Day One: Uptown and Midtown
Don’t get us wrong: We love the subway. But it’s tough to get the lay of the land when you’re constantly underground. On your first day, see the town by bus and foot instead.
9 a.m.: Catch a bus and watch the town whiz by. To get your bearings, start at 42nd Street and Eighth Avenue and hop on a Gray Line double-decker bus — the best way to see a lot of the city in a little bit of time. You can choose among 15 routes, but we recommend the Uptown Tour ($44 per adult), which takes you north to Harlem, with stops at Central Park, Lincoln Center, the Upper West Side’s Dakota Apartments, and Fifth Avenue’s Museum Mile.
11:30 a.m.: Bask in the lights of Broadway. The bus tour will end where it began; from there, walk east a block to Broadway and enter Times Square. Enjoy the screaming billboards, the honking cabs, and the Naked Cowboy, and have lunch at the anti–Olive Garden, Bond 45, a delicious, home-style Italian restaurant designed by Tony Award winner John Lee Beatty.
1:30 p.m.: Take a ride on a classic escalator. Stroll down Broadway to 34th Street, home to one of the world’s largest department stores, Macy’s Herald Square. The block-long, Art Deco landmark comes complete with the original wooden escalators from 1902 — the first to be used in an American store. Ride it up to the balcony-level visitor’s desk to get a Visitor Savings Pass, good for 10 percent off.
2:30 p.m.: See the city from on high. Head east on 34th Street to the Empire State Building. Because of the long lines, your journey to the top can stretch as long as two hours. (Which might be as long as it would take on the stairs.) To save time, purchase printable tickets online in advance (Esbnyc.com).
5 p.m.: Hit the stacks. Stroll up Fifth Avenue, past the main branch of the New York Public Library at 42nd Street, unmissable thanks to the pink-marble lions out front. Bryant Park, home to HBO’s great summertime film series, is right behind it. Browse through books and magazines at the outdoor Reading Room, then sip cocktails on the patio (or heated tent in winter) at the Bryant Park Grill. Your thirst quenched, continue on to Rockefeller Center, making a left on 49th Street. The sprawling complex includes the GE Building (a.k.a. 30 Rock, home to NBC) and, in the winter, the iconic Christmas tree and ice rink.
7 p.m.: Get spritzed at Saks. Across the street, gaze at Saks Fifth Avenue’s famously elaborate window displays before entering the legendary ten-floor department store, full of eager perfume spritzers and in-store boutiques of designers like Chanel, Escada, and Louis Vuitton.
8 p.m.: End the day at a New York classic. Get drinks and dinner at Grand Central Terminal’s Campbell Apartment—a ’20s railroad tycoon’s office turned retro-chic bar. Then pick from one of more than 20 different types of oysters at the landmark Oyster Bar & Restaurant.
Day Two: Downtown and Brooklyn
To truly understand where New York’s been (and where it’s going), head below 14th Street.
8:30 a.m.: Grab some grub at the Greenmarket. Start with breakfast at Union Square’s Coffee Shop, a 23-hour-a-day joint known for its Brazilian-meets-diner fare and slightly aloof model-waiters. If you’re here on a Monday, Wednesday, Friday, or Saturday, do a post-meal loop around the Union Square Greenmarket, where even the city’s best chefs go to load up on locally grown produce.
9:15 a.m.: Pay a visit to America’s leading lady. Take the 4 or 5 train down to Battery Park to catch the 10 a.m. Statue Cruises ferry to the Statue of Liberty. (Tickets can be purchased in advance at statuecruises.com.)You’ll dock at Liberty Island 15 minutes later. Access to the lobby, museum, and pedestal observation deck is by pass only; these can be reserved ahead of time at statuereservations.comor by calling 877-523-9849.
Noon: Pay your respects at a living memorial. Walk up Trinity Place to the former World Trade Center site to visit the 9/11 Memorial. (Be sure to reserve visitor passes ahead of time at visit.911memorial.org.) Then cross the street to Saint Paul’s Chapel. Port Authority did away with the flowers, letters, and hand-painted banners, but memorialized pews still bear the scuff marks of the 9/11 rescue workers who rested, ate, and slept there.
1 p.m.: Cross the East River for lunch. Hop on the A or C subway and take it to High Street in Brooklyn, walking west toward the river, and grab lunch at Grimaldi’s Pizzeria — arguably one of New York’s best pies. (It’s cash only, though there is an ATM on site.) Afterward, amble a block toward the water to Fulton Ferry Landing, site of George Washington’s famous retreat during the Battle of Brooklyn. Indulge your sweet tooth at Brooklyn Ice Cream Factory, located in a red-and-white ’20s fireboat house, where the dark-chocolate hot fudge is crafted by Karen McGrath, pastry chef at top-rated River Café next door. Then double back up the street to the pedestrian entrance to the Brooklyn Bridge, and walk back across the river, enjoying sweeping views of the city skyline.
4 p.m.: Blast back to the seafaring days. Back in Manhattan, it’s a five-minute walk to cobblestoned South Street Seaport, a once-thriving maritime district where the lightship Ambrose, the four-mast Peking, circa 1911, and the wrought-iron Wavertree — all part of the South Street Seaport museum — are still docked.
5:30 p.m.: Peruse suspiciously cheap goods. Take an uptown 6 train to Chinatown for an evening of discount browsing along Canal Street, where you can haggle for knockoff sunglasses, perfume, and leather goods (think fake Prada handbags).
8 p.m.: Gobble, then ogle at a local landmark. Dine downtown at Vic’s or a newer star, like old-world bistro Virginia’s, where the modern-eclectic menu includes chocolate-beet cake and a warm Morcilla salad. After dinner, stroll across town through winding Greenwich Village streets to the Meatpacking District. Pop into the retro-chic Maritime Hotel, then keep your eyes peeled for celebs at the ultrasceney, tropical-themed rooftop lounge, The Cabanas.
