15 Highlights from 8 Years on the Road

Three weeks ago, I celebrated my eight-year anniversary of being on the road. On the warm morning of July 26, 2006, I left home for a year-long trip around the world. I didn’t return until 18 months later.

I thought I’d be happy going back to cubicle life when I returned. I’d put my MBA to good use, promote renewable energy, and head down the path towards the American dream (job, wife, house, retirement, etc.). But the moment I sat back down in that cubicle, I realized office work wasn’t for me, and, a few months later, I was back on the road facing an uncertain future.

Now, eight years later, my life is one I never would have imagined when I waved good-bye to my parents. I never even dreamed that I’d be a published author, blogger, and life-long traveler.

As I move into my ninth year of being a nomad, I wanted to share some of the defining moments I’ve experienced on the road:

Living on an island in Thailand
Eating dinner around a candlelit table with travelers outside in Thailand
When I was first in Thailand in 2006, my friend told me to join her in Ko Lipe, a hidden paradise way more beautiful than the touristy Ko Phi Phi I was on. So, listening, I made the then-long journey (now you can take a speedboat) and stepped onto an island that I’d come to call home. On the way over, I met a cranky Irishman, an English couple, and a German couple. I expected to stay on the island three days. A month later, I was tearfully waving my group good-bye as I boarded the boat back to the mainland. We had all become wrapped up in our own version of The Beach, never wanting to leave an island devoid of paved roads and tourists where our days were full of eating Thai food, learning the language, befriending the locals, reading, relaxing, and snorkeling every corner of the island.

While I’ve since grown apart from most of the people whose company I enjoyed on the island (though the English couple and I remain incredibly close), the month I spent on Ko Lipe remains my greatest memory from all my travels.

Teaching in Bangkok
Locals and friendly travelers hanging out at a party in Bangkok
Wanting to stay in Asia longer and needing money to extend my trip, in early 2007 I decided I’d move to Bangkok, learn Thai, and teach English. I didn’t know anyone. I had no idea how to get a job. I had never moved somewhere before. I spent my first week in the city playing Warcraft by myself in between interviews. I remember being bored a lot, wondering if I could really make it in this new environment.

But as they say, it’s always darkest before the dawn, and just as I was thinking I’d made the wrong decision, a friend from home gave me the name of someone living in the city. My friend’s friend and I met for drinks, and he introduced me to the expat social scene in the city. Shortly after, I got a job and a girlfriend and began to build a life in Bangkok. I learned to take care of myself and live on my own.

The months I spent there helped me become independent and showed me I could start a life anywhere.

Moving to Taipei
Famous gate in Taipei, Taiwan lit up at night
In many ways, moving to Taipei in 2009 was a failure: I met a girl who dumped me right after I decided to get a long-term visa to stay with her, I got the flu that never went away and lost about 15 pounds, I had a job I hated, and I never thrived the way I did in Bangkok. But it was also a huge success because it was during that time that I decided to make my blog more than just a hobby and focus on making it a resource for travelers. Those were the months that I started turning my year-old blog, whose original purpose was to keep my friends updated on what I was doing, into the travel resource it is today.

I might not have thrived in Taipei, but I’m also not sure, had I not moved there, that this blog would even exist. I’d probably still be an English teacher in Bangkok.

Playing poker in Amsterdam
Fun friends posing together in Amsterdam
During my first trip to Amsterdam in 2006, I walked into a casino to play poker. I befriended some other players, and, after heading to Barcelona a few days later, decided to fly back to Amsterdam—I missed it too much to stay away. For the next three months, I played poker every day with these guys. They showed me the city, introduced me to Dutch culture, and became my first international friends. It was the first time I really connected with locals, and, when I finally had to leave, I thanked them for opening me up to new experiences and told them I’d see them the next year. A few months later, I learned our friend Greg was shot while people tried to rob his house. Greg was the one who first invited me into their group. I never got to really thank him, but I’ll always remember his influence on my life.

