Introduction

Colonial charm meets cosmopolitan flair in Annapolis—but make no mistake: this ain’t Williamsburg. Sure there are stunning period homes—tons of them—but you’ll also find chic restaurants and happening nighttime music venues so hip, they’ll be passé by morning. Docents in white stockings and powdered wigs stroll the red-brick streets, alongside women in power suits at State Circle, and families feeding ducks at City Dock. Maryland’s state capital is also the sailing capital of the world, and its harbor teems with sleek yachts, historic tall ships, and every other watercraft imaginable.

Cruise aboard a historic schooner or posh yacht, tour Revolutionary War-era homes, shop for cool gifts at myriad boutiques, and sample some of the Eastern Seaboard’s freshest seafood and sushi too. But you can’t do it all in one weekend. Better to hit the places you can, without over-scheduling your time, then return once the seasons change and transform the city’s tenor.

A note about geography: Annapolis juts into the Chesapeake Bay like a left-hand forefinger and thumb. The Naval Academy occupies the fingernail; State and Church circles form the knuckles; and West Street—nightlife central—takes up the rest of the finger. The thumb is the waterfront community of Eastport, a walkable neighborhood with happening cafes and the Annapolis Maritime Museum.

See & Do in Annapolis

Annapolis is best seen on foot: traffic is awful. The city is a quagmire of circles and short streets that abruptly dead end. Spare yourself frustration by parking in a garage or lot. (There’s one at the Visitors Center, and one at the Rams Head Tavern, at Clay and Washington streets, ideal if you’re in town for a concert.) If you insist on driving, you may miss the magical small details that make Annapolis worth visiting—a hidden alley, lush with black-eyed Susans, or an oxidized plaque detailing the historical import of where you happen to be standing.

The city is rife with Colonial history. A hotbed of political activity during the Revolutionary War, it was as happening then as New York City is today. The historic section encompasses City Dock, the State House, and Naval Academy. Start the day with a nutty Chesapeake Blend cup o’ joe at City Dock Coffee, then check out the slightly freaky bronze statues surrounding the Kunta Kinte memorial (from Alex Haley’s novel, Roots) at City Dock’s water’s edge. Ogle the sleek, 100ft luxury yachts lazing in the water—they don’t call this inlet ‘Ego Alley’ for nothing. When it’s sunny outside, you’re guaranteed a glimpse of how the other half lives—the beautifully tanned, moneyed, and privileged laze on the decks of their yachts, looking like Paris Hilton in Cannes Don’t believe me? Check out this web cam for a view of the show.

Restaurants, shops, and antique stores a-go-go surround Market Square and line Main Street, the latter a mainstream shopping corridor of chain clothing stores and touristy trinket shops. Check out the wild, contemporary sterling-silver bracelets at Blanca Flor. If you love wine, don’t miss Mills Wine, which carries hard-to-find varietals like rubaiyat. And there’s even free valet parking on weekends.

I’m normally hesitant to hype organized tours, since I prefer to make my own on-the-ground discoveries, but Annapolis has some great ones. See the city the way you ought to—by boat, aboard the historic Schooner Woodwind for two-hour sails during which you’ll get a chance to work the rigs, if you want to. Get schooled in early-American history on a walking tour with Capital City Colonials. If you’re addicted to tabloids and scandals, take their ‘Colonial Gossip’ tour. Or hop aboard a horse-drawn carriage with Annapolis Carriage for 20- to 50-minute journeys through cobblestoned circles and narrow passageways. During summer’s steamy heat, take the air-conditioned trolleys from Discover Annapolis Tours.

Two prestigious academic institutions call Annapolis home. The most famous is the United States Naval Academy. Post-September 11 security is tight—you can’t get in without a picture ID if you’re over 16—but you can still access plenty of the grounds. Start at the Armel-Leftwich Visitor Center, just inside Gate 1, at the end of King George St. The center is chock full of all things Navy; it’s also where tours of the Academy Yard begin. Arrive in time to see the Noon Formation, when the men and women in white line up for lunch. If you, like me, are a sucker for men in uniform, you’ll love it. Oh, and don’t expect to spot any familiar locales from the film Annapolis (2006). All the scenes, including the ones supposedly of the Naval Academy, were shot in—get this—Philly. Go figure.

