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Want to know how to travel in style, just like the pros? We check in with frequent fliers to find out how often they fly, their favorite destinations and what they never leave home without.

Stephen Oddo
Stephen Oddo

Name: Stephen Oddo

Occupation: Co-Founder, Walks of Italy & Walks of New York

Hometown: San Diego, CA

Residence: New York, NY

College: UC Santa Barbara

College major: Psychology, Physical Anthropology (& Archaeology), Philosophy Minor—Phi Beta Kappa

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Short bio: Stephen was raised in a tourism industry family that instilled the value of world travel. He moved to Rome, Italy in 2005 tracing his Italian heritage and becoming actively involved in tourism. In 2009, he co-founded a travel agency selling tickets and tours adjacent Vatican City. Shortly thereafter he partnered with travel expert Jason Spiehler to found WalksofItaly.com, a travel company for Italy visitors offering unique sightseeing tours & activities. Since then, Walks of Italy has become one of the largest operators of online à la carte travel services in Italy, a success he attributes largely to social media and content marketing strategies. Stephen then launched Walks of New York in 2014 to great success, including coverage in The New York Times and a partnership with chef Mario Batali. He oversees offices in Rome and Austin, TX. Stephen was featured as a key character in a NatGeo documentary about traveling smart in Rome, and has traveled the globe extensively to over 50 countries.

How often do you fly? At least once a month, average 100K miles per year.

How many countries have you been to? 54

How many continents have you been to? 5

Earliest travel memory: A few visits to Cabo San Lucas when my father was GM at the Hotel Palmilla, chatting with a macaw (bird, like a parrot) named Paco.

Favorite American city: New York or New Orleans.

Favorite international city: Rome or Naples.

Least favorite country: Cuba—but that’s another story, and I’ve yet to visit Havana.

Country with the meanest immigration officers: England, Finland.

Favorite World Heritage Site: Amphitheatre of El Jem, Tunisia.

Favorite airline(s): Love to fly Virgin or most Middle Eastern airlines…but most frequently am found on Delta.

Favorite aircraft type: Boeing 747 or Airbus A380.

Aisle or window: Depends on distance and if I need to sleep, but generally aisle—I like to #takewalks :)

Best flight attendant you’ve ever had: On an American Airlines flight from Miami to NYC. She was wonderful!

Favorite airport lounge: London—Virgin, there is nothing like this I’ve seen elsewhere!

Favorite U.S. airport: Austin, TX.

Favorite international airport: Schiphol, Amsterdam.

Favorite ho Mandarin Oriental Hong Kong.

Favorite cruise line: None.

Favorite travel credit card: Chase Sapphire.

Favorite island: Sicily.

Favorite beach: Praia Mole, Florianopolis, Brazil.

Favorite fancy restaurant: Del Posto, NYC.

Favorite hole-in-the-wall: Roberto’s Taco Shop in Del Mar, CA.

Favorite bar: Botticella, Rome, Italy.

Favorite fruit: Passion fruit.

Favorite food: Bucatini all’amatriciana.

Least favorite food: N/a.

Drink of choice (in the air and on the ground): White wine.

Favorite travel movie(s): L’auberge Espagnole.

Favorite travel show(s): No Reservations.

Favorite travel book(s): Anything Bill Bryson.

Right now I am reading: “The Once and Future King.”

Top 3 favorite travel newsletters/magazines/blogs: TravelBareFeet.com.

Favorite travel website(s)—besides Hundredbacklinks.com, of course! Anything “Walks of”! :)

5 things you bring on a plane: MacBook Air, chargers, drink vouchers, GoGo in-flight subscription, jacket!

What do you always seem to forget? Toothbrush!!!

What do you like least about travel? Sitting on the tarmac without reason.

What do you want your loved one to buy you from an airport Duty Free store? Soda water making machine.

Favorite travel app(s): Kayak, Google Maps, HotelTonight.

Most embarrassing travel moment: Missing two flights in a row, two days in a row, from Cologne to Moscow.

Worst travel moment: Trying to catch a connecting flight from San Salvador, El Salvador when I meant to fly to El Salvador, Chile! Old days of travel search were not always clear in this regard.

What’s your dream destination? Egypt. 

Favorite travel charity: Venice in Peril.

Best travel tip: Get outside your comfort zone, eat what the locals are eating, book high-rated sightseeing tours, go off the beaten path, and #takewalks!

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