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Gregory Diehl
Gregory Diehl

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.

Name: Gregory Diehl

Occupation: Author, Consultant and Coach

Hometown: Encinitas, California, USA

Residence: All over the world, but I have home bases in Vilcabamba, Ecuador and Tbilisi, Georgia

College: None

College major: None


Twitter: @gregoryvdiehl 

Facebook: Gregory V. Diehl

Instagram: gregorydiehl

YouTube: Gregory V. Diehl

Short bio: I left California at 18 to explore our world and learn about myself. Now I write books and help people figure out their identities in business and life. My first book, Brand Identity Breakthrough, is an Amazon business bestseller. My new book, “Travel As Transformation,” chronicles the personal evolution worldwide exploration has brought to me and others.

How often do you fly? Recently, just about every month or two. But it changes frequently. I like to stay a while in one place to really get to experience life there.

How many countries have you been to? 45, if you count territories and overseas territories.

How many continents have you been to? Five: North America, South America, Europe, Africa, and Asia.

Earliest travel memory: My first trip abroad was at 18. I spent nine months visiting a friend in Costa Rica. That was where I realized the life-changing potential of travel and I became obsessed with seeing more of the world.

Least favorite country: China, for a lot of reasons I don’t have the space or emotional capacity to go into here. There’s a whole chapter about it in my book.

I have no desire to go to: Most of the big cities everyone raves about.

Friendliest people in the world: Filipinos.

Country with the meanest immigration officers: The UK border guards interrogated me for two hours because I told them I was going to be housesitting for a friend. They thought it meant I was coming there to work illegally. It doesn’t exactly make me want to go back.

Aisle or window: Aisle. I have the world’s smallest bladder.

Favorite island: Mindanao, Philippines.

Favorite fruit: I’m hurryin’ for durian.

Favorite travel movie(s): Cast Away.

Favorite travel book(s): “Walden.”

Right now I am reading: “Travel As Transformation.”

5 things you bring on a plane:

  1. Laptop so I can work
  2. Noise-canceling headphones so I can escape other people
  3. Dark chocolate to ease the stress of flying
  4. Music to dull the madness
  5. About a million movies

What do you always seem to forget? Checking in to my flight online.

What do you like least about travel? Being crammed into small spaces and crowded with other travelers.

I’m embarrassed I haven’t been to: Oceania.

Worst travel moment: Getting sick for days from Indian street food in Delhi.

What’s your dream destination? Ecuador—or anywhere with a lot of wildlife.

Best travel tip: Travel to places that challenge you. Don’t just go where it is easy. Stretch the limits of your awareness. 

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