St. John’s College is a quiet, picturesque institution whose academics are structured entirely around the readings of classic texts. The surroundings mirror the curriculum—-think Ivy League, with centuries-old brick buildings, one of which once housed Maryland’s colonial governor. For a dissection of the post-Homer epic or metaphysics for the modern age, listen in on a free lecture, Friday nights at 8:15pm, at the Francis Scott Key Auditorium. Key not only penned our national anthem, he was also a student here.

Annapolis is home to myriad boat races. The America’s Cup and the worldwide Ocean Volvo Race are two of the most prestigious—but the latter won’t return to the city until May 2008. In the meantime, check out racing schedules for the Eastport Yacht Club, Annapolis Yacht Club, and the Boatyard Bar & Grill for local events throughout the year—the latter of which hosts the popular Wednesday night summer races.

What a success story! Ten years ago, you’d not be caught dead on West Street Corridor—unless you were looking to score illegal pharmaceuticals or a pay date. Today, West Street is ‘new’ Annapolis—a hotbed of fresh culinary finds, live-music venues, and upscale, indie shops that are way more interesting than anything on Main Street.

Chi-chi Astrid specializes in designer duds from abroad. Object carries tchotchkes and gag gifts, including band-aids shaped like bacon strips! Pick up hand-crafted jewelry boxes, Annapolis-inspired vitreography (paintings on glass), and pottery inspired by Maryland’s famous crustaceans at Artfx. If you’re here on a romantic weekend, find a silky new outfit to impress your sweetheart at a la mode.

Annapolis has some fabulous historic homes—all of Maryland’s signers of the Declaration of Independence had houses in the Annapolis area, and they still stand today. One of the best ways to see them is on a tour with the Historic Annapolis Foundation.

The Hammond-Harwood House is an elegant town home that is one of the most complete examples of early American architecture. Built with tobacco money in 1774, it survived the Revolution and even a short stint as a St. John’s College fraternity in the early 1900s. Look for some cool period items like a leather fire bucket and an $8 bill. Wander the meticulously kept grounds of the William Paca House and Gardens. The five-tiered garden rolls down to the fish-shaped pond, topped with a white-picket bridge across its water.

Charles Carroll (as in Carrollton) and his family significantly shaped the state of Maryland. Politicians, lawyers, and businessmen, they were a little like the Vanderbuilts during the 1700s. Carroll was also the only Catholic signer of the Declaration of Independence. Check out his personal effect at his birthplace, the Charles Carroll House.

The Chase-Lloyd House, named for lawyer Samuel Chase—another Declaration signer—is now a home for retired women. Though only the first floor is open to the public, it’s worth a quick look for the impressive Georgian and Flemish architectural flourishes. The Banneker-Douglass Museum (free!) is in a beautiful old church with rotating and permanent installations on the history of African Americans in Maryland.

Annapolis Restaurants & Taverns: Eat Cheap

Rams Head Tavern ($-$$) is one of my favorites, not necessarily for the food, but for the music lineups ranging from surfing legend Dick Dale, to finger-pickin’ master Leon Redbone, to modern rock and country groups (all shows are 21+). It’s also a brewpub and the beers are phenomenal—order the Fordham sampler. The burgers and app’s are a couple of steps up from TGI Friday’s, but there are turkey burgers and tuna-steak sammies for those watching their waistlines. A better choice than the pub grub is the Galaxy Stew, with fat hunks of crab, shrimp, and scallops; or come on a Monday for half-price lobster night. Their happy hour is one of the best around—free food 5pm to 7pm, with microbrews priced under $2.

George Washington knocked a few back at Middleton Tavern ($-$$), a popular stopover with travelers along the Virginny-Philadelphia route in the 1700s. Sample the microbrews along with a hearty lunch of Old Bay-steamed clams, or slam oyster shooters at the bar. I prefer eating on the ’splintery’ covered porch outside and giggling at the young ladies checking out the Naval Academy plebes.

I feel like I’m in London when I visit the stately Reynolds Tavern ($$-$$$). It’s a Jeckyll and Hyde type of place, with a refined atmosphere on the first floor, and a raucous attitude down below in the Sly Fox Pub. Bangers and mash and fish and chips are staples in the pub, as are steamed mussels and quesadillas. Monday is half-price wine night, but if you prefer beer, go for the Sam Smith Oatmeal Stout. Back on the first floor, Reynolds’ serves a scrumptious high tea in a room with Victorian lace and floral-patterned wallpaper. Order the Colonial High Tea for the full treatment; aside from your choice of a bazillion teas—I recommend the ‘Gun Powder green tea—there’s also a mouth-watering plate of dense scones, crust-less sandwiches and a savory mini-quiche.

