either).
Dine: Right downtown overlooking the waterway called Ego Alley, the Choptank restaurant is especially popular among tourists for its spacious rooftop bar and two floors of waterfront dining. The area is also home to several other great spots, including Dock Street, which has good bar food, Vida Taco Bar, and Acqua Al 2, where a trendy, dimly lit basement bar is ideal for after-dinner drinks. A few blocks uptown, favorite dining destinations include the new upscale seafood spot SeaSalt, plus Timber Pizza Co., Tsunami for sushi, and Level for small plates. On Wednesdays in the summer, al fresco diners at the latter two can enjoy live music during “Dinner Under the Stars.”
Another day, hit a different neighborhood: The pedestrian-friendly Spa Creek Bridge connects the downtown area to Eastport, where the city’s best crabcake sandwich is at Boatyard Bar & Grill and Forward Brewing offers a casual indoor/outdoor spot for beer and cider. A slightly longer walk brings you to Vin 909, where locally sourced small plates and wood-fired pizzas are well worth the wait.
Do: Art galleries line West Street, which flows down to Main Street—where, among all the clothing boutiques and souvenir shops, Capital Comics is fun for little readers and Seasons has an expansive collection of high-quality oils and vinegars to try. From there, head to Maryland Avenue, where a slew of antiques shops and a record store await. Afterward, grab a pint at Galway Bay.
Shopping not your bag? Great Frogs Winery and Chessie’s Wharf, from RAR Brewery, both of which often host live music outdoors, are a short car ride away—as is Quiet Waters Park, with hiking trails, playgrounds, and a dog park and dog beach. In the evening, catch a show at the Annapolis Summer Garden Theater if it’s in season—the 59-year-old outdoor theater is downtown near City Dock. Or grab tickets to a concert at Rams Head On Stage. For pre-dinner drinks or bites, adjacent Rams Head Tavern has a nice, somewhat hidden patio.
Don’t miss: To find out about the city’s dozens of annual festivals and other happenings, check the Visit Annapolis website as well as the Inner West Street Association’s events calendar.
Exploring the Outdoors on Kent Island
Stay: Though it’s especially popular as a wedding venue, the Chesapeake Bay Beach Club also has a weekend-retreat-worthy inn. There are guest rooms in the main building and suites in a farmhouse-style structure called the Barn, as well as private cottages.
Dine: The hotel restaurant, Knoxie’s Table, is a destination in itself. Offsite, Kent Island and adjacent Kent Narrows are full of seafood restaurants with water views, ranging from beachy vibes (such as the Jetty) to more upscale dining (Bridges). Harris Crab House is a local favorite.
Do: The resort offers outdoor yoga on Saturday and Sunday mornings seasonally, as well as dipping pools and fire pits. Close by, the waterfront Mark Cascia Vineyards, open seasonally, hosts live music in the summer. Matapeake Clubhouse and Beach is home to a public swimming beach, plus a picnic area and a one-mile wooded trail with Bay Bridge views. Just down the road, the 600-foot-long Romancoke Pier is great for fishing and crabbing. Tip: Matapeake Beach and the Romancoke Pier are connected by the South Island trail, a paved path for biking. Nearby Terrapin Nature Park offers more walking and biking trails, in addition to a long stretch of beach. (The park makes for a nice day trip, too, if that’s all the time you have—see page 58 for that and other great ways to spend a day.)
Don’t miss: The resort’s full-service spa has a cozy, lounge-style relaxation room with a fireplace, plus private and group Himalayan-salt saunas.
A Trip to Chic St. Michaels
Stay: The new Wildset Hotel is a trendy addition to the St. Michaels scene, with its vintage-modern style. (The vibe is similar to that of DC’s Line and Eaton hotels.) Most rooms have a gas fireplace and a private balcony or terrace. Looking for a more posh experience? St. Michaels’ five-star Inn at Perry Cabin offers manicured grounds and sprawling water views.
Dine: In town, the Crab Claw is a quintessential waterfront spot for crabs, Ava’s Pizzeria & Wine Bar is a mainstay, and Foxy’s Harbor Grille has live music and an extensive menu of crush cocktails. Ruse, at the Wildset Hotel, is well loved, with an oyster bar and other Chesapeake Bay–inspired cuisine. At the Inn at Perry Cabin, options include a restaurant with a Chesapeake-inspired menu; a more casual bar and courtyard offering cocktails and small plates; plus a pool bar. For the most indulgent experience at the inn, book a private table at one of the riverside dining houses, where you’ll be served a five-course menu with wine pairings. Tip: Grab a bottle of wine and some glasses from the bar, then enjoy your own pre-dinner cocktail hour in the Adirondack chairs overlooking the water.
