- Distance from Boston: 128 miles
- Best time: April to October
- Best for: Girl's GetawayRomanticFood and Wine
Tucked away on the shores of the Chesapeake Bay, this down-to-earth Maryland waterfront town perfectly blends the old world (think Naval Academy tall ships parading down the bay) with the new school (the local cuisine and shopping rival anything you can find back home). Annapolis is close enough to several cities to get a diverse mix of visitors, but steeped enough in its own traditions—it is the state capital, after all—to bring a unique flavor to your weekend. Grab your girlfriends, pack light, and take lots of photos on these quaint cobblestone streets. – By Elana Schor
Annapolis Cheat Sheet
View a printable list of all sights, restaurants, entertainment, and hotels from this itinerary. View
1Find your perfect treat at one of the boutiques and quirky general stores of the downtown shopping district. Culinary inspiration abounds at the Spice & Tea Exchange, and the Pink Crab offers flirty sundresses perfect for dashing around town.
2You've probably worked up a thirst, and luckily Level Lounge is there for a can't-miss happy hour. Try the baked apple pisco sour or the pomegranate caipirinha, but don't get too full on small plates like the caramelized onion gnocchi . . .
3. . . because you won't want to miss the feast of fresh Chesapeake crabs on offer at Cantler's Riverside, just a few minutes' drive from the water. Forget the tourist traps downtown, with their highway-robbery prices—the relaxed vibe and outdoor seating here make it an unbeatable place to watch the sunset.
1Start the day with waffles and local art at coffeehouse-and-gallery 49 West, where the baked goods are all homemade and the photography is dominated by talented locals.
2It wouldn't be a girls' weekend without a little men-in-uniform-watching, right? Put on your whites to go soak up the history during a tour of the storied Naval Academy. Senator John McCain and former President Jimmy Carter are among the famous alumni whose adventures are frequently invoked by talented tour guides.
3A lusher taste of the city's past is on view at the William Paca House and Garden, where you can stop and smell the flowers in a sumptuous two-acre spread of trees and flowers that dates back to the eighteenth century.
4Pick up lunch at Giolitti's, an Italian deli renowned by locals for sandwiches that range from meatball subs to piquant Cuban paninis.
5Get out on the water with a two-hour sailing cruise on the Schooner Woodwind. Check the calendar online for your ideal experience, whether it's a sunset sail or a French-wine-tasting afternoon.
6Kick back and compare notes (or souvenirs) before heading out for noodles and spicy lettuce wraps at "modern Thai" hotspot Lemongrass. Make sure to cool that fire with one of their fun cocktails.
7Keep the night rolling with some live music at the downtown Rams Head Tavern, one of the nation's best small clubs, where the acts range from country to acoustic to funk.
1Brunch in seaside style at the Severn Inn on the waterfront, famous for its views of the Naval Academy campus and its decadent buffet.
2Swap your favorite stories from the weekend over a pedicure or eco-friendly massage at Varuna Aveda Lifestyle Salon and Spa, where the organic Aveda products will transport you to a permanent vacation.
3For a bit of outdoor relaxation on your way home, stop by Quiet Waters Park with a glass of wine or treat for a brief picnic or a stroll along the hiking trails.
Where to Stay
For location and price, you can't beat Gibson's Lodgings, (rooms from $129/night), where several of the houses-turned-guest suites come with kitchens, and both parking and a continental breakfast are free. The center of downtown is within walking distance.
To splurge in high style, try The Annapolis Inn (rooms from $259/night). You'll feel like a modern-day Marie Antoinette stepping from the marble bathtub into a plush robe and relaxing on the exquisite silk couches that line its rococo suites.
When to Go
Like its western neighbor, Washington, D.C., the town can get downright swampy in summer and sleepy in winter. The best time to hit Annapolis is in the spring and fall, when a bevy of special events bring convivial crowds to the shore.
In April, stop by the annual croquet match between the Naval Academy and St. John's, or wait until May for the local Maritime Festival and a cavalcade of celebratory cadets during Commissioning Week.
Fall brings the annual United States Sailboat Show, usually in early October, and a fall festival that peaks with Halloween Eve festivities.
How to Get There
By car from Washington, D.C.: Annapolis is about forty-five minutes from Washington D.C. Take Route 50 East into Maryland until Exit 24, which leads you into town.
By car from Philadelphia: Annapolis is about two and a half hours from Philadelphia. Take I-95 South toward I-97 South and the Bay Bridge, which will take you to Route 50 East. Exit 24 will then take you into town.
By taxi (within town): Most destinations are within a ten to fifteen minute drive from downtown and can be reached by local taxis. We recommend Annapollis Cab Company (410-268-0022).