From governors to grandmothers, everyone who’s spent a lot of time in Annapolis has eaten at least once at Chick and Ruth’s Delly ($-$$). Expect thick hamburgers and apple pie, amazing crab omelets, and belt-busting ‘colossal’ sandwiches, which come with about two pounds of meat! This place is as American as it gets—every morning begins with a recitation of the Pledge of Allegiance.

Joss ($$-$$$) is the top spot for sushi, and a big glass window looks onto historic Main Street, perfect for people-watching. Rolls tend toward the exotic—where else can you get steamed monkfish liver wrapped in soy paper?—and there are more than 50 varieties to choose from. Save room for dessert: the grilled bananas will knock your socks off. Tsunami ($$-$$$) comes in a close second, mostly for its modern vibe and cheaper prices, but the service is s-l-o-w. Still, the West Street location makes this a convenient spot before a concert at the Rams Head Tavern.

I’ve not yet tasted the tapas at Kyma, but word has it that the small plates are miniature works of art. Check it out and let me know what you think!

How can you not love a place that throws full-moon parties? The Boatyard Bar & Grill ($-$$$) is a fun, casual hangout, wildly popular with the local boating set—it feels more like Key West than Maryland. Food is casual, dominated by finger-popping bites like conch fritters, fried shrimp and sinful Boatyard Cheese Fries topped with pepperjack cheese and hickory smoked bacon bits. I always dig the crispy soft shell crab sandwich (though the fixin’s are a little plain—lettuce and a Kaiser roll are a little flat). The restaurant is very active in the community, hosting races, fundraisers, and parties, and takes its environmental place in the world pretty seriously as a member of 1% For the Planet.

For steamed crabs, there’s only one name in town: Cantler’s ($$-$$$). And that’s saying something in this seafood hub. It doesn’t matter when you go, the crabs are always heavy and sweet. I love the paper-covered picnic tables and getting my hands grimy with Old Bay. On any given night, you’ll find it buzzing with the happy hour crowd and crab-feast seekers. I also love the fact that their kids’ menu lists fish munchies and steamed shrimp—with no utensils required.

Despite its airy-fairy name, Yin Yankee Cafe is a trippy, dark restaurant with décor dominated by fishtanks and water-inspired accents that put you in the mood for their incredible seafood. Choose from a large sushi menu. Parents: Kids l-o-v-e the funky PB&J sushi roll. Or go for hot entrees like ginger chicken, potstickers, banana-leaf or curry-roasted fish, and an awesome ‘crabchop’; a giant crabcake topped with tangy wasabi mashed potatoes. Yum!

Annapolis Restaurants: Splurge

The food is as crisp as the white walls and wood décor at chic Metropolitan ($$$). The menu changes with the seasons, but look for perennial favorites like prosciutto-wrapped scallops and inventive dishes like foie gras BLTs, and black-truffle-and-lobster risotto. If you can, sit on the rooftop deck: the food somehow tastes better when you’ve got an open-air, third-floor view of Annapolis’s teeming streets. NB: Cocktails cost a whopping $10 (or more).

Thai-influenced Lemongrass ($$$) shares ownership and sidewalk space with neighboring Metropolitan, and exudes a similar high-fashion vibe. Specialties include the lemongrass shrimp special (jumbo shrimp served with chicken and fat lumps of crabmeat) and the crispy whole rockfish—a delicious spin on this fav local fish. Vegetarians are well respected here and even get a full page on the menu, with entrees like fried tofu in kaffir lime leaves. A comprehensive selection of curries, noodles, and rice bowls rounds out the menu. If you have a sensitive stomach, let the waiter know: most of the dishes are spicy.

Annapolis Hotels

Annapolis has no true budget hotels. Stay near State Circle for proximity to downtown and West Street. Otherwise, there are chain hotels and motels farther west, but in my opinion they’re too far from the action.

