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.

Jonathan Jacobs
Jonathan Jacobs

Name: Jonathan Jacobs

Occupation: Partner, Digital Natives Group. We’re a digital marketing agency specializing in publishing marketing (non-fiction), and travel/lifestyle. Started the agency out of school five years ago, and hard to believe we’re still going!

Hometown: Smithtown, NY

Residence: Long Island City, NY

College: Georgetown University

College major: Marketing, and Operations Management

Website: twoifbyair.com

Twitter: @TwoIfByAir

Instagram: jonathanjacobs89

Short bio: Jonathan Jacobs is a partner at Digital Natives Group, a digital marketing agency in Long Island City, NY. On the side, he’s launching Two If By Air, a travel blog, with a friend from junior high. He travels the country for work, and the world for adventure!

How often do you fly? Usually at least once or twice a month, if not more. This year I’ve had a really heavy load!

How many countries have you been to? 30!

How many continents have you been to?: 4

Favorite American city: That’s tough, but of the places I’ve been: Washington, DC, Nashville, TN and San Diego, CA.

Favorite international city: Tie—Florence, Italy and Chiang Mai, Thailand.

I have no desire to go to: Cancun.

Friendliest people in the world: Everywhere!

Country with the meanest immigration officers: I’ve never had a bad experience with immigration! (knocks wood three times…).

Favorite World Heritage Site: The Medina in Fez, Morocco.

Favorite airline: Hm. My loyalty is to Delta, but my favorite product in the skies is Emirates. Hard to beat.

Favorite aircraft type: Nothing beats a 747.

Aisle or window: Aisle! I go to the bathroom too much…

Favorite airport lounge: I love the SkyClubs at Narita.

Favorite U.S. airport: They might be troubled, but I couldn’t get anywhere without my hometown airports of JFK and LGA.

Favorite international airport: HKG!

Favorite travel credit card: I never leave home without my Citi Prestige.

Favorite island: Singapore.

Favorite beach: The Moroccan shores of the Mediterranean, specifically in Tetouan. Once spent a day on a private beach there, and I’ll never forget that experience.

Favorite fancy restaurant: I always try to have one “fancy meal” on every trip.

Favorite hole-in-the-wall: Jack’s Bar on the Chao Phraya in Bangkok. While traveling to Thailand in 2013, Mike (my blog partner) and I were desperate to find a bar-restaurant to have a small bite at, a few beers, and enjoy the warm weather (it was November back in the US). We spotted Jack a few times while riding on the water, and knew it was going to become our place. Sandwiched in-between the Shangri-La and the Mandarin, Jack’s is everything you’ll never find at either establishment. Cheap beer, greasy (read: delicious) food and a run-down restaurant on a dock with few other patrons whenever you come by. We’d cap every night, or start it, at Jack’s, with a tall Chang beer, and an order of spring rolls (though we were told, several times, to order the green curry). Our favorite thing about Jack’s? Every night we went in (five in total) he had the same concert DVD from Andrea Bocelli playing: “Andrea Bocelli: Love in Portofino.”

Favorite food: Sushi.

Least favorite food: Beets, and anything with star anise.

Drink of choice (in the air and on the ground): Bourbon on the rocks. In the air, it’s always Woodford Reserve (and American just upped its bourbon game to match Delta!).

Favorite travel movie(s): Can I say Up in The Air? I know most people saw that as a cautionary tale, but I saw that movie and thought it was an aspirational tale for travelers.

Right now I am reading: I’ve always got one fiction and one non-fiction book going, so right now it’s “Team of Teams” by Gen. Stanley McChrystal, and “The Unbearable Lightness of Being” by Milan Kundera.

Favorite travel website(s)—besides JohnnyJet.com, of course!: I’d be lost without Rene’s Points, The Flight Deal, Laptop Travel, and I’ve become a huge fan of Milenomics.

5 things you bring on a plane: A book to read (or two), headphones, an eye mask (I can’t sleep otherwise), a pack of gum, and a desire to explore!

What do you always seem to forget? I rarely outright forget something, but the closest I come is forgetting to grab the credit card I booked an international ticket on before traveling abroad! The one time I did outright forget, it meant I had to book another ticket from TPE-SIN on EVA!

What do you like least about travel? Other travelers, but mostly at airport security. Collectively, they act like they never know security is coming, and that’s what makes it such a difficult experience. ”Oh, you mean I should take my daughter out of the stroller? That’s how this works?” “Wait, the change comes OUT of my pocket? I thought I leave a trail as I walk through the metal detector, so I can find my way back!”

What do you want your loved one to buy you from an airport Duty Free store? The only souvenir I need is a snow globe. I collect them from all over the world. I have 150+ now!

Most embarrassing travel moment: (tie – two things in the same day!) While visiting the Hassan II Mosque in Casablanca, I tried to take a shortcut during our tour, and in the process I knocked over a rope and pair of crowd control posts. It was loud, and a few dozen people noticed. However, I topped myself that night, when we went out to dinner at a quasi-jazz club for a friend’s birthday. After a short search for the restroom after a few glasses of wine, I managed to stumble upon it and found a stall. When I exited and began washing my hands, I was yanked out by two employees. Inadvertently, I had used the women’s room. Yea, that was bad.

I’m embarrassed I haven’t been to: Portland, OR (to visit my sister, who has been there for 15 years), and Greece and Turkey. If I had a dollar for every time I’ve been told I’d love Greece and/or Turkey, I could buy enough RT tickets to visit there once a month.

Worst travel moment: In Rabat, friends and I thought we were asking a truck driver for a lift. Turns out the driver was a cop, and he wanted to arrest us because he thought it was our abandoned truck!

What’s your dream destination?: Right now, it’s Giraffe Manor in Kenya.

Best travel tip: On planning: do what makes you happy. Blogs about points, airfare deals, and all the rest, are great, but a great fare to Lisbon means nothing if it’s not on your bucket list. Don’t feel bad because you redeemed points for a worse cent value than somebody suggests on their blog, only worry about going on a trip that means something to you. For instance, I’m using Delta SkyMiles to fly to the DR this summer in First. I know it’s not a great value, but I’m using it to spend a week with friends on the beach. Can’t put a price on what that means to me. On exploring: I have one simple rule for safety: if I wouldn’t go down this street in New York City, I won’t go down it here.

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