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What to do in Annapolis

Surrounded by water on three sides, Maryland's state capital is a cosmopolitan city with small-town charm. In the waterfront downtown area, the red-brick streets and Colonial-era buildings give it the feeling of a film set. Kids will love the beaches, boats and exploring the United States Naval Academy (USNA).

Annapolis, Maryland
Bob Peterson Photography

Where to go in Annapolis

To orient yourselves, start your vacation with a Discover Annapolis Trolley Tour. You'll pass some of the city's biggest sites, including the dome-topped Maryland State House, City Dock and St. John's, the country's oldest college. Get to the United States Naval Academy (USNA) in time to watch the pomp and pageantry of the midshipmen's noon formation. To the tune of horns and the beat of drums, the student body lines up by company before marching to the dining hall.

Downtown Annapolis, Maryland
VisitAnnapolis.org

Guests can also take a walking tour of campus, visit the U.S. Naval Academy Museum and eat lunch at the casual Drydock Restaurant (known for its pizza) or at The Alley, a restaurant in the former bowling lanes of the Naval Academy Club.

United States Naval Academy, Annapolis, Maryland
USNA

On the west side of the Chesapeake Bay Bridge, Sandy Point State Park has hiking trails, boat rentals and a swimmable beach. Don't leave Annapolis without exploring the area from the water. Younger kids will love the shiver-me-timbers stunts on a trip with Pirate Adventures on the Chesapeake (they'll search for treasure and fire water cannons). Too old for the theme thing? The sleek, stylish Schooner Woodwind offers relaxed trips around the bay on a two-masted sailboat.

Pirate Adventures, Annapolis, Maryland
VisitAnnapolis.org

Where to stay in Annapolis

The Annapolis Waterfront Hotel is currently the only lodging in the city that's directly on the harbor; it overlooks the slender waterway Ego Alley, known as a spot for people- and boat-watching. Rooms overlook the bay or the charming cityscape, and are in done in a crisp, navy-and-white palette that reflects the surroundings. Loews Annapolis is within easy walking distance of the State House. Rooms feel fresh and modern, and the hotel offers kids gifts at check-in: activity books for the younger ones and music download gift cards for tweens and teens. Guests can raid the lending library, which has board games and handheld game consoles, as well as the "kids' closet," which is filled with toys, car seats, strollers, nightlights, and portable DVD players. Standard rooms have either one king bed or two doubles (not queens), but the hotel lends cribs and cots if you need extra sleeping space.

Cantler's Riverside Inn, Steamed Crabs, Annapolis, Maryland
VisitAnnapolis.org

Where to eat in Annapolis

Celebrities, politicians, locals and tourists pack the booths at Chick and Ruth's Delly, an Annapolis institution where the staff recites the Pledge of Allegiance every morning. Breakfast is served all day and the crab cakes, which the restaurant ships nationwide, are incredibly popular. It's worth waiting for an outdoor table overlooking Mill Creek at Cantler's Riverside Inn, in a quiet residential area outside downtown. The restaurant specializes in crab, so be sure to order some steamed, mixed into a crab cake or blended into dip or soup. If the wait is long, the parking lot has a dedicated bar area and kids can pass the time watching boats come and go.

Looking for more of the best vacations with kids? Check out TODAY's Family Travel Guide.

Lexi Dwyer contributed.