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 (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 (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
2. Socialize oustide.
- : where chefs catch up with farmers, and locals wait in line for farm fresh eggs, produce, meat, and flowers.
- : small-batch artisans showcase baked goods, seafood, ice cream, and wine down by the South Street Seaport.
- : 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.
- : A soccer field surrounded by food carts dishing out gargantuan portions of Central American street food.
- : A lavishly planted strip of gardens and promenade (for walking, biking, skating) close to the Hudson River.
- : 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 , a former private home and collection.
- Beautiful behemoth is pay as you wish.
- is a gorgeous German/Austrian art museum with Cafe Sabarsky, a picturesque Viennese-inspired eatery.
- is architect Frank Lloyd Wright's torqued museum marvel.- If you're interested in design history, try the .
- explores the contemporary visual arts of the Caribbean and Latin America.
- And while the is not technically on Museum Mile, it's just a nice stroll through Central Park. We're particularly excited about .
4. Eat an iconic dish at an iconic restaurant.
- The Oyster Bar pan roast:
- Pastrami sandwich on rye: ,
- Steak and Baked Alaska:
- Steak frites:
- Bagel, schmear, lox: ,
- Pizza slice: there are serious contenders for best old-school slice. Ask a local, or start with , , or
5. Taste a perfectly mixed cocktail at a famous bar.
- at the St. Regis Hotel
- at the Carlyle Hotel
6. See something live.
- , for the unusual, spectacular, and avant garde.
- , so you can get dressed up and take a picture near the fountain.
- , to see downtown dancers up close and in action.
- , to get a peek at plays before they hit Broadway.
- , for the best indie rock acts about to blow up.
- , to hear the best music happening in all corners of the world.
- , for the quintessential late-night dive.
- , for daring new hybrid performances.
- , to experience the experimental firsthand.
7. Have an incredible meal after midnight.
- : Sets the standard for late-night white-tablecloth service.
- : Stellar Italian wine list accessible until 4 a.m.
- : Fancy tavern food.
- : Pork belly at 2 a.m.
- : Spicy small plates inspired by Malaysian cuisine.
- : Midnight omakase.
- : 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. is an email list that relays information on hard-to-catch parties and off-beat cultural events. often sells tickets to some of the under-the-radar music happenings.
9. Have an only-in-New-York moment.
- : Soar outdoors, high above the Hudson.
- : Victorian slight of hand in a fancy hotel suite.
- : Literary salon in a Communist-themed East Village dive bar.
- : Freaks, wonders, and human curiosities.
- : Bizarre Russian time-warp enclave (vodka, peroxide hair, tracksuits) on Brighton Beach.