ANNAPOLIS is an ideal place to visit with children - especially those who love water and boats. The historic downtown is compact and walkable, and, if edification is what you're after, there is plenty of history: the Puritans settled in the area in 1649; George Washington resigned his commission as commander in chief there; the Treaty of Paris ending the Revolutionary War was ratified by the Continental Congress there; and the United States Naval Academy was founded there in 1845. But there is also lots of pure here-and-now pleasure.
The focal point of the historic district is City Dock, nicknamed Ego Alley for the show-off boaters who come to one-up each other. Watercraft of all kinds are on display during the spring-through-fall boating season - from the latest in testosterone-driven powerboats to a restored traditional Chesapeake Bay skipjack to schooners and small sailboats. The fall is one of the most pleasant times to take a boat ride around Annapolis's various creeks and coves, to listen to sea chanteys sung by musicians in historic dress, or to feed the brazen ducks. And if you visit soon, you can join the crowds attending two boat shows: the United States Sailboat Show, Oct. 6 to 10, and the United States Powerboat Show, Oct. 13 to 16. Information: (410) 268-8828; on the Web at www.usboat.com.
BY SEA There are lots of ways to get out on the water. A glance at Annapolis's excellent Web site (www.visit-annapolis.org) will fill you in on some reservations-required possibilities that you won't see just walking down City Dock.
Young children might find that a simple water taxi ride fits the bill perfectly. The taxis are so small and ride so low in the water that a child really gets the feeling of being at sea. You can find a water taxi on City Dock, or call (410) 263-0033 (prices range from $2 to $4 a person depending on distance traveled).
For a more personalized tour, try Capt. Rick Brown's Annapolis by Boat. Captain Brown will tell you as much or as little as you want to know about Annapolis's seagoing history; (443) 994-2424; on the Web at www.annapolisbyboat.com; $30 a person. He may even let little ones sit up in the high seat next to him for a spell.
Pirate Adventures on the Chesapeake is a thrill for any child who is 4 to 8 years old and is going through a pirate phase. This 90-minute-ride aboard the Sea Gypsy starts off with face-painting and instruction in pirate lingo (Repeat after me: Shiver me timbers! Walk the plank!) and continues through a search for treasure and a fabulous water assault on an enemy pirate; (410) 263-0002; on the Web at www.chesapeakepirates.com; $17 ages 3 and up, $8.50 for children under 3.
One of the best low-key boating options is a couple of miles out of town at Quiet Waters Park, a lovely 340-acre preserve on the South River. There are places to picnic, six miles of paved trails for biking or walking and, best of all, kayaks (both solo and tandem), canoes, and pedal boats for rent, until mid-October. For boat rentals call (410) 267-8742; prices range from $10 for a half-hour in a pedal boat up to $17 an hour for canoes and kayaks.
BY LAND For a small city, Annapolis is packed with historic architecture, and many of the houses lining the cobbled streets bear explanatory plaques. A leisurely amble might begin on the grounds of the Naval Academy. The academy's year is punctuated with time-honored traditions and obscure rituals: before exams, pennies and notes are left with the statue of the Indian warrior Tecumseh in front of Bancroft Hall, and the hat toss at graduation is renowned. Guided walking tours are available, although children may do better with an unstructured walk around the grounds. Don't miss the two cannons in front of Bancroft Hall, one sporting a suitably menacing gorgon's head spewing fire. The Naval Academy Museum in Preble Hall, with its meticulously detailed models of English and American warships. is another high point. The academy's Web site, www.usna.edu, lists events.
A stop at the William Paca House and Garden is an unexpectedly good idea if you're with children. Skip the fusty antiques inside and head outdoors. Although the parterres may seem intimidatingly manicured, no one bothers a running child, and it's a great place to let off steam. A small bridge at the back of the property leads to a tall "summer house," where children can mount the stairs and survey the scene far below; 186 Prince George Street; (410) 267-7619; www.annapolis.org, $8, $5 for children 6 to 17, under 6 free. Continue across the Spa Creek Bridge to the neighborhood of Eastport, historically a down-at-the-heels area that was the center of the boat-building trade through the mid-20th century. Now Eastport is home to more burnished restaurants than scruffy boatyards, but it's still an interesting walk, and the view of the bay from the bridge can't be beat.
At the Annapolis Maritime Museum's Captain Herbie Sadler Park, two traditional Chesapeake Bay workboats, the Little Hess and the Miss Lonesome, are on display. The museum's renovation of the old McNasby Oyster Company building is scheduled to be finished early next year (parts of it will be open to visitors this month); 723 Second Street; (410) 295-0104; on the Web at www.annapolismaritimemuseum.org.
DOWNTIME Hard Bean Coffee and Booksellers, near City Dock, is a perfect sanctuary for tired parents and youngsters: it has a good children's section, coffee for adults and sweet treats for kids. The excellent Carlson's doughnuts (90 cents) are locally made and come in glazed, jelly and other varieties; 36 Market Space; (410) 263-8770.
Just around the corner, the Waterfront Warehouse is a restored example of the small 18th- and 19th-century warehouses that were once clustered near the waterfront. Inside is a model of the 18th-century city; in the adjoining yard is a tobacco prise, used to press tobacco leaves in the days when tobacco was a major commodity here; 4 Pinkney Street; (800) 603-4020.
WHERE TO EAT The celebrated crab houses - Jimmy Cantler's Riverside Inn and Mike's Bar and Crab House - have fans among tourists and residents, but for a local angle, try Magothy Seafood, just minutes from the historic district by car, at 700 Mill Creek Road, in nearby Arnold (410) 647-5793. Although the hard-drinking crowd at the bar might lead you to believe this is no place for children, don't be misled. At the outdoor picnic tables overlooking the sleepy Magothy River you can enjoy crabs, oysters, crab cakes and pink lemonade for the children; $25 will buy you a feast. And then there is the built-in entertainment: the boats tied up at the restaurant's doorstep are owned by friendly folks who don't mind a wandering child and parent gawking at their craft.
For picnic fare, visit the Big Cheese in the historic district, 47 Randall Street; (410) 263-6915, for great breads, chatty owners, good prosciutto and soprasetta (sandwiches from $5.25 to $9.35). In Eastport, the Boatyard Bar and Grill deftly manages to span the territory between raucous sailors' hangout and civilized brunch spot, while being extremely welcoming to children. You can munch steamed shrimp or garlic mussels with your beer or start your day with sausage gravy and biscuits or buttermilk pancakes; Severn Avenue and Fourth Street; (410) 216-6206; dinner averages about $20 a person.
WHERE TO STAY Although Annapolis is bursting with lovely restored bed-and-breakfasts, many of them don't accept young children. A sure - if more prosaic - bet is the Marriott Waterfront hotel, near City Dock. The hotel's restaurant and bar, Pusser's Landing, has outdoor seating with a great view of the boats and Ego Alley doings. Rooms range from $289 to $549; 80 Compromise Street; (410) 268-7555. In keeping with the strong Irish presence in Annapolis, O'Callaghan Hotels, an Irish chain, has opened a branch at 174 West Street, a few blocks from the historic district. Rooms from $109 to $290; (410) 263-7700.