Day Three: Midtown
You’ve worked your calves, now work your mind with a tour through some important cultural sites.
10 a.m.: Meander through masterpieces. Spend the morning at either the sprawling Metropolitan Museum of Art or the Museum of Modern Art. At the Met, don’t miss the Temple of Dendur, the European paintings, and the views from the rooftop café; at MoMA, visit Warhol’s Campbell’s Soup Cans on the second floor and van Gogh’s The Starry Night on the fifth floor, then wander into the Sculpture Garden, redesigned by Philip Johnson in 1953.
1 p.m.: Gorge yourself like an over-the-top Russian czar. Take a cab from the Met or walk from MoMA to the deliciously kitschy Russian Tea Room at 57th and Seventh, originally opened by members of the Russian Imperial Ballet in the ’20s. Slide into the trademark red leather banquettes and dig into caviar served on silver trays and beef Stroganoff topped with wild mushrooms and red-wine sauce.
3 p.m.: Commune with dinos. Enjoy the American Museum of Natural History, home to the world’s largest collection of vertebrate fossils. Check out the famous dioramas, and chart the history of outer space in the glass-enclosed Rose Center for Earth and Space.
6:30 p.m.: Eat where the actors do. Have a preshow meal at Joe Allen, a Theater District favorite with both showgoers and cast members since 1965. The menu’s as eclectic as the cast of Rent: burgers, steak tartare, and vegetarian stew along with fresh guacamole, tostadas, and toothsome desserts.
8 p.m.: Experience the Great White Way. After purchasing Broadway tickets in advance (click here for tips), join the pre-curtain crowds on the sidewalk, and enjoy the show.
10:30 p.m.: Cap off the night with a cocktail. Wind down with a drink at Blue Fin in the W New York in Times Square.
Day Four: Excursions
1. Located about 50 miles north of New York City, in the picturesque Hudson Valley region, Bear Mountain State Park counters the sidewalk jungle with hiking trails and rugged mountain paths, plus lakes with rentable paddle boats and rowboats. There’s even an outdoor swimming pool and, from November through March, an ice-skating rink. (Once in the park, clearly marked signs will direct you to all of the above.) Take a Short Line bus from Port Authority Bus Terminal on the West Point route; the last bus heads back to New York in the late afternoon on most days, so be sure to check the current schedule.
2. About an hour from midtown (take the D, Q, N, or F train to Stillwell Avenue), Coney Island is still a worthwhile destination. Enjoy the rides at Luna Park (named after the one that burned down in the ’40s), the latest addition to the beach’s amusement-park legacy, or ride the legendary Cyclone roller coaster (built in 1927) or the Wonder Wheel (built in 1920). Also be sure to check out the New York Aquarium or Nathan’s Famous (home of the notorious Fourth of July hot-dog-eating contest).
3. Sitting at the very tip of Long Island’s South Fork about 120 miles from the city, Montauk offers a variety of day-trip diversions. Both kids and adults will get a kick out of seal watching, half-day fishing excursions, or visiting the Montauk Point Lighthouse, not to mention surfing, kayaking, or plain old sunbathing. Take the Long Island Railroad, the Hampton Jitney, or a rental car to reach Montauk.
With reporting by Candace Taylor.
Liberty St. at Greenwich St.
American Museum of Natural History
Central Park W. at 79th St.
Bear Mountain State Park
Palisades Parkway, Bear Mountain, N.Y.
W New York Times Square
1567 Broadway, nr. 47th St.
154 W. 45th St., nr. Seventh Ave.
City Hall Park at Centre St.
Brooklyn Ice Cream Factory
1 Water St., nr. Old Fulton St., Brooklyn
Sixth Ave. at 42nd St.
Bryant Park Grill
25 W. 40th St., nr. Fifth Ave.
15 Vanderbilt Ave., nr. 42nd St.
1000 Surf Ave., at W. 10th St., Brooklyn
1 Ellis Island
Empire State Building
350 Fifth Ave., nr. 34th St.
Grand Central Terminal
Lexington Ave. at 42nd St.
Gray Line Visitors Center
777 Eighth Ave., nr. 47th St.
1 Front St., nr. Old Fulton St., Dumbo
326 W. 46th St., nr. Eighth Ave.
1000 Surf Ave., at W. 10th St.
Macy’s Herald Square
151 W. 34th St., at Broadway
63 W. 16th St., at Ninth Ave.
Metropolitan Museum of Art
1000 Fifth Ave., at 82nd St.
Montauk Point Lighthouse
2000 Montauk Hwy., Montauk, N.Y.
Museum of Modern Art
11 W. 53rd St., nr. Sixth Ave.
1310 Surf Ave., at Stilwell Ave., Brooklyn
New York Aquarium
602 Surf Ave., at W. 8th St., Brooklyn
New York Public Library
476 Fifth Ave., at 41st St.
Russian Tea Room
150 W. 57th St., nr. Sixth Ave.
Saks Fifth Avenue
611 Fifth Ave., at 50th St.
South Street Seaport Museum
12 Fulton St., nr. South St.
St. Paul’s Chapel
209 Broadway, at Fulton St.
Statue of Liberty
1 Liberty Island
Union Square Greenmarket
E. 17th St. at Broadway
31 Great Jones St., nr. Lafayette St.
SEE ALSO: New York on a Budget Lovers’ Itinerary Bus & Boat Tours Top Walking Tours Video: A Stroll Through Central Park Video: An Afternoon at the Met Museum