1. Get the touristy stuff out of the way.
Aside from subway commuters, chaos is at a minimum in the morning, so do your heavy tourist attractions (if you must) then. Head up to Times Square (Broadway & 42nd St.) which has been converted into a pedestrian promenade. Give yourself twenty minutes to take in the Broadway marquees, news tickers, neon lights, and Naked Cowboy. Everything really looks just like it does in the movies! Now, get out of there. Walk east two blocks towards Bryant Park for a photo op between the lions at the New York Public Library (Fifth Ave. & 42nd St.).
Stroll up Fifth Avenue, past Rockefeller Center (on your left), Saks Fifth Avenue (on your right), designer boutiques (like Cartier, Tiffany's, Bergdorf Goodman), FAO Schwarz toy emporium, and the 24-hour Apple technology mecca. You'll hit the southeast entrance of Central Park (right across from the Plaza for high tea). Along the paths you'll find ponds, lakes, ice-skating rinks, swing sets, a resevoir path, marionette theater, and lots of park benches for people-watching (one of the greatest pastimes of all).
For fancy window-shopping, walk east to Madison Avenue and head uptown. You'll find all the stores they talk about in hip hop songs: Armani, Versace, Prada, Valentino, Yves Saint Laurent. For a taste of vintage New York, sit at the counter at Viand (Madison Ave & 61st Street), a classic diner fixture serving excellent coffee and hefty turkey sandwiches to shop girls and suits. Or, for something trendier, dine at Fred's, the ninth floor cafe at boutique department store Barneys New York.
2. Socialize oustide.
- Union Square Greenmarket: where chefs catch up with farmers, and locals wait in line for farm fresh eggs, produce, meat, and flowers.
- New Amsterdam Market: small-batch artisans showcase baked goods, seafood, ice cream, and wine down by the South Street Seaport.
- Brooklyn Flea: not quite a traditional flea market, but more like a highly curated selection of vintage stalls, collectors, and food stations celebrating Brooklyn's dining and shopping scene.
- Red Hook Ball Fields: A soccer field surrounded by food carts dishing out gargantuan portions of Central American street food.
- Riverside Park: A lavishly planted strip of gardens and promenade (for walking, biking, skating) close to the Hudson River.
- High Line: An old elevated railway on Manhattan's west side is now a strollable walkway soaring high above the streets of Chelsea.
3. Take advantage of the art.
- Museum Mile is located on the east side of Central Park, along Fifth Avenue, from 70th-105th Streets.
- You can get a good dose of grand New York living at The Frick, a former private home and collection.
- Beautiful behemoth The Metropolitan Museum of Art is pay as you wish.
- Neue Galerie is a gorgeous German/Austrian art museum with Cafe Sabarsky, a picturesque Viennese-inspired eatery.
- The Guggenheim is architect Frank Lloyd Wright's torqued museum marvel.
- If you're interested in design history, try the Cooper-Hewitt .
- El Museo del Barrio explores the contemporary visual arts of the Caribbean and Latin America.
- And while the American Museum of Natural History is not technically on Museum Mile, it's just a nice stroll through Central Park. We're particularly excited about Rose Center for Earth and Space.
4. Eat an iconic dish at an iconic restaurant.
- The Oyster Bar pan roast: The Grand Central Oyster Bar
- Pastrami sandwich on rye: Second Avenue Deli, Katz's Delicatessen
- Burger: Peter Luger
- Steak and Baked Alaska: Delmonico's
- Steak frites: Balthazar
- Bagel, schmear, lox: Russ & Daughters, Barney Greengrass
- Pizza slice: there are serious contenders for best old-school slice. Ask a local, or start with Joe's, Spumoni Gardens, or Di Fara
5. Taste a perfectly mixed cocktail at a famous bar.
- King Cole Bar at the St. Regis Hotel
- Bemelman's Bar at the Carlyle Hotel
- Campbell Apartment
- Milk & Honey
6. See something live.
- BAM, for the unusual, spectacular, and avant garde.
- Lincoln Center, so you can get dressed up and take a picture near the fountain.
- Joyce, to see downtown dancers up close and in action.
- The Public Theater, to get a peek at plays before they hit Broadway.
- Bowery Ballroom, for the best indie rock acts about to blow up.
- Le Poisson Rouge, to hear the best music happening in all corners of the world.
- Smalls Jazz Club, for the quintessential late-night dive.
- HERE Arts, for daring new hybrid performances.
- The Kitchen, to experience the experimental firsthand.
7. Have an incredible meal after midnight.
- Blue Ribbon Brasserie: Sets the standard for late-night white-tablecloth service.
- 'Inoteca: Stellar Italian wine list accessible until 4 a.m.
- The Spotted Pig: Fancy tavern food.
- Momofuku Ssäm Bar: Pork belly at 2 a.m.
- Fatty Crab: Spicy small plates inspired by Malaysian cuisine.
- Sushi Seki: Midnight omakase.
- Kunjip: 24-hour Koreatown.
8. Stay out late.
Underground parties reject the bland club scene and embrace live music, world-class djs, performace artists, empty warehouses, forgotten lofts, outdoor lots, and boat basins. The crowd follows suit. Nonsense NYC is an email list that relays information on hard-to-catch parties and off-beat cultural events. Other Music often sells tickets to some of the under-the-radar music happenings.
- Todd P
- Mister Saturday Night
- Shanghai Mermaid
- The Danger
- Sound Noir
- Wolf + Lamb
9. Have an only-in-New-York moment.
- Trapeze School New York: Soar outdoors, high above the Hudson.
- Steve Cohen's Chamber Magic: Victorian slight of hand in a fancy hotel suite.
- KGB Reading Series: Literary salon in a Communist-themed East Village dive bar.
- Coney Island Circus Sideshow: Freaks, wonders, and human curiosities.
- Little Odessa: Bizarre Russian time-warp enclave (vodka, peroxide hair, tracksuits) on Brighton Beach.