In the latest Travel Tuesday Interview series, I chat with Travis Sherry, host of the #1 travel podcast on iTunes, Extra Pack of Peanuts. Travis and his wife, Heather, are the ultimate travel hacking experts. He shares his travel stories and top hacking tips in this interview.
Travel hacking expert Travis Sherry is the host of the #1 travel podcast on iTunes, Extra Pack of Peanuts. He’s been on the road almost full-time since 2010. (Photo courtesy of Travis Sherry)
Name: Travis Sherry
Age:35
Hometown: Philly
Country count: My best guess is 51.
Website: ExtraPackofPeanuts.com
1. How did you start traveling?
There are three distinct points. The first was when I was 18, I took a road trip to Florida. That was the first time I’d traveled without my family. It was me and buddy. We took a road trip from Philly to Florida to move sister into college. That was the first point where I experienced freedom. I still count it as one of the best trips I’ve had.
The second turning point was when I was 26. I traveled a bit before that. I lived for four months in Switzerland for an internship. That was the first time I lived abroad. That was a whole other experience. I was living abroad and making a life abroad. That was a distinctive moment.
The third point when I was 27. After returning home from Switzerland in 2010, Heather and I decided to move to Japan seven months later. That was the beginning of the third stage of my travel life. Travel became the main part of our life. That really opened up international travel for us a bit and this idea that this isn’t just a thing we are doing for vacation. More of our life than not is going to be spent traveling.
Travis often works from the road and makes the most of layovers by recording podcasts like in this photo from the Amsterdam airport. (Photo courtesy of Travis Sherry)
2. What does the average work day look like for you?
I’ve tried to make it more systematic and more normal. I’ll start working at 10 a.m. I might go to the gym and have an easy breakfast in the morning. The bulk of my work is done between 10 a.m. and 3 p.m. What that involves depends on the day. Some days are podcast recordings. Usually on Tuesdays we do weekly workshops. That’s my day to focus on the community we run.
Recently, it’s been a lot of big picture planning and then, organizing the team to get things done. Depending on the day, I try to do different things. Mondays are calls. Tuesdays are podcast recording. Wednesday and Thursday are more creative days—shooting videos, writing and getting into that flow. Thursday or Friday are housekeeping days like doing taxes or bookkeeping. Batch responding to emails on one day. I don’t kill the creative flow to respond to emails. I’m trying to get better at working in those zones. It’s become more systematic as it goes.
The more organized it became, the more I enjoyed it and allowed myself spontaneity. Then, the rest of the day is open after 3 p.m. Trying to batch by day has been a big thing for us. You stay in the zone.
3. Share one of your travel highlights.
My favorite trip I’ve ever taken was to the Republic of Georgia. Every time anyone would mention Georgia, they were the biggest fan of it. It had raving fans. I had very high expectations going in. Finally, Heather and I went. I was a little worried it wouldn’t live up to the lofty expectations. Fortunately, it not only lived up to it but was better than I thought. That’s the best way to describe it. Essentially, we were in Georgia and we got on this bus, and it was the wrong bus. Then, we had a feast in this women’s house and the whole town came!
It’s the only place I’ve been that’s as naturally beautiful as Switzerland. It’s more rugged and 1/10 price of Switzerland. Great food. Incredible scenery. The food was fantastic. The people were super nice. We spent 12 days there in July of 2016. It just blew me away. It was everything I wanted out of it. It’s not super touristy. Everyone was excited to have you there.
We drove the third most dangerous road in the world. We had a driver. We got to this town with a village of 50 people. It’s only open five months of year due to snowfall. You feel like you’ve gone back in time. There’s a castle up over the hill and wild horses. I asked a guy, “Whose horses are those?” He was looking at me like I was crazy. He goes, “Those are just wild horses.” I guess I never thought of that before. Out there, it’s just this awesome, neat experience that lived up to every expectation I had.
Travis’ wife, Heather, took this shot of him at Ballycarbery Castle in Ireland last year. They have been using airline miles mostly from credit cards to pay for their flights. (Photo courtesy of Travis Sherry)
4. What is the biggest myth about travel hacking?
I’ll give you two. One is the myth I believed when I started—that frequent flyer miles were only for people who traveled a lot. You don’t have to fly a lot to earn a ton of frequent flyer miles. You can do it through credit card sign ups and shopping. That’s the reason a lot of people don’t get into it. They don’t think they can earn enough to get a free flight. They think they have to be getting on planes all the time to earn the miles. You can sign up for a credit card and get a free flight to Europe with the signup bonus from the card!
The second myth is that when you earn points that it’s super hard to redeem your points. It’s hard at first but with a little bit of knowledge, you pull the veil back, and it can become something that’s easy to do.
Usually, it’s just me saying, “You aren’t looking in the right place.” It’s easier than people think if they spend time learning the right stuff.
What credit card does he recommend? Chase Sapphire Reserve for people who travel several times a year, Chase Preferred for people who travel one or two times a year.
