Liberty Island   (Photo: Tema Stauffer)

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 22-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. Circle Line ferry to the Statue of Liberty and Ellis Island. (Tickets can be purchased in advance at Circlelinedowntown.com). You’ll dock at Liberty Island fifteen minutes later. Access to the lobby, museum, and pedestal observation deck is by pass only; these can be reserved ahead of time at Statuereservations.com or by calling 866-782-8834. (Access to the crown is closed.) Free, ranger-guided tours of the grounds are on a first-come, first-served basis, and self-guided audio tours can be picked up for $6.

11 a.m.: Go island-hopping. Take the ten-minute ferry from Liberty to Ellis Island, home to an excellent museum detailing the experience of the 12 million immigrants who entered America through this port. Check the passenger manifests or outdoor Wall of Honor for any family names, before taking the 12:20 boat back to Manhattan.

12:30 p.m.: Pay your respects at a living memorial. Walk up Trinity Place to the former World Trade Center site. Peer through the chain-link fence at ground zero, a gaping, seven-story hole in the earth now in the process of becoming the Freedom Tower, then cross the street to St. Paul’s Chapel. An informal 9/11 memorial has sprung up on the altar at the tiny, eighteenth-century church, which fed and sheltered rescue workers in the days following the terrorist attacks.

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 twenties fireboat house, where the dark-chocolate hot fudge is crafted by Ellen Sternau, 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, enjoy 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 cobblestone 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—a.k.a. “Frauda”—handbags).

8 p.m.: Gobble, then ogle at a local landmark. Dine downtown at Gotham Bar and Grill or a newer star, like Slow Food haven Blue Hill, which uses ingredients bought that morning at the Union Square Greenmarket. After dinner, stroll three-quarters of a mile 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 Cabana.