The insider advice on this page is from one of Wendy’s Trusted Travel Experts for cultural city tours: Paul Bennett of Context Travel.
An award-winning writer for National Geographic and National Geographic Adventure and author of several books about architecture and landscape, Paul Bennett launched Context Travel in 2003. Context Travel runs in-depth cultural walking tours in cities throughout the United States, Europe, and Asia for groups of up to six travelers. Each tour is designed and led by a scholar or specialist—in disciplines including archaeology, art history, cuisine, urban planning, history, environmental science, and classics. These professors, researchers, and experts in their field provide exceptional insight and open doors that would otherwise be closed to most travelers. Paul and his team, who prefer to call Context Travel an “untour company,” recently introduced a series of family walks, some of which involve treasure hunts. Paul was also included in Perrin’s People, Wendy’s award-winning list of top travel specialists, which was published annually in Condé Nast Traveler magazine from 2000 to 2013. Context Travel’s U.S. programs—which include walks in New York; Washington, D.C.; Boston; and Philadelphia—are run by Carolyn Macuga, an art historian.
Where to Eat and Drink
Restaurant the locals love
Jimmy’s 43, at 43 East Seventh Street in Manhattan, is a locavore gastropub nestled underground in the eclectic St. Mark’s Church-on-the-Bowery area of the East Village. Frequented by longtime residents and students alike, it has an ever-changing seasonal menu and a superb selection of beers, both local brews and imports. Recommended: the deep, flavorful smoked sausage and the ultrarich duck cassoulet, accompanied by a pint of craft beer.
Best spot for a drink
Stop for a glass of wine or a cocktail at the iconic Four Seasons Restaurant. Designed by Philip Johnson and Mies van der Rohe in 1959, this landmarked space is an authentic portal to the glamour of Mad Men–era Manhattan.
Prime picnic spot
Head north to Fort Washington Park, at the far end of the 11-mile Hudson River Greenway, and spread your picnic in a grassy meadow near Jeffrey’s Hook Light House at the foot of the towering George Washington Bridge. Fondly known as the Little Red Light House, Manhattan’s only remaining beacon once guided ships through the narrow river passage. Alternatively, climb Lookout Hill in Prospect Park, the highest point in Brooklyn—a magical spot with views of the 585-acre Olmsted/Vaux–designed park, the low-lying roofscape of brownstone Brooklyn, and, on clear winter days, the Coney Island Ferris wheel and the bay beyond.
What to See and Do
The Morgan Library, originally the private collection of Gilded Age financier Pierpont Morgan, houses such prizes as three Gutenberg Bibles, autograph music manuscripts by Wolfgang Amadeus Mozart, the only surviving manuscript of John Milton’s Paradise Lost, and the largest collection of Rembrandt prints in this country.
The map room at the New York Public Library‘s main branch at Bryant Park is a delight for anyone who loves geography and travel. Holding close to half a million sheet maps, books, and atlases going back to the fifteenth century, it can transport a visitor to any place and time. Just down the street from the NYPL, the interior of the Old Bowery Savings Bank at 110 East 42 Street, not far from Grand Central Terminal, is a cavernous Italian Romanesque Rival masterpiece, complete with intact bankers’ windows—a glimpse of financial Manhattan from the era of Prohibition and the Great Depression. Although the Cipriani-owned space is not typically open to the public, the doorman will often allow passersby to sneak a peek when it is not being used for a private event.
Making the trek to Liberty Island, home to New York’s most famous statue. Lines are long, and reservations must be made months ahead if you want to visit the crown—but you can get a fabulous view of Lady Liberty and the New York Harbor from the Staten Island Ferry. As a bonus, Staten Island is well worth exploring, home to an inspiring 2,200-acre park-in-the-making (the reclaimed Freshkills landfill), New York City’s longest stretch of working waterfront (the Kill van Kull), and Snug Harbor, a landmarked collection of Greek Revival buildings that once housed elderly seamen (the grounds also include a botanical garden, a Chinese scholars garden, and performing and visual arts venues).
Wasting your time on a hop-on, hop-off bus tour from Times Square, or anywhere in the city. Many of the guides are neither licensed nor experts in the city’s history (so the content is dubious at best), and if you actually sit inside the bus you might not even see anything at all, due to the advertising plastered over the windows. Instead, book a walking tour led by a local public historian and savor the city one neighborhood at a time. You’ll learn lots more as you discover tucked-away architecture, gardens, courtyards, and art.
Join the hip young Brooklynites who turn up on Wednesdays to hear some of New York’s best folk music for free at Roots and Ruckus at the Jalopy Theater in Red Hook. The venue itself is worth the trip: It is decked out to look like a workingman’s chapel from the 1890s, perfectly fitting the soulful and earthy music.
Rendezvous with a Met art historian and prowl the museum in privacy—after the crowds leave and before the lights go out for the night. The Metropolitan Museum of Art is one of the most comprehensive and busiest museums in the world and not to be missed, whether it is your first or tenth visit, and there is nothing quite like having the galleries to yourself. But don’t go hog-wild just because you can. Take your time and immerse yourself in one collection. The choices are luscious and overwhelming, so if you’re stumped, flip a coin; rushing from ancient Egypt to sixth-century China to the Italian renaissance will only make you crazy.
Right after Columbus Day weekend is prime time in New York City. The locals are back from their summer vacations and the city is buzzing along, business as usual. In October, park woodlands and tree-lined promenades are dressed in warm, rich colors, and the fall exhibitions have been open for a few weeks, so lines have shortened.
Skip Manhattan between Thanksgiving and New Year’s Day, when it is swarming with holiday shoppers. Steer clear, too, on St. Patrick’s Day, when streets are packed with revelers and navigation is a nightmare.
Spending way too much time in taxis. The best way to see New York is by foot, and finding your way around is easy because of the grid layout (avenues run north–south, streets east–west). For longer distances, take the subway or a bus. You’ll get there faster than you would in a cab, and you’ll save a small fortune.
The corner of Broadway and Broome in SoHo. From here you can see the tallest structures in the city: the Freedom Tower, Trinity Church, the Woolworth Building, and the Empire State Building. It’s also the corner of the EV Haughwout building, the largest and most marvelous cast-iron masterpiece in the city and one of our favorite buildings for its stately timelessness. For a sunset shot of the harbor and the Statue of Liberty, head to the Valentino Pier in Red Hook, Brooklyn.
Any piece that catches your eye from a street-art vendor on Prince Street in SoHo. Not only will you have a one-of-a-kind visual reminder of your experience but you will also support a local artist. You might even get lucky and acquire something quite valuable at a bargain price. It’s been known to happen: During a recent visit to New York, Banksy sold prints of his work for $60 on the streets near Central Park.
Compact binoculars—especially good for zooming in on architectural details that you would otherwise miss.