5. Name three things you always pack for a trip.
- I always pack headphone splitters to watch a movie on the computer with Heather on flights.
- Mack’s earplugs
- Eye mask
- For guys, Bluffworks. They make men’s travel chinos, blazers and suits. All stretch and wrinkle free. I have five pairs, one in every color of the chinos. It’s the best travel clothing.
Travis works from the beach in Croatia or anywhere there is wifi! (Photo courtesy of Travis Sherry)
6. How do you balance work and travel?
Now, after of years of trying to figure it out, we try to batch work and batch travel. Instead of trying to do both at once really well. There are certain circumstances where we have to. When we are at home in Philly, that’s the time to move projects forward. That’s the time to make sure anything that needs to get done gets done. We’ve become a lot more organized that way. Then, when we are traveling, we’ve got some really big plans. We’ve got all these projects moving. We are able to tread water. It’s not that we are not working at all; we are doing things that are easier to do [and] are quick. When we are traveling, we are 80% travel and 20% work. It’s hard to build a business and travel.
We have a house in Philly. I was so opposed to moving back into a house. In August 2015, we moved back into the house. We live here when we are at home. Over the last year or two, it’s been about 50% on the road and 50% home.
7. The name of your podcast, Extra Pack of Peanuts, references your hatred of flying when you were younger. How did you overcome this fear? Any tips for others to do the same?
When I was a kid, I don’t know if was fear. I thought I would get sick, and then, I did get sick. I think some of it was naturally getting out of that [mindset]. I’m old enough to know that if you get sick on a plane, it’s not the end of the world. I think the second part was that I just ended up going on to my adult years. I just thought, “This is how I’m going to get to where I’m going to go.” Is it worth it to get sick for a day and then spend two to three weeks in Europe? The ends were worth the means.
I still don’t like flying or enjoy it. But, I also don’t mind it as much. I’m like middle ground. Maybe, I like it a little less than the average person.
Last year, Travis and Heather Sherry had their first child–Whittaker, who will turn one this year. Whittaker took his first flight when he was six months old. They are spending the holidays in their home in Philly and took Whittaker to visit a nearby pumpkin patch recently for this photo. (Photo courtesy of Travis Sherry)
8. How has having a child changed the way you travel? [His son Whittaker is turning one soon!]
It hasn’t been such a change. We still took all the trips we wanted to take. We don’t see that changing.
I guess that thing that does change is that we are going to start traveling slower, and we already have. Instead of going to four cities in 14 days, let’s do seven days in Barcelona and seven days in Budapest. I think we’ve started to slow down some and take our time.
The other big change was that we couldn’t go out at night. We were never huge partiers. We were in Budapest at 9 p.m. [and said] “I guess at some point we need to go back to get him in bed.” There needs to be a market for local babysitters so you can go out one night a week.
Since I’m getting older, there are changes I’d do anyways. We are very last minute especially me. We will book accommodation advance now and less spur of the month.
9. Share two of your favorite travel hacking tips.
The thing that has changed my life the most is just understanding how to use mile and points. Getting a good travel rewards card. Understanding how it works and how those points work. Just starting with one [card] and earning those points, then using them once [is the best way to start.]
One of the things we started doing is giving chocolates to flight attendants. I called it a trick but its’s more of a thing I just like to do. We bring chocolates for flight attendants. I make sure there’s enough for everyone on the plane. I give them to the flight attendants when I get on the plane. I say thanks for taking care of us. I appreciate it. All of it is true. That always puts a smile on their face. We’ve got upgraded to business class before because of it. They’ll come and give you free drinks. They are always super nice. It can never hurt to make the flight attendants day better.
I always pack in a carry on. We both always pack in a carry on. To me, only using a carry on eliminates a lot of stress [worrying] “Is my luggage going to get lost?” We only use carry-ons 90% of the time. Now, we might have to check a crib. We don’t have to pay baggage fees.
Travis and Heather spent a lot of time traveling around Asia when they lived in Japan and snapped this shot at Angkor Wat in Cambodia. They like to avoid spending the winter in Philly so they are heading to Mexico in January. (Photo courtesy of Travis Sherry)
10. What is your next adventure?
Our next adventure is January and February we will be spending in Mexico. We will be spending two months in Mexico to avoid the winter. We don’t have anything on the calendar yet for next year. If I never spend January and February in Philly again, I’d be fine with this.
This idea for living somewhere for two months. It’s not so much to travel to region. It’s to live there and get work done, but just be in a better place than Philly in winter.
For more travel hacking tips from Travis Sherry, visit ExtraPackofPeanuts.com, listen to Travis’ podcast and follow him on Instagram, Twitter and YouTube.
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COMING UP NEXT
Travel Gift Ideas
2018 has been a year of big adventures for me and Alfred, the globetrotting gnome! Here’s a few ideas (big and small) to help you find the perfect gifts for friends and family. Feel free to add these to your own Christmas list for Santa!
