Due east of Columbus, America's sailing capital offers bay views and big-time charm.
Every March, the boaters of Annapolis celebrate a quirky and beloved ritual. On the spring equinox, hardcore sailors gather on the shore of Spa Creek to herald the arrival of the season by setting their winter socks ablaze. After the recitation of a tongue-in-cheek “Ode to the Equinox” written just for the occasion, they raise a toast, roast some oysters and wriggle bare toes in deck shoes as their footwear goes up in smoke.
The genial author of the ode, Jeff Holland, says the tradition shows that the locals “appreciate a little anarchy”—not exactly what you'd expect in a town that's well-known for a military landmark. But Annapolis's joyful Sock Burning is just another reminder that the sea runs deep in the city's DNA. Life pulses to the tidal rhythms of the Chesapeake Bay, with the tempo quickened by the energy of a passionate boating community and the exuberance of 4,000 midshipmen at the U.S. Naval Academy.
Founded in 1649, Annapolis was one of the first cities in the country, and at City Dock, the heart of town, it's easy to see why it became an important early port. The harbor on the Severn River opens onto the wide Chesapeake Bay, America's largest estuary and the colonies' busiest waterway.
Captain John Smith and his crew explored the bay from 1607 to 1609, mapping almost 3,000 miles of shoreline. Just a few decades later, merchant ships carrying vital goods and correspondence filled the harbor, creating a vibrant center of wealth and culture once described as the “Athens of America.” Today, the vessels moving to and fro are likely to be pleasure craft or paddleboards, but Smith's glowing assessment of the region—“Heaven and earth never agreed better to frame a place for man's habitation”—is shared by all.
Get Your Feet Wet
There's no better place to appreciate Annapolis's nautical side than Ego Alley, the channel that connects the harbor to the foot of Main Street. Cruising the narrow waterway, boat owners proudly flaunt their yachts, trawlers and ketches while landlubbers admire their sleek lines (and clever monikers). If the season's right, you might spot an authentic skipjack, the workboat once used to harvest oysters under sail.
Jump right in and board the Harbor Queen for a narrative sightseeing cruise that explores Chesapeake landmarks by water, or stop into the National Sailing Hall of Fame to learn about the sport of racing and its champions. On summer evenings, spectators bring folding chairs and cheer the weekly Wednesday night sailboat races just offshore. The thrill of seeing the competitors cross the finish line, spinnakers flying, might just convince you to try it for yourself.
If that's the case, you can book passage on the Schooner Woodwind, a classic, 74-foot sailing vessel that offers low-key cruises on the bay. The Woodwind lets passengers hoist the sails, take the wheel or just relax on daytime and sunset trips. If you're traveling with kids, mini-buccaneers can take to the high seas in an adventure created just for them. Aboard the brig Sea Gypsy, Chesapeake Pirates roll out a giddy nautical romp for youngsters that includes dress-ups, a sea-faring treasure hunt and a water cannon battle under the Jolly Roger.
On a sunny summer afternoon, few activities beat exploring the harbor under your own power. At Annapolis Canoe & Kayak in Eastport, you can rent a kayak, canoe or stand-up paddleboard for an up-close look at the marine scene. Another means of transport, less strenuous and certainly drier, is to hop aboard an Annapolis Water Taxi. The perky little vessels embark from City Dock and crisscross the water, transferring passengers back and forth across Back Creek and upper Spa Creek. They're often hailed by boaters moored in the harbors for a ride into town—so you might sneak a peek at a yacht en route to your destination.
Each October, man-made marine phenomena transform the town. The Annapolis Sailboat Show and Annapolis Powerboat Show, billed as the nation's oldest and largest, are back-to-back boat bazaars drawing throngs of sea dogs and city slickers alike. A network of floating piers around City Dock accommodates more than 200 dazzling new models of craft, and 300 tents are stuffed with lures for buyers and dreamers. In mid-December, the holidays kick off with the Eastport Parade of Lights, when dozens of boats deck their decks in glowing strands (and crews long for those winter socks they tossed in March).
Walking the Colonial Capital
Because Annapolis never industrialized—Baltimore, with its deeper harbor, seized that role—much of its exquisite 18th-century architecture survived. Thanks to a vigilant historic commission, the city's downtown is filled with beautifully preserved blocks that beg to be explored on foot. But be warned: The colonial proportions that give the city its charm also make driving (and parking) challenging, so it's best to leave your car at one of the public garages.
Crowning the gentle hill above the harbor is the handsome State House, the oldest in continuous legislative use in the United States. Visitors can walk its marble corridors to see where George Washington renounced his commission as commander in chief of the Continental Army and Congress later ratified the Treaty of Paris, which ended the Revolutionary War. (The nearby Treaty of Paris Tavern, built in 1776 and named for the event, is a fine place to raise a glass to our forefathers.)
Fanning out from the State House dome are the red-bricked streets and alleys of the Historic District, where 18th-century celebrities like Washington and the Marquis de Lafayette once made their way to resplendent homes for an elegant dinner or a vigorous debate. Along the tree-lined blocks of the Historic District—or in front of handsomely restored mansions like the William Paca House or the Hammond-Harwood House—you'll see costumed guides leading the city's popular walking tours. Dressed in period attire, they share their love of Annapolis and its history with thousands of visitors a year. At the bottom of Main Street, in front of Market House, you'll see a memorial to Alex Haley, the author of Roots, at the water's edge. His enslaved ancestor, Kunte Kinte, came from Gambia to this very dock in chains in 1767.
