For an after-school treat, David squires Summer and a friend to Books of Wonder (18 W. 18th St.; 212/989-3270; booksofwonder.net), which shares a high-ceilinged space with a branch of the Cupcake Café—a combo that inspired the bookstore in You've Got Mail.
Yoya (636 Hudson St.; 646/336-6844; yoyashop.com) and sibling Yoyamart (15 Gansevoort St.; 212/242-5511) are ostensibly kids' stores, so why do parents get so excited here?Swoon over European fashions for wee ones at the former; get monkey-devil T-shirts, Japanese toys, and the world's coolest sneakers at the latter.
Hmm…should it be pretzel croissants or caramelized French toast?Whatever else you order at big, bustling City Bakery (3 W. 18th St.; 212/366-1414; thecitybakery.com), get the thick hot chocolate with house-made marshmallows—and check out the kids' play kitchen under the stairs.
Grab a frosted-blue aluminum seat at Pop Burger (58–60 Ninth Ave.; 212/414- 8686; popburger.com), admire the Jean-Michel Basquiat paintings, and place your order. Two mini patties on fresh brioche rolls ($5) come snuggled in a tidy white box.
The Miguel-Strah family plops onto a banquette at El Cocotero (228 W. 18th St.; 212/206-8930; elcocotero.com; dinner for four $66), a festive Venezuelan spot with rice and beans and passion-fruit juice for the kids, grilled-chicken salad for Daddy David and Daddy Barry, tres leches cake for all.
With its white tablecloths and seriously good Tuscan food, Da Umberto (107 W. 17th St.; 212/989-0303; dinner for four $120) is just right for a big night out. "It's where we taught our kids how to eat in a proper place with a napkin in their laps," David says. "Or, I should say, we tried to teach them.…"
At the Union Square Greenmarket (14th to 17th Sts., just east of Broadway; 212/788-7476; cenyc.org; open Mon., Wed., Fri., and Sat.), the granddaddy of the city's beloved farmers' markets, David and the kids graze on free samples of cider, sausages, and pumpkin bread while gathering just-picked apples and pears. Last stop: the playground in the middle of it all.
At Chelsea Market (75 Ninth Ave.; 212/652-2121; chelseamarket.com), a fabulous food hall in a repurposed 1890's Nabisco factory, you can watch the bakers at Amy's Bread, then pick up some of Eleni's Statue of Liberty–shaped cookies.
Started by defectors from the West Village's Magnolia Bakery, the retro-style Billy's Bakery (184 9th Ave.; 212/647-9946; billysbakerynyc.com) tops red-velvet cupcakes with white peaks of cream-cheese frosting.
David, Barry, Zev, and Summer love hopping on the New York Water Taxi (nywatertaxi.com; board at Pier 45, btw. W. 10th and Christopher Sts.), a river-going version of an old checker cab. Zip around the southern tip of Manhattan to DUMBO for a stroll along the Brookyn Heights Promenade, pizza at Grimaldi's, and a cone from the Brooklyn Ice Cream Factory. Then catch a water taxi back.
Hotel Gansevoort (18 Ninth Ave.; 212/206-6700; hotelgansevoort.com; doubles from $635) A happening place just south of Chelsea that lures families with baby toiletries, use of Nintendo Wii consoles, and a rooftop pool. Rooms in the back are quieter.
Four Points by Sheraton (160 W. 25th St.; 212/627-1888; starwoodhotels.com; doubles from $425) A 22-story tower in a prime location—ask for a view of the Empire State Building.