Visiting Africa
Watching the colorful sunsets in the African desert was a great experience
Going on safari in Africa had been a life-long goal of mine, and the weeks I spent exploring the southern part of the continent in 2012 were everything I had hoped they would be—wildlife all around me, stars lighting up the night sky, fiery savannah sunsets, and raw and beautiful nature. The sights, the can-do attitude of the locals, the wildlife, the food—Africa was better than I had imagined. It was raw, unfiltered, and is burned into my soul.

That continent truly is magic.

Hiking the Tongariro Crossing
Picturesque view of the blue Tongariro Crossing in New Zealand
One of the most famous hikes in the world, the Tongariro Crossing might be recognizable to those who love The Lord of the Rings as the location of Mount Doom. Tackling this 22km hike was going to be a challenge, as I’m not a fast hiker and I was out of shape at the time. I started early in the morning, befriended a fellow hiker along the way, and together we barely made it as the last of the buses back into town pulled away. It was harder than I expected at parts, but I made it and that day in 2010 was the most rewarding I had in New Zealand.

Learning to scuba dive
Two men scuba diving in the reefs of Fiji
Learning to dive in Fiji was one of the scariest moments of my life—I almost died doing it. During my third dive, my partner kicked the regulator out of my mouth while we were below the surface looking at coral. I acted quickly and breathed out, grabbing the second regulator in a panic as my dive instructor leapt (or bolted like a fish) towards me. I stayed there, breathing heavily while I tried to calm down and managed to swim for a few more minutes before ascending to the surface.

It was a scary moment (and my dive partner never did say she was sorry!), but it didn’t ruin my love of the ocean. I got to see a whole new side to life on this planet, and I’ve been hooked ever since.

Throwing tomatoes at La Tomatina
Friends posing together in Spain happily
Throwing tomatoes in Spain was exactly as fun as it sounds. Waking up early, riding the train, drinking sangria, and pegging people for an hour with tomatoes was a once-in-a-lifetime experience (as in, after doing it once, I’m OK not doing it again). But I owe everything to the Nest Hostel in Valencia. Their policy during the festival stated that you needed to stay for at least a week, and our little group of hostel guests became like a family. Surrounded by the same people in the hostel, you got to know everyone in a way that usually doesn’t happen. But that family became even tighter as the five others in my dorm room and I bonded throughout the week. We hit it off like we had known each other for years (which many people assumed since we were so close). After the festival, we kept traveling together, and, five years later after that fateful week in 2009, we all remain incredibly close and connected.

Surviving Oktoberfest
Matt Kepnes posing with 4 huge beers at Oktoberfest in Germany
When we were planning our trip in 2011, my friend Matt and I decided five days should be long enough to experience Oktoberfest. We were seriously mistaken—a couple of days is enough, and by day three, we were waving the white flag. We somehow managed to power on, and, dressed in lederhosen, we ticked a life-long goal off of both of our lists. It was incredibly fun, and I met some wonderful Germans, ran into friends I already knew, and learned that after four steins in a row, I will pass out fall asleep at a table.

Discovering Eastern Europe
Beautiful buildings at an old town square in Eastern Europe
When people ask me where they should go in Europe that’s a bit out of the way, I recommend three countries: Bulgaria, Romania, and Ukraine. A few years ago, I backpacked through these countries and fell deeply in love with all of them (especially Ukraine). They were a new experience—more rustic, less touristy, seemingly still twenty years in the past, and overall, a completely different feeling than Western Europe. They were challenging to navigate—I had to pantomime in Ukraine to get around. They were super cheap. The people were friendly and welcoming. One of my best memories is drinking with some Ukrainians who only knew the word “cheers.” We couldn’t communicate, but we bonded over many shots of vodka.

Connecting on the island of Ios
Posing with local Greeks and traveling friends on the island of Ios
Continuing the theme that people make places, in 2010, I decided to visit the island of Ios in Greece. At this point, I don’t remember why I initially decided to go, but I somehow found myself there. And, as with Ko Lipe, I ended up staying longer than planned. A group of us on the island bonded instantly. They had come early in the season to find work (they all did), and I had nowhere in particular to go, so I stayed. We were like a family, meeting up for nightly dinners and outings around the island. The following year, we all came back and picked up right where we left off. Even though we are now spread out around the world, I’m still in contact with most of them on a regular basis. Time and distance don’t destroy deep friendships.

