NYC Summer Weekend Itinerary

David Sokol

Summertime in New York redefines the phrase “the great outdoors,” as the City blossoms with life and culture. Cafés take to the sidewalk, neighborhood festivals sprout up across the boroughs, and public plazas and lawns play host to free concerts and movie screenings. Enclosed spaces like restaurants and museums have added appeal during summer too, because the City moves less frantically. Take advantage of the season's wealth of experiences, slower pace and perfect weather with a long weekend in NYC. To help plan your trip, we've created a three-day itinerary that takes advantage of a summer-Friday work schedule. Or consider adapting this agenda to start on a Saturday, to enjoy many hotels' lower Sunday night rates.

Central Park. Photo: Will Steacy

Day One

Spanning 843 acres, Central Park could fill three days of exploration on its own, but an early morning stroll through the southern end of the park is a wonderful way to kick off a summer weekend and get a taste of Frederick Law Olmsted and Calvert Vaux's historic vision of lush urban escape. Highlights include the Pondand Heckscher Playground, both steps from Central Park South (West 59th Street)—not to mention a parade of joggers, bikers and horse-drawn carriages working the lower loop. Sate your appetite back at Sarabeth's Central Park South, dining under the charming ceiling murals. This NYC institution, with its baked goods, jams and extensive list of egg dishes, is particularly suited for breakfast or brunch.

It's a short walk from Sarabeth's to any number of subways, which can whisk you to Lower Manhattan for the afternoon. Start this (sea) leg of the day with Statue Cruises, which ferries visitors from Battery Park to the Statue of Liberty National Monument and Ellis Island on behalf of the National Park Service. In addition to providing access to two of the most important sociocultural landmarks in the United States, the boat ride offers an unforgettable vista of downtown skyscrapers, plus unexpected sights like kayakers and cargo ships navigating New York Harbor side by side.

Go from aquatic to aerial at One World Trade Center, where you will rank among the first people to experience One World Observatory. Besides framing blimp's-eye views of greater New York City, the 1,250-foot-high space includes video and interactive technology that reveals the history of the skyline in rich detail. There are a few dining options on the middle of OWO's three levels, though consider lunching at Le District or on Stone Street as an alternative. The former is the brand-new, 25,000-square-foot French marketplace inside Brookfield Place, while the latter is reputed to be New York City's oldest paved street and holds an urban-scale buffet of restaurants and hangouts. Afterward, get ready for a night on the town with a sartorial pit stop: the Lower Manhattan flagship of the discount department store Century 21 boasts high fashion and low prices.

Courtesy, Russian Tea Room

With new outfit in tow, head back uptown to try on any number of cocktail-hour and dinner venues. The luxury-minded should consider the Grand Salon of the recently opened Baccarat Hotel & Residences, which drips with namesake crystal and feels like a piece of interior designer Gilles & Boissier's native Paris; nearby, Aldo Sohm boasts best-in-class service and an art-filled interior as well as a comparatively laid-back atmosphere. For a larger meal, the Russian Tea Room dishes up old-school glamour and modern continental cuisine, while Butter rotates seasonal ingredients across its rustic tables.

Any of these evening destinations will also put you in close range of the Theatre District, without which no New York City excursion is complete. If you didn't plan ahead of time, you can still get tickets for many shows on the day of performance either at the box office or TKTS Discount Booth. Finish the night with more entertainment at Lucille's Bar & Grill, sophisticated cocktails and conversation atop Haven Rooftop or a vigorous game of pins at Bowlmor Times Square.

Day Two

Focusing on art and culture in its many forms, the second day of this itinerary may feel worlds away from the sightseeing that inaugurated the weekend. Yet it starts just steps from where you left off, in Midtown at the Museum of Modern Art. MoMA opened in 1929 as the world's first repository devoted only to modern art, and today it counts more than 150,000 pieces in that collection, as well as attention-getting exhibitions that currently include retrospectives of Yoko Ono and Gilbert & George. The building itself (located across from the Baccarat Hotel) is a famous work of art, and over the years acclaimed architects from Edward Durell Stone and Philip Johnson to Yoshio Taniguchi have played a role in shaping it.

