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New York City arguably packs in more culture than any place in the world—an accomplishment that can be overwhelming for both visitors and residents alike. One tour company Context Travel, which is accustomed to working in other cultural behemoths like Rome, Paris, Florence and Venice, helps organize the chaos by offering highly focused, scholar (or “docent”)-led walks. Each one is meant to be, in the words of Paul Bennett, who founded Context with his wife Lani Bevacqua, “like going back to college for three hours.” Some of the walks are more in line with upper-level seminars—Dutch and Flemish Painting at the Met for instance—while others revolve around a larger area or subject. Examples of the latter include a Chelsea gallery tour with art world insiders, and a more off-the-beaten-path walk through Jackson Heights, Queens, which explores the area’s architecture and cultural history. Indagare recently chatted with Context Travel’s Paul Bennett to learn more about the company’s New York City itineraries.

In a city like New York, you could conceivably offer hundreds of tours just inside the Met. How did you come up with these specific trips? PhDs are the bread and butter of Context Travel. A while ago, it happened that several of our scholars, or docents, from Europe were all heading to New York to either finish their graduate work or take on new positions. We decided then to move with them. Our walking itineraries came about organically and were proposed by our docents, based upon their current projects and jobs. Many, for instance, are curators at the various museums we visit.

What’s your most popular trip? Believe it or not, in terms of numbers, our trip to the Cloisters, which houses the Met’s collection of medieval art and architecture from Western Europe, is currently the most popular. This is a really fascinating collection, arranged in a very particular way, but many people—particularly those from New York or those who visit often—find it too complex to visit on their own. Thus, the appeal of going with a scholar.

Your trips focus on a specific theme or aspect of New York City—Italian Painting at the Met, for instance, or chocolate shops in SoHo. What tour is best for those who want a more general introduction to the city? At the moment, we don’t offer any really broad orientation tours for NYC. On our Architecture of NYC walk, though, architecture—particularly the various buildings on 42nd Street—is really a lens for viewing the dynamic aspect of New York City.

Do you need to have a background in art or art history to really appreciate your trips to the Met? Like a college student, you need not be an expert but you have to be primed for intellectual adventure and interested in learning about the subject at hand.

What trips, if any, are best for families? The teenagers on our trips tend to be very well-educated and interested in the walk’s subject. The tours then usually come out just like the adult ones (and the teenagers often ask better questions!). For kids under twelve, we find it’s best to tailor the walks to the child’s particular interest. Many young boys are interested in gladiators so the Greek and Roman collection is particularly popular. We’ll also bring along sketch pads and create special activities like treasure hunts. Symbols of Rome—like the eagle, which can be found on both coins and gladiator outfits—was the theme of one such hunt. This June, though, we will put together a more official family program for New York City, with tours designed just for young children (and their parents).

What’s your favorite trip? I go through phases. At the moment, it’s our Archeology of NYC tour, which stops at various digs and sites throughout lower Manhattan. We recruited an archeologist, who has access to the city’s Unearthed Archeology Center at the South Street Seaport Museum’s—a center normally closed off to the public—to help put together this walk.

Do you have a lot of solo travelers on your tours? We tend to get more couples than single travelers. Meeting new people though, is part of the charm of the group experience. Our tours are three hours long and many couples become friends afterward, arranging times to meet up for drinks, etc. before heading home.

What city is next? Istanbul. We’ve recruited several scholars and the program should launch this fall.

Walks start at $55/person. Custom tours also available.