We found the perfect fall weekend destination—and a 14-year-old sailor who agreed to chart an exciting course for visiting families
OUR GUIDE Scott
GUIDE QUALIFICATIONS Spends almost as much time on the water as on dry land.
FAVORITE FOOD Steamed crabs—can put away a half-dozen in one go.
BEST SCHOOL SUBJECT Civics, because "this town is full of politicians."
TALENT Sailing Optis (solo boats for kids)—fast!
COLLECTION Triangular yacht-club flags, known as burgees—souvenirs from his regattas.
Quick: What's the capital of Maryland?If you answered "Annapolis," give yourself a gold star, just like those officers wear at the U.S. Naval Academy downtown. Nestled between two rivers on giant Chesapeake Bay (and not far from Baltimore and D.C.), Annapolis is celebrated for its historic center—George Washington slept here, for real!—and its maritime mania. A thicket of masts is visible from practically every vantage on Main Street, and kids here can rattle off the stats of America's Cup stars as readily as other kids can spout baseball trivia. One such local, Scot—a competitive sailor who lives with his mom, dad, and younger sisters Darby, 11, and Stephanie, 7, on a creek off the South River—showed us the Naptown ropes.
THE HIGHS AND THE LOWS, IN 25 WORDS
It's laid-back here, and you can walk or bike most places—or take a water taxi. Downtown is fun, but the traffic gets to me!
THE CENTER OF THE ACTION
Ego Alley, right at the bottom of Main Street, is the slip of water at City Dock. It's where people drive up in their boats to show off. There's a statue of Alex Haley there, because in the book Roots, Annapolis is where Kunta Kinte arrives. Storm Bros. Ice Cream Factory [130 Dock St.; 410/263-3376; stormbros.com] is just across the street, so you can get a cone and watch the boat parade.
OTHER ESSENTIAL STOPS DOWNTOWN
The best spot for breakfast or lunch is Chick & Ruth's Delly [165 Main St.; 410/269-6737; lunch for four $30]; they recite the Pledge of Allegiance every morning when they open, and all the sandwiches are named for famous politicians. Sometimes the owner does magic tricks. You also have to go to Fawcett's [110 Compromise St.; 800/456-9151], the biggest boating-supply store in town. I love to look around at all the stuff. You can get ship models there, and rope bracelets—did you know that they were invented by sailors who used to use them as sweatbands?Too bad my karate teacher made me cut mine off.
AT THE NAVAL ACADEMY
People who come to town always like to check out the campus—it's got big old buildings and is surrounded on three sides by water. Right now an F-86 Sabre is parked in front of the Observatory. But if you ask me, the best thing about the Naval Academy is the Fawcett's [800/874-6289; navysports.cstv.com]. At the start, there's always a huge flyover, with Navy SEAL parachuters dropping down onto the field. The Navy mascots are goats, all named Bill, and when they bring them out everyone goes crazy. Anytime Navy scores, midshipmen have to race down and do push-ups. It's wild!
IF YOU WANT TO TOUR AN OLD HOUSE
The William Paca House [186 Prince George St.; 800/603-4020; annapolis.org] is the biggest, fanciest one around. Paca signed the Declaration of Independence. Out in back there are gardens, and a pond with a bridge.
FOR HALLOWEEN THRILLS
Take a ghost tour of Annapolis [92 Maryland Ave.; 410/216-6005; ghostsofannapolis.com]. The guides carry lanterns and will tell you about the guy who was crushed to death inside the State House dome!
TO ESCAPE THE TOURISTS
Go to Eastport—it's the neighborhood just over the Spa Creek Bridge from downtown, and is full of marinas and good biking streets. Every fall there's a big tug-of-war across the creek between Eastporters and the people who live in the historic district [This year's contest is November 4; for details, see themre.org]. It's over in about a minute. Boatyard Bar & Grill [Severn Ave. and Fourth St.; 410/216-6206; dinner for four $60] is where the sailors hang out. It has awesome fish-and-chips and crab cakes, and there are old photos everywhere. Sail magazine voted it one of the best sailing bars in the world.
ON THE MENU IN ANNAPOLIS (AND ALMOST NO PLACE ELSE)
Steamed blue crabs from Chesapeake Bay. They're covered in Old Bay Seasoning. My favorite crab house is Mike's [3030 Riva Rd.; 410/956-2784; dinner for four $100], on the South River. You can sit on the deck, and the waiter will dump a big pile of crabs in the middle of the table. Anyone there can show you how to pick them apart. I think the best-tasting part is the back fin.
THE EASIEST WAY TO GET OUT ON THE WATER
Catch a water taxi [watermarkjourney.com] from City Dock. The taxi captains know all kinds of local stories—my father always says that when he retires from commercial real estate, he wants to be one of them. It's also cool to sail on the Woodwind [410/263-7837; schoonerwoodwind.com; $35 adults, $20 children, for a two-hour ride]. It's a wooden schooner that cruises the bay. Scenes from The Wedding Crashers were filmed on it.
BUT IF YOU REALLY WANT TO SAIL...
Charter a boat from South River Boat Rentals [410/956-9729; annapolisboatrental.com; half-day from $140; overnight $500] and drop anchor in Harness Creek, off the South River. It's good for swimming—just watch out for sea nettles—they sting. Dock for the night in St. Michaels. It doesn't take long to get there, but you feel really far away. —As told to Meeghan Truelove
From the Historic Annapolis Foundation (800/603-4020; $5)
From the Historic Annapolis Foundation ($5)
The Local Spice
At supermarkets (mccormick.com; $3.30)
From Fawcett (800/456-9151; $24)
Travel tips from Scott's mom and dad, Carolyn and David
WHEN TO COME
Summer is the most popular time, but fall is ideal—less crowded, and the foliage is gorgeous.
HOW TO GET HERE
The nearest airport is Baltimore's BWI, a 25-minute drive from Annapolis. Lots of visitors day-trip from Washington D.C., about 45 minutes away by car.
WHERE TO STAY
Marriott Annapolis Waterfront
The best choice for families—located downtown, right on the water. The lobby is filled with ship models. 80 Compromise St.; 800/393-0047; annapolismarriott.com; doubles from $299.Maryland Inn
This 18th-century hotel near the State House is where the Treaty of Paris, which ended the Revolutionary War, was drafted. 16 Church Circle; 410/263-2641; annapolisinns.com; doubles from $249.
A FALL DRIVE
Head south on Route 2 for 20 minutes, to 214 (W. Central Ave.). Homestead Gardens (743 W. Central Ave.; Davidson; 800/300-5631; homesteadgardens.com) has llamas, pumpkin picking, and sometimes even live reggae.