Bloomingdale's. Photo: Julienne Schaer

Not every architectural landmark touches terra firma, as evidenced by the Rainbow Room, whose protected art deco interior sits 65 floors above the street. The space is open to the public for regular Sunday brunch, a three-course prix fixe that comes with live jazz accompaniment to exemplify 1920s and '30s style in every respect. If all your senses haven't been tickled by the band's last notes, follow up brunch with a retail feast. Numerous upscale boutiques line Fifth Avenue and 57th Street—which also has its share of galleries, with art available for purchase—while on the edge of the Upper East Side, department stores Barneys New York and Bloomingdale's curate the world of luxury for one-stop shopping.


An emporium of a different kind awaits you further up Fifth Avenue. The Metropolitan Museum of Art consolidates the world of artistic achievement into one giant treasure chest overlooking Central Park: the City's largest museum can hold anyone's fascination, whether you're an armchair Egyptologist or envelope-pushing fashionista. And the collection is poised to expand in coming years, as architect David Chipperfield was recently selected to design a new wing for modern and contemporary art.

If you plan on following the construction project—or have any enthusiasm for design in general—supplement your Met tour with a trip to the Cooper Hewitt, Smithsonian Design Museum. The institution is the largest American museum to focus solely on the discipline. A recent renovation, overseen by a dream team of historic preservationists, digital storytellers and other talents, has added all kinds of bells, whistles and new displays to the one-time home of Andrew Carnegie.

Dutch Kills. Photo: Julienne Schaer

From Museum Mile, hop over to Lexington Avenue for a southbound subway ride and a transfer to reach one of two white-hot art destinations. Switching to a westbound L train will take you to the Meatpacking District, where the recently reopened Whitney Museum of American Art, in a new Renzo Piano–designed building, has been lauded for its visionary architecture and provocative art. Training east to Long Island City, on the other hand, reveals a whole neighborhood whose current shape is practically founded on art. Indeed, without the groundwork laid by MoMA PS1, Socrates Sculpture Park, the Noguchi Museum or Flux Factory, the East River waterfront of Queens may still be a warehouse zone (well, an area rezoning in 2001 certainly helped speed the plow). It certainly wouldn't sport the cocktail sensation Dutch Kills or foodie paradise M. Wells Dinette. Arts investments paved the way for these amenities once reserved for Manhattan. Literally so, in the case of M. Wells, which is located inside MoMA PS1.

The High Line. Photo: Tagger Yancey IV

Day Three

If you did not make it to the Whitney yesterday—or didn't get enough of it—then start this morning admiring the institution from an elevated perspective, first by pedaling a Citi Bike to Gansevoort Street. This charming patchwork of cobblestone meets both the new museum building and the foot of the celebrated High Line. The linear park grazes the Whitney, providing additional viewpoints of the architecture, and then hovers 30 feet above the streets of Manhattan all the way to Hudson Yards (please, no bikes on the elevated walkway). Consider a shorter stroll to the vicinity of Chelsea Market to sample the former factory building's culinary options.

Coney Island. Photo: Julienne Schaer

Whatever eats you choose should keep you sated while you trek over to Coney Island. For generations this corner of Brooklyn has been known worldwide as a center of amusement, and today's most entertaining gizmos still don't hold a candle to whirling on Luna Park's Cyclone roller coaster, making eye contact with an underwater denizen of the New York Aquarium or simply detouring from Coney Island's boardwalk for a refreshing dip in the Atlantic Ocean. Wrap up your celebration of all things vintage with a frank at Nathan's Famous, which is closing in on its 100th birthday, and a drink at 40-year-old Ruby's Old Tyme Bar and Grill.

Washington Square Park. Photo: Alex Lopez

Change out of your beach-going togs back at your hotel, and prepare for the home stretch of your weekend. What better way to get a memorable final impression of New York City than a leisurely tour through postcard-perfect Greenwich Village? Start in Washington Square at its most picturesque spot: the 120-year-old Washington Arch that rises triumphantly above the park.

Stay in the neighborhood for dinner at Cornelia Street Cafe and dessert at Caffe Reggio, old bohemian hangouts that continue to represent Greenwich Village's longtime support of progressive thinking. Extend your evening with a celebration of the local musical legacy at historic clubs like the Village Vanguard and Café Wha? or their 21st-century interpretation, (Le) Poisson Rouge. And if you can fit in a nightcap at Kettle of Fish, which in previous digs hosted the likes of Jack Kerouac, Edie Sedgwick and Bob Dylan, your Village circuit—and long weekend—will be complete.