Matthew Bailey
Matthew Bailey

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: Matthew Bailey 

Occupation: Writer, Photographer, Travel Host, Entrepreneur

Hometown: Originally from Fort McMurray, Alberta, Canada

Residence: Now living in Calgary, Alberta, Canada

College: S.A.I.T and the University of Lethbridge

College major: Business Admin/Marketing and Bachelor of Management

Website:,, and

Twitter: @matthewgbailey

Facebook: Live Limitless and Must Do Canada

Instagram: matthewgbailey

YouTube: Must Do Canada

Short bio: Grew up in a small Northern Canadian mining town. Decided that I wanted to see the world and become a “new” person. Moved to a new city and eventually left to Australia, New Zealand and Indonesia for five months. Found my adventurous side, gained a lot of confidence, got married, started writing, and traveled with my wife to six continents and 35 countries over the span of about five years. Also developed a 100-item list of goals I wanted to accomplish and crossed them all off by the age of 31. Things like acting in a movie, being interviewed on TV, and speaking in front of a large audience. Started developing my entrepreneurial side and developed a couple of websites and blogs as well as creating a massive 150-day multimedia road trip across Canada. My love for travel also turned me into a travel hacker, racking up more than 2,000,000 points and experiencing things I never would have experienced otherwise such as first class flights on Emirates and business class trips around the world. It also lead to my first online business, a travel hacking site for Canadians.

How often do you fly? For me it varies quite a bit. Some years, I fly 20+ times and other years just 2-3 times.

How many countries have you been to? 35

How many continents have you been to? 6

Earliest travel memory: Visiting family in Newfoundland, Canada and my first international trip to Denmark.

Favorite American city: So tough as I haven’t been to all of them but I do like Seattle, Portland, and Los Angeles.

Favorite international city: This is a tougher question as I love so many. Some that come to mind are Vancouver, Amsterdam, Mexico City, Bangkok, Singapore, Tokyo, and Shanghai. Haha, I could keep going.

Least favorite country: None. I’ve liked them all in different ways. There are definitely some areas or cities I’ve liked less than others but countries as a whole, I don’t think so.

I have no desire to go to: Major tourist attractions.

Friendliest people in the world: Myanmar stands out the most but also Canada.

Country with the meanest immigration officers: I’m not sure about an entire country but I definitely hate transiting through Houston’s airport.

Favorite World Heritage Site: Angkor Wat stands out as pretty incredible and unique. I also love Banff National Park and Nahanni National Park.

Favorite airline: Emirates but mainly because of the first class experience I had. Literally.

Favorite aircraft type: Nothing specific but I love the big jets used for international travel.

Aisle or window: Window, always.

Favorite airport lounge: Dubai’s.

Favorite U.S. airport: I don’t have a favorite.

Favorite international airport: I don’t really have one but it’s always nice to see a Canadian airport as it means I’m coming home after a long trip.

Favorite hotel: Tough call. I don’t really have a favorite hotel but I loved Las Brisas in Ixtapa, the St.Regis in Singapore, and any hotel with an incredible view.

Favorite cruise line: Haven’t been!

Favorite travel credit card: American Express.

Favorite island: Hmmm. Palau and some of the islands in Indonesia (like Raja Ampat area) stand out.

Favorite beach: Almost all the beaches in western Thailand (Krabi region).

Favorite National Park: It’s tough but I’ll say Banff National Park as I’ve spent so much time there.

Favorite fancy restaurant: My favorite “restaurant” experience was at the Feast, a restaurant owned by Chef Michael Smith in Prince Edward Island, Canada.

Favorite hole-in-the-wall: Couldn’t say a specific one but many of them would be Southeast Asia and Mexico City.

Favorite bar: None in particular. Coco Bongo in Cancun comes to mind as an epic experience though.

Favorite fruit: I love so many. Blueberries, mango, strawberries, and raspberries—you name it!

Favorite food: I think as an overall food I can eat almost whenever would be pizza. But as an overall food group, I’d go with Mexican, Japanese and Thai.

Least favorite food: Dry meat or very plain food.

Drink of choice (in the air and on the ground): I drink a lot of water but also love the odd fruit juice, smoothie or soda. For alcohol, I’d say whiskey and a nice cold pint are my favorites, followed by tequila and vodka.

Favorite travel movie(s): I really liked Into The Wild but my favorite travel-related movies are somewhat documentary in nature such as Baraka and Samsara.

Favorite travel show(s): The BBC Planet Earth series.

Favorite travel book(s): “Vagabonding.”

Right now I am reading: “Homo Deus” (otherwise known as Sapiens part two) and “Bluefishing.”

Top 3 favorite travel newsletters/magazines/blogs: Once again, I don’t have favorites that come to mind. I usually search a variety of travel blogs but Nat Geo is a great magazine with incredible stories. I also like looking through a Lonely Planet book to get some ideas as to where to go, or where NOT to go.

Favorite travel website(s)—besides, of course! I use Google to research a variety of blogs but I find myself going back to Wikitravel quite often for bite-sized information on a variety of places.

5 things you bring on a plane: Earplugs, eye mask, something to read, a notepad for writing, and a camera/phone.

What do you always seem to forget? I’m actually pretty good at not forgetting anything.

What do you like least about travel? All the work involved in determining currency exchange, visas, customs, and all of that stuff. Also, with developing countries, I don’t like the hassle of dealing with all the touts and general travel scams.

What do you want your loved one to buy you from an airport Duty Free store? A bottle of alcohol. Something new that I haven’t tried before like a flavored vodka or a nice whiskey.

Favorite travel app(s): XE (currency convertor).

Most embarrassing travel moment: Having a bad case of diarrhea while going to the airport and needing to stop three times in the span of 30 minutes. Then when I made it to the flight agent after waiting in line, I couldn’t even grab my ticket as I had to run to the bathroom again.

I’m embarrassed I haven’t been to: Ireland because my grandparents are from there and I have my Irish citizenship.

Worst travel moment: We took a scenic boat trip in Guilin, China, and the boat driver decided to just leave us on the edge of the water in the middle of the forest. We had to walk back to town in the dark, not knowing where we were. Another one was a safari that we went on in Tanzania. We had been invited at a steep discount as they wanted us to be their booking agents in Canada. It’s a long story but although the experiences themselves were good (seeing the big five, etc), the overall planning and experience of the tour was a complete disaster. We lost so much time and both my wife and the woman who joined us spent many days crying and arguing with the company we were with. Maybe just read about it here.

What’s your dream destination? I don’t have anything specific in mind but overall, when I think of a dreamy destination, I think of a tropical beach with white sand, palm trees, good scuba diving, and a mellow atmosphere. I’d also like to go to Antarctica. 

Favorite travel charity: Room to Read was the first one I heard about after reading the book “Leaving Microsoft to Change the World.” However, one that stands out as well is Kiva, although I don’t think it’s considered a charity.

Best travel tip: I have two. The most important is to just go. The biggest thing holding you back is likely yourself. Travel can be cheap and it can be expensive but the worst thing to do is to keep waiting. Second is to do a little research in advance, specifically on safety. I’m not a big fan of over-researching and planning but some initial research can save you a lot of headache. For example, after researching Delhi, we knew to have our hotel SEND a taxi to the airport to pick us up. It cost a little extra but everyone we met who took a random taxi from the airport got scammed out if huge amounts of money and had their trip ruined in some way.


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