Discovering Coral Bay
A view of Coral Bay in Western Australia
Driving up the west coast of Australia, I pulled into a tiny beach town called Coral Bay. It’s a one-street town with one hotel, one bar, and one supermarket. Most people come here via camper van and stay in the RV park. This place is heaven; it’s my beach paradise. The Ningaloo Reef is so close to the shore you can swim to it, the water is crystal clear, and marine life swims near the shore. I’ve found my way to this out-of-the-way destination twice, and it’s my favorite place in all of Australia.

Visiting the Galapagos Islands
Orange sunset in the Galapagos Islands
I knew the Galapagos were beautiful, but everything I had heard about them underestimated their beauty. The land, the sea, the sunsets—words can’t describe them. Pictures can. (Lots of pictures.) My time spent on the islands can be summed up by my last night: the boat was moored while we ate dinner with the spot light on the back. Fish attracted to light swam in the area and then suddenly, seals began to dart back and forth. Later, as we made our way back to Santa Cruz to leave in the morning, dolphins rode our boat’s wake for over twenty minutes, playing and jumping in the sea. It was breathtaking. Just like the islands.

Hiking the Grand Canyon
Amazing photograph of the Grand Canyon in the USA
During my cross-country road trip in 2006, I fancied myself a hiker (I wasn’t) and was determined to hike to the bottom of the Grand Canyon. Rising early one morning, I drove with my hostel dorm mate to the park, stopping to watch elk graze nearby. After pulling into the parking lot and marveling at the view, we escaped the coming tourist crush and became part of the small cadre of visitors that go beyond the canyon ridge. We hiked down to the base and spent a night before hiking back up. Along the way, we stopped in a stream to cool off, and we made it to the top of the canyon just in time for one of the most beautiful sunsets I’ve seen. I distinctly remember the sense of victory that rushed through me as we reached the summit.

As a Gemini, I’m fickle. I don’t often stick with things long. But six and a half years later, here I am, still sharing my stories on this site and helping others travel more. And it’s all because of you. This website, more than any trip, has changed my life. I’ve met some of my best friends because of it, and hosting meet-ups and reading your emails inspires me to be better at everything I do. I wake up thankful everyday that I get the chances I have, and it’s all because of you.

The last eight years have left me with more happy memories than I could ever write down in one blog post, and while every memory is important, these moments have defined the last eight years and led me to where I am today.

To quote my favorite movie, American Beauty:

“…but it’s hard to stay mad when there’s so much beauty in the world. Sometimes I feel like I’m seeing it all at once, and it’s too much, my heart fills up like a balloon that’s about to burst…And then I remember to relax, and stop trying to hold on to it, and then it flows through me like rain and I can’t feel anything but gratitude for every single moment of my stupid little life.”

  1. Oh wow. I am gonna cry. So happy to read all of this and so much hoping to become brave enough to take my steps toward the dream coming true. I am starting with my blog, quit my apartment and step by step I’ll get there too. Can’t wait!!!! <3

  2. theveldtrekker

    Sooo glad i took the step of moving to south korea in june this year!! And I can’t wait to join one of your meetups bro!!! Going to be epic!! I’ve been on vacation in Nepal for just over a week! Met so many people who are just so in love with travel!! It’s very inspiring :) i will never settle for an office job

  3. D.

    I LOVE travelling, but nothing is ever as lonely as travelling…. I’m so jealous of people who can build relationships quickly and bond with pretty much anyone, for me it’s a struggle just to function at basic conversation level. I wanna go back home not because of the work and my crappy everyday life but because my few long-term friends are there. I wish I could be someone else….

  4. So inspiring! I did a post like this remembering my past year in Brazil, sometimes it’s good to write down your best memories in one place. Also, I hope I’m still traveling after 8 years, only time will tell!

