Day 2: Midtown and Downtown
Experience life in Time Square’s fast lane, then take an urban hike across the Brooklyn Bridge.
9 a.m.: Hyperactivate with chocolate-chip pancakes at Ellen’s Stardust, a fifties-themed diner in Times Square where show-tune-belting waitstaff and a circling model train dash any hope you had of sleepwalking through the morning.
10 a.m.: Follow Broadway downtown for a "bright lights, big city" moment. With its blinking marquees and Jumbotron screens, Times Square provides the quintessential New York setting. Duck into the three-story Toys ‘R’ Us, at 44th Street, for a ride on the 60-foot Ferris heel or for a visit to the life-size Barbie House.
11 a.m.: Worship at the chapel of transportation. Walk due east on 42nd Street to Grand Central Terminal. The magnificent constellations on the main concourse’s ceiling are an eyeful; downstairs, you can top it off with a bellyful of cheeseburgers and world-famous cheesecake ($6.50) at Junior’s.
12:30 p.m.: Steal a few moments of quietude. Hop on the 1 train and go downtown to 18th Street for Books of Wonder, an all-children’s bookstore where kids peek at picture books or ransack tween titles. Collectors will be equally entranced by the leather-bound classics and Doctor Dolittle first editions in the old- and rare-books section.
1:30 p.m.: See what’s in season. Grab healthy muffins, fresh-from-the-orchard apples, and Ronnybrook chocolate milk at the bustling Union Square Greenmarket (Mon., Wed., Fri., and Sat.). For heartier grub, slurp some soup ($11 to $14) at the noodle emporium Republic, located on Union Square’s western perimeter.
2 p.m.: Bridge the gap between the boroughs. Catch the 4 or 5 train to Brooklyn Bridge–City Hall, then go for a mile-long walk over one of America's best-known landmarks, the Brooklyn Bridge. (Keep your eyes peeled south for the Statue of Liberty.) Your reward on the other side? All-natural ice cream ($4 for a small cone) and skyline views at Brooklyn Ice Cream Factory at the foot of Water Street.
4 p.m.: Blast back to the age of tall ships. After doubling back to Manhattan (most likely by taking a cab or the A or C train), walk the cobblestones of Fulton Street toward the East River, where the South Street Seaport Museum’s historic ships are docked.
6 p.m.: Make room for macaroni and cheese. Return to Union Square via the 4, 5, or 6 for preshow grub at S'MAC. This kid-friendly restaurant in the East Village lets young ones play it safe with traditional mac 'n' cheese or the comparably experimental mac 'n' shiitakes.
8 p.m.: Feel the rhythm of Stomp. A perennial Off Broadway favorite, this percussion performance piece plays just four blocks south on Second Avenue. Sure, it's been an exhausting day, but the performers' stamina will inspire you to stay awake just a little bit longer. (Children under 5 are not permitted.)