Destinations New York City: 3 Ways in 3 Days

Day 1: New York classics

For all that changes in a New York minute, plenty of places have stood the test of time. Get your bearings by walking through Midtown Manhattan, stopping to check out some of the most iconic sights.

Explore the Beaux-Arts beauty of the New York Public Library, the art deco style of the Empire State Building and the landmark Grand Central Terminal. Not just for commuters, it’s a place where you can fuel up with trendy eats (tacos, donuts, lobster rolls) in the Dining Concourse or just-shucked oysters and chowder at the century-old Grand Central Oyster Bar.

Trade skyscrapers for towering trees with a walk or a bike ride through Central Park, approximately 840 acres of green stretching from 59th Street to 110th Street — with plenty of photo ops that include a castle, a zoo and a canoe-dotted pond alongside a boathouse. You can also sign up for one of the Central Park Conservancy’s tours covering Strawberry Fields or kid-friendly nature hikes.

Cap a classic New York day with a Broadway musical. You can scout discount tickets at todaytix.com or browse last-minute options via the TKTS app, website or flagship booth in Times Square. After the show, wander over to The Rum House, an intimate cabaret-style piano bar, for one of its creative house cocktails.

Insider scoop: For one of the city’s best views, purchase timed tickets to visit the Top of the Rock Observation Deck without having to wait on line.

Day 2: History on the Hudson River

New York’s mark on the American story is indelible, and you can get a close look at that history with a boat cruise to Ellis Island and the Statue of Liberty. (Allow about three hours for Ellis Island and five hours to visit both.) Buy tickets in advance from Statue City Cruises, authorized by the National Park Service, which offers service to both islands departing from The Battery.

Don’t miss the free, park ranger-led 45-minute tour at the Immigration Museum at Ellis Island, on the site where more than 12 million people entered the United States during the late 1800s and early 1900s.

Post-tour, go for a drink and oysters at the red brick Fraunces Tavern, where then-General George Washington bid farewell to his officers at the end of the Revolution.

Heading north along the Hudson River, a visit to the glassy Whitney Museum of American Art, located in the Meatpacking District, offers more contemporary perspectives on the country and its culture. Tip: Save on admission with pay-what-you-wish tickets on Fridays, 7 p.m. to 10 p.m.

Insider scoop: After browsing the area’s art galleries and boutiques, relax with a drink at the enchanting Gallow Green at the McKittrick Hotel, a tucked-away rooftop bar and restaurant.

Day 3: Slices of Brooklyn

It’s remarkable to think that just a decade ago it could be tough to convince some taxi drivers to venture from Manhattan to Brooklyn. Today, the city’s most populous borough is practically its own global brand. A fitting introduction is to walk across the 1-mile-long Brooklyn Bridge, built in 1883 and considered one of the top engineering feats of the 19th century. Snapping photos on the bridge is a tourist experience even the locals can’t resist. 

With an appetite worked up, fall in line with the inevitable crowd outside of the original Grimaldi’s Pizzeria, famous for coal-fired, brick oven pies. For something more upscale, have a farm-to-table lunch at The Osprey at the sleek 1 Hotel Brooklyn Bridge.

After, go on a hunt for oddball souvenirs — Brooklyn-theme tea towels, vintage kimonos, locally made pottery — at the Brooklyn Flea, a cluster of vendors and food trucks that convene under the archway of the Manhattan Bridge on Sundays (running April to October). You’ll also want to pop into the many design stores, clothing boutiques, art galleries and independent bookstores nestled in the storefronts and converted warehouse buildings lining the neighborhood’s cobblestone streets.

Have your cameras ready for the Lower Manhattan views you’ll spy as you amble along the East River through Brooklyn Bridge Park. This 85-acre, waterfront green space with six piers is a favorite of locals who wander the landscaped pathways, use the sports courts and playgrounds, and meet up for picnics at the grilling areas. To end the day on a sweet note, order a homemade scoop (or two) from the Brooklyn Ice Cream Factory.

Insider scoop: For only $2, you can ride Jane’s Carousel, a restored 1922 carousel. It’s open Thursday to Sunday in winter and every day except Tuesday in summer.

— With additional reporting from Life and Money by Citi editors.