In addition to the Historic District, neighborhoods like Maryland Avenue and West Street are full of options for shopping and discovery. The self-declared Maritime Republic of Eastport, just across the Spa Creek Bridge, has a more residential vibe. Once a working-class neighborhood for cannery workers and boatyard hands, its modest churches and cottages now nestle amid million-dollar mansions.
Navy Blue, Through and Through
The United States Naval Academy has an outsized influence, as you'd expect from the place where the nation's future military officers and leaders have been educated since 1845. “The Yard” exudes a palpable sense of tradition, populated by razor-trim midshipmen in dashing attire. Admire its beaux-arts architecture, especially the monumental chapel with its Tiffany windows. It's the venue of choice for naval weddings and the site of an ornate crypt housing the remains of John Paul Jones, father of the American Navy.
On weekdays at noon during the academic year, don't miss the daily formation of the 4,400-member brigade in front of Bancroft Hall, when the mids march into place with military precision. At the USNA Visitors Center, you can take in a free, 13-minute film that salutes the storied history of the Academy and its graduates, while the USNA Museum displays treasures and talismans related to the country's naval history, as well as an extensive model ship collection. (As you exit the Visitors Center's gift shop, don't forget to rub Bill the goat, the bronzed Navy mascot, for good luck.) To enter Academy grounds, visitors 18 and older must present a valid government ID and pass through a security check.
Even non-sports fans bleed blue and gold for Navy football. The parade of midshipmen through town to the stadium, and their traditional pushups under the goal posts, are nearly as big a draw as the tailgate parties in the parking lot. The pinnacle of the season is the mids' annual matchup with arch-rival Army, when the 127-year interservice rivalry reaches a crescendo and “Beat Army” banners proliferate across town. Afterward, fans head out to cheer the victory or drown their sorrows. With dozens of dining establishments in town, they have plenty of choices.
Crab Cakes and More
Hungry? Main Street, which connects the harbor to Church Circle, offers seafood at historic Middleton's Tavern, sushi at Joss, margaritas at Vida Taco Bar, French fare at the cozy Café Normandie and locally sourced American fare at Preserve, named as one of the region's top restaurants. West Street, the hub of the city's Arts District, is home to Rams Head Tavern, a microbrewery and concert venue that showcases big-name musicians in an intimate setting. Try nearby Tsumani for Asian fusion and the tiny Sailor's Oyster Bar for bivalves. The Light House Bistro, a go-to spot for coffee, lunch or dinner, has a special place in locals' hearts: It's a visionary social venture operated by the city's shelter for the homeless to provide culinary training and job opportunities to its clients.
Every Annapolitan has a go-to pub: McGarvey's, a City Dock mainstay, is a convivial saloon that's heard more than a few seafaring yarns. In Eastport, a favorite hole-in-the-wall is Davis Pub, where you can follow the locals' lead and order a Dark 'n' Stormy, the sailors' favorite.
The debate over who serves the best crabs (and crabcakes) in town is perennial. It's safe to say that there are dozens of worthy contenders—and plenty of options for oysters, too. Cantler's Riverside Inn, a 10-minute drive from downtown, gets lots of love as one of the region's best crab houses. It's a fun, noisy, family-friendly place where diners dig into fresh steamed “jimmys” dumped directly onto brown paper at shared communal tables. For a more upscale experience—and what might be the city's best cream of crab soup—try Carroll's Creek Restaurant, which serves seafood specialties against the backdrop of Spa Creek and the State House.
Oysters powered the Annapolis economy during the 19th century, when bay watermen and canneries delivered them to the Eastern Seaboard and beyond. Though the Chesapeake's legendary reefs were eventually depleted, those heady days of plentiful harvests are celebrated at the Annapolis Maritime Museum. Housed on Back Creek in a former oyster-packing plant, the museum explains the ecology of the Chesapeake and the city's heyday as a seafood supplier. It features an oyster aquarium, a locally-built workboat and the chance to dip a toe at one of Annapolis's only public beaches.
If you're interested in visiting an authentic Chesapeake lighthouse, the U.S. Lighthouse Society can throw you a line. It runs summer cruises from the Maritime Museum to the beacon at Thomas Point, just south of the city. The octagonal landmark was constructed in 1875 and is still functional, though now fully automated. To explore the former keeper's quarters, you'll need to reserve well ahead, board a small boat for the 30-minute trip and climb a steep ladder, but the 360-degree view of the bay—and the chance to experience the romantic remoteness of the keeper's life—is worth the effort. The Harbor Queen tours also offer a lighthouse trip from City Dock that circles the structure.
The bay defines Maryland's capital city, and the water is where any trip to the region should begin and end. By the seawall at the Naval Academy, on a quiet creek or aboard a river cruise, the appeal of the wind, tide and wide horizon is just as potent today as it's been for millennia. No wonder that visitors return again and again: Annapolis is a fine place to drop anchor.
Carol Denny, former editor of What's Up Annapolis magazine, writes about travel and the environment from her home on the Severn River.
Where to Stay
Yes, George Washington slept in Annapolis—he visited many times—but no, you can't bunk in his bed. For the next best thing, book a stay at the Historic Inns of Annapolis, three downtown boutique properties that offer an authentic 18th-century experience with 21st-century amenities. The venerable Maryland Inn, Governor Calvert House and Robert Johnson House put you in the heart of town and offer Wi-Fi and valet parking.
If nothing but a bay view will do, try the Annapolis Waterfront Hotel on Compromise Street, where you can admire the harbor as well as a fine vista of the Naval Academy. Uptown on West Street, choose from the Loews Annapolis Hotel or O'Callaghan's Hotel, convenient to restaurants and shops and an easy walk to Main Street.