The business-class Annapolis Marriott Waterfront ($$$-$$$$) is the only waterfront hotel in town. Perched smack at the end of City Dock, the hotel’s rooms are big, with balconies fronting on the Chesapeake Bay. And unlike at many chain hotels, here they use allergen-free, environmentally friendly cleaning products and linens. Downstairs, the bay-front bar and restaurant Pusser’s serves tropical cocktails so strong, they’d make Jimmy Buffet blush.

The vibrant, royal colors of the Lowes Annapolis Hotel fit in well on happening West Street. Rooms are minimalist but striking, with yummy Bloom toiletries and flat-screen TVs in some. An onsite spa indulges with special treatments like thermal stone facials and detoxing, ginger-essence massages. If you like to dine among local politicians and powerbrokers, make a reservation at the onsite upscale, dimly lit chophouse, Breeze.

Annapolis’ newest high-end hotel, the O’Callaghan Annapolis Hotel ($$$-$$$$) sports mahogany wood furniture, crystal chandeliers, and cool marble floors imported from Europe. Leather chairs complement a gold-and-navy-blue color scheme; high-thread count sheets adorn the bed. The hotel is tucked just off West Street, the new happening center of dining and nightlife.

A night on the Schooner Woodwind ($$$$) will literally rock you to sleep. The 74ft schooner is a little hostel-like, with cramped quarters and two shared baths (hand-held showers only). But if you book a night aboard the vessel, you’ll get to party with the sunset-cruise crowd, before disembarking for dinner around 9pm. But be back before midnight, lest you find yourself unable to re-board. Claustrophobes do better in a proper hotel.

Or book a weekend shipboard with a boat-and-breakfast cruise on La Bella Vita, moored just outside Annapolis. Cabins are plush, with wooden headboards and furniture, mounted bedside lamps, and private bathrooms. The Queen Mary it ain’t, but it does make rounds of fun waterfront towns like St. Michaels, where you can spend the afternoon shopping. Between towns, hang out on the deck, noshing on crab puffs and other tasty hors d’oeuvres. Stay aboard for dinner or disembark; menus change regularly, but you can guarantee the seafood dishes are freshly caught.

Annapolis Inns and B&Bs

Details are exquisite at the opulent Annapolis Inn ($$$-$$$$), from the Austrian crystal chandeliers to the koi pond dotted with lily pads. Rooms are done in Colonial style (welcome to Annapolis), with exposed brick fireplaces, claw-foot tubs and heavy four-poster beds, but there are also contemporary high-end amenities too, notably the bathrooms’ heated marble floors and towel warmers. Of all the rooms, the Rutland Suite is my favorite, if only for its wonderful private sundeck. If you’re looking for a place to pop the question, this is it. Oh, and check out the historic Underground Railroad tunnel, which still exists in the basement. Very cool.

The circa-1870 Royal Folly Bed and Breakfast ($$$) tricks you with its casual appearance of a private home. But its unassuming, blue façade belies five stylish suites. Popular and whimsical, the Queens Chamber suite has royal purple walls, with two fireplaces in the bedroom and bath, and a double Jacuzzi and personal bidet. The remaining four suites are splashed with vibrant reds, yellows, and blues, Jacuzzi tubs, and triple-sheeted four-poster beds. If you’re traveling with your pet, you can get the entire bottom floor to yourself. Linger on Sunday morning with champagne brunch and complimentary late checkout. A garden hot tub sweetens the deal. No kids under 18.

The William Page Inn ($$$) is stunning, with cream-and-burgundy striped awnings, a wraparound porch, cheery flowerboxes, and a lush mature garden with a gurgling fountain. Despite the common area’s clutter, the rooms are sweet and simple, with white eyelet bedspreads, mirrored vanities, pastoral artwork, and retro black metal fans. The atmospheric Maureen Suite, on the top floor, has big dormer windows and skylights. Best of all, off-street parking is included—a rarity in Annapolis. The inn is right next to the Naval Academy.

Vacation Rentals

Vacation rentals can be tricky to navigate, but the payoff is huge. Whether you’re a budget traveler who can’t afford the double-whammy cost of hotels and restaurants, or a luxury traveler who wants seclusion and over-the-top grandeur, you’ll get more space and privacy for your money by booking a rental property. And you’ll have a kitchen too. Read our vacation rentals how-to guide to find our how, and where, to rent.