Do: Borrow a bike (both hotels offer them) to cruise the town. There’s lots of good shopping—particularly for home goods and antiques—along Talbot Street. For an aquatic adventure, Shore Pedal & Paddle offers standup-paddleboard and kayak rentals. At the end of the night, enjoy s’mores around a fire pit—the Wildset Hotel and the Inn at Perry Cabin both have them. And you needn’t be a guest to enjoy all that the Inn at Perry Cabin has to offer: You can play a round on the 18-hole golf course (and get lessons from a PGA pro), set sail on a skipjack, or spend a day at the spa.
Don’t miss: Among the many events the town is known for are summer concerts in the park, festivals at the Chesapeake Bay Maritime Museum, holiday festivities, and more—visit the St. Michaels Tourism website for details.
A Kid-Friendly Resort in Cambridge
Stay: There’s tons for kids—both youngsters and teens—to do at the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina, where the 550-square-foot family petite suites include a king bed and bunk beds.
Dine: The resort offers several options, including Michener’s Library, with its soaring windows overlooking the water; Water’s Edge Grill, which has kids’ menus and a cozy two-story fireplace; a casual bar and grill at the golf course; a grab-and-go market; and a seasonal restaurant plus two seasonal pool bars.
Do: Families can take a swing at the nine-hole mini-golf course, hit the playground, or take a dip in one of several pools, where you can rent a cabana and enjoy poolside drink and snack service. There are also tennis, basketball, and beach-volleyball courts; horseshoes; and walking trails—plus a full calendar of events, such as “dive-in” movies at the pool.
Don’t miss: The kids’ camp has half-day and full-day options. Children ages four through 12 can explore the pool, nature trails, the playground, and more, while parents can experience other amenities on their own, including the 18-hole golf course and a full-service spa.
Dinner and a Show in Easton
Stay: The Hummingbird Inn, a dog-friendly bed-and-breakfast that offers six rooms in a renovated Victorian, has a perfect five-star rating, with more than 400 reviews, on Google. The Tidewater Inn is another popular place to stay in Easton—it sits right along the action on East Dover Street and offers luxe accommodations.
Dine: In Washingtonian’s 2023 list of 100 Very Best Restaurants, our food team called Bas Rouge the “crown jewel” of Paul Prager’s “chic fleet of Easton restaurants.” It features a pricey but acclaimed tasting menu for dinner ($225 and up for three courses with wine pairings), plus an à la carte lunch. Other local favorites include Weather Gage, for coffee, freshly made pastries, breakfast sandwiches, and lunch, and Out of the Fire, which serves locally sourced salads, sandwiches, pizzas, and more for lunch and dinner. If you’ve got a spot to eat them, try Gay’s Seafood to pick up freshly caught and steamed crabs.
Do: Catch a live music show at the historic Avalon Theatre and an exhibit at the Academy Art Museum. You can also check out the shops downtown—walking distance from both inns. About 20 minutes away by car, hike a waterfront trail at Pickering Creek Audubon Center. In nearby Oxford, you can check out artwork depicting the lives and history of the region’s founding African American families at Water’s Edge Museum, enjoy ice cream from the Scottish Highland Creamery on a bench overlooking the water at Oxford Town Park, or catch a sunset over dinner at Doc’s Sunset Grill.
Don’t miss: Easton is home to a variety of events, from its regular farmers markets to the Waterfowl Festival, which makes the city a national destination.
A Summer-Camp-Inspired Visit to Tilghman Island
Stay: With almost ten acres of waterfront property and 54 rooms, the stylish Wylder Tilghman Island hotel is reminiscent of summer camp, but for adults and kids alike.
Dine: Right on the property, Tickler’s Crab Shack and Restaurant overlooks the water. Offsite, try breakfast or brunch at Two If By Sea and grab lunch to go at the deli in the Tilghman Island Country Store.
Do: Hotel guests are encouraged to have picnics on the grounds; take the paddleboards, kayaks, and canoes out to explore the waterways; kick back in the tree swing and other waterfront relaxation spots; pedal around town on the beach-cruiser bikes; and then gather around the fire pit. There are also lawn games and a private beach. Looking for a little more adventure? You can charter a boat directly from the property.
Don’t miss: The Tilghman Watermen’s Museum, created to convey the history of the island through photography, artifacts, and more.
This article appears in the May 2025 issue of Washingtonian.
Amy leads Washingtonian Weddings and writes Style Setters for Washingtonian. Prior to joining Washingtonian in March 2016, she was the editor of Capitol File magazine in DC and before that, editor of What’s Up? Weddings in Annapolis.
