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Washington, D.C.: Insider’s Guide

by Paul Bennett | December 11, 2014

The insider advice on this page is from one of Wendy’s Trusted Travel Experts for cultural city tours: Paul Bennett of Context Travel.

Trusted Travel Expert
Paul Bennett

Seeking a private guide or a very-small-group tour for an insider’s experience of a city? Paul Bennett, an award-winning writer for National Geographic and author of several books about architecture and landscape, founded Context Travel in 2003, and today his company offers cultural walks in dozens of cities worldwide. Each tour is designed and led by a scholar or expert—in disciplines including archaeology, art history, cuisine, urban planning, history, environmental science, and classics. These professors, chefs, and other noteworthy locals provide exceptional insight and open doors that would otherwise be closed to most travelers. They offer family-friendly walks too, some of which involve treasure hunts. NOTE: Unlike others on The WOW List, Paul and his team do not arrange full-service multi-day trips; they book half-day and day tours only (no accommodations or transportation). When you submit your trip request via, Paul’s team will connect you with the right Context regional expert for your trip, so you can get personalized answers and custom tour recommendations.

Two-hour tours start at $85 per person; the company does not book accommodations or make other travel arrangements.

Where to Eat

Restaurant the locals love
The Passenger at 1021 Seventh Street, NW, is part of DC’s current culinary renaissance. It opened in 2009, and is located just outside the Mt. Vernon Square/Convention Center Metro stop. Owner Derek Brown is one of the most respected mixologists in the world, and he and his bar staff will whip up a cocktail based on whatever ingredients you want. The Passenger doesn’t have a set menu, but you can’t go wrong. If given the opportunity, go for the Kimchi Dog (hot dog with kimchi, cream cheese, and sriracha) or the Chilaquilas (a fried tortilla with mole sauce, topped with an egg and avocado).

Kogod Courtyard Washington, D.C.

Kogod Courtyard, Washington, D.C. Photo: Zack Frank, Smithsonian American Art Museum (Smithsonian American Art Museum)/Wikimedia Commons

Prime picnic spot
Light-filled, glass-canopied Kogod Courtyard is tucked away from the hustle and bustle inside the Greek Revival building that houses the National Portrait Gallery. It’s quiet (unless there’s a free concert going on) and elegant, landscaped with trees, plantings, and water scrims on the floor. For an outdoor green space, go to Meridian Hill Park, a nineteenth-century Italianate estate containing one of the largest cascade fountains in North America.

What to See and Do

Oak Hill Cemetery, Washington, D.C.

Oak Hill Cemetery, Washington, D.C. Photo: AgnosticPreachersKid/Wikimedia Commons

Don’t miss
Oak Hill Cemetery is a peaceful 22-acre enclave of terraced gardens and winding paths on Rock Creek in Georgetown. Established by native son William Wilson Corcoran (of the Corcoran Gallery) on land he purchased in 1848, Oak Hill is peppered with the graves of nineteenth-century philanthropists, politicians, and other public figures. Two of its structures are on the National Register: a Gothic Revival chapel designed by James Renwick (architect of Smithsonian Castle on the Washington Mall and St. Patrick’s Cathedral in New York), and the Van Ness Mausoleum, a replica of the Temple of Vesta in Rome.

Dumbarton Oaks is an eclectic museum and gardens tucked away in a residential neighborhood, a mile and a half from the closest Metro stop. Owned by Harvard, the former mansion features world-class pre-Columbian and Byzantine art and artifacts, impressive architecture designed by Philip Johnson, and a beautiful 27-acre garden and park. It’s never crowded, and as a bonus, it’s a short stroll away from an outstanding small museum, Tudor Place, as well as the Georgetown commercial district.

Don’t bother
This may not be a popular opinion, but we’ll say it anyway: Ben’s Chili Bowl. The place has an unbeatable story that goes back to the neighborhood’s heyday, when U Street was known as “Black Broadway” and jazz legends supped here. Today the Chili Bowl stands as a symbol of black culture, social activism, and sheer tenacity. Mayor Adrian Fenty has called it “the soul of a neighborhood” and took President-elect Barack Obama here as a welcome-to-Washington gesture. But let’s face it: The food is unimpressive. Even the chili half-smoke is meh, indistinguishable from any other hot dog topped with chili.

Cheap thrill
The Smithsonian’s National Zoo. It’s a free world-class institution, easily accessible from two Metro stops and with plenty of great food and quirky shopping nearby, and big enough to occupy hours of your time. Just bring walking shoes and water, because it’s located on the side of a hill and there’s no tram or skywalk to give you a boost.

The space shuttle Discovery is on display at the National Air and Space Museum in Washington, D.C.

The space shuttle Discovery is on display at the National Air and Space Museum in Washington, D.C. Photo: Smithsonian National Air and Space Museum

Bragging rights
Get an in-depth private tour of the National Air and Space Museum from a space-policy expert. The museum has a fascinating collection, but it’s hard to get a sense of its importance without a specialist’s understanding of the Cold War-era drama of the Space Race.

Instagram moment
One of the best views of the capital is from the Curtis-Lee Mansion on top of the hill in Arlington National Cemetery.

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Best Times to Go

After Labor Day in the fall, or before Memorial Day in the spring, thus avoiding the high season while taking advantage of the balmy weather. Visiting midweek will ensure the museums and historic sites are quieter, but taking a weekend trip will get you cheaper hotel rates since most spring and fall visitors are in town for business, not pleasure.

Worst Times to Go

From the beginning of June to the end of August, the city is unbearably hot and humid, and museums and other attractions are packed to the gills.

Biggest Rookie Mistake

Getting your compass points mixed up. DC roads are based on a quadrant system, so if you’re trying to go to Ford’s Theatre, for instance, make sure you set your GPS for 511 Tenth Street, Northwest. That same address in the northeast or southeast quadrant puts you in a residential neighborhood, and in the southwest it’s a tunnel going underneath an office complex. Other common blunders: using paper tickets for the Metro (get a SmarTrip card and save $1 every time you swipe it) and showing up unexpectedly at the White House. Tours of the Executive Mansion must be arranged through your member of Congress. Book early! Reservations are accepted up to six months (but not less than three weeks) in advance.

Must-Have Apps

The National Park Service National Mall mobile app, which provides an overview of the city center and detailed information on every memorial and historic spot.

Airport Intel

If you’re visiting DC primarily to spend time in the city, then flying in and out of Reagan National (DCA) is infinitely easier than Dulles (IAD) or BWI. Tickets are generally a bit more expensive, but the proximity to DC and accessibility of the Metro at DCA more than make up for it. All three airports are busy, but DCA has the shortest screening lines even during peak hours, and distances are relatively short between arrival gate and baggage claim and curbside. Pro tip: If you take the Metro to DCA for your outbound flight and it leaves from Terminal C, ride in one of the last cars—you will exit the train right near the escalators that take you to the moving walkway into the terminal. If you’re flying out of Terminal A, ride in one of the first cars.


Her infectious enthusiasm was…

Mary Lou Desmond | April 15, 2019

The guide was savvy and friendly

Dana Perry | January 14, 2019

Hands down a highlight of my trip

Kristie Jochmann | December 4, 2018
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