  5. Absolutely amazing how many cool things you’ve done! I haven’t done anything on your list of favorites except scuba, and I almost died too (well, not died…) After how many countries I’ve been to and living in India for so long, reading this reminds me it’s the THINGS you do while you’re abroad that really count, not just seeing somewhere. THanks for the kick in the butt to get out there and try some new things in new places!

  6. It looks like you picked some good memories Matt, but I still personally think that having tomatoes all over you and tomato’s juice on your skin isn’t the best, perhaps if I try myself I’ll change opinion :)

  7. What an amazing 8 years! Eight years travelling, that’s incredible, sure as hell beats working in an office every day eh. I didn’t know you’d been to Coral Bay. I worked their for three months. It really is stunning, although a little too remote for a three month stay!

  8. Matt, I loved this post. Your reflections are honest and inspiring and you’ve really had quite the journey over the past several years! Your site was incredibly helpful when I finally decided to take the plunge, quit my job and start prepping for a five-month adventure. Your photos are gorgeous and I’m glad you take the time to get to know locals everywhere you go! Something that’s definitely shaped my travels yet overlooked by many travelers. Keep it up, man.

  9. Nice to read about Coral Bay… I was there in 2006. Planning to stay they for 1 night.. to dive to the reef… but stuck for 2 more days because an incoming cycloon… no diving,.. really nothing to do. But finally was with the first divers after the cycloon which was a great experience…

    BTW.. I learned to scuba dive just months before while volonteering in the Philippines…

  10. Wonderful inspiration! At the end of the day though, much of what you appreciate through travel comes from the company you keep, and its wonderful to see how you’ve bonded with so many people on all your journeys.

    It’s been great bonding with you over your website as well. And if you’re ever in Singapore again, do give me a shoutout! =)

  11. Wow. Amazing stories from so many beautiful years you spent on the road. Very inspiring, and I also really love the quote at the end, it reflects well what I feel when I travel. Keep enjoying traveling with many more special moments!


  12. Karen Shakespeare

    Coral Bay is my favourite place in Australia as well. We were travelling around Australia & spent a couple of years in the Pilbara, so Coral Bay was our long weekend escape. I am so jealous, in a good way, of how much you have experienced. I am travelling around SE Asia and heading to Nepal for my birthday in a couple of weeks. I don’t wanna go home!

  13. I’ve learnt to love scuba diving too… although i’m a scaredy cat still. Need to spend a few months dedicating myself somewhere wonderful, to the experience!
    It must be amazing to do what you have done – as a mum of two adult children 21 &19 (The 19 is in Divemaster training on Koh Tao at the mo! There are so many amazing places to visit and things to do – haven’t quite figured out how to earn money to enable me to do them yet but
    am working towards it.

    New Zealand is the most amazing place to walk. I liked it very much and thought it ideal for a self drive holiday with children – oohhhh this has just inspired me to write a new post about the very subject above. Thanks Matt!!!

  14. inspiring! how you summed up such a great lifetime of events in one article is beyond me, this could not of been an easy post to write, but I bet you had fun reminiscing. Your adventures, just briefly described are so inspiring to know there is so much to look forward to in life! loved reading this :-)

  15. Great post. You’ve really come so far but the best is to know there are MUCH more to discover :). I particularly enjoyed on how you lived in an Thai island, sounds amazing!
    Keep up the great travels!

  16. An amazing compilation of how wonderful the last eight years of your nomadic life have been. Obviously, there must have been a number of ups and downs, but when connecting the dots backwards, it looks like a perfectly scripted adventure story;-) Superb Matt! Your post is an inspiration for bloggers like us to keep going and to be at it!

  17. This gave me goosebumps! So wonderful. You were my first travel inspiration after I bought your how to travel the world on $50 a day book. My boyfriend and I leave on our year long adventure to Australia (and beyond) in a week!! I also used your e-book on blogging to help build my website! Thank you so much for your advice, you are such an inspiration!!!

  18. A huge congratulations for all your achievements Matt. I’ve been following your adventures for a long time, you travel the way I like to as well it always seems. I also lived in Amsterdam on and off for quite a while, and played poker at the casino there as well as underground games to help fund my trips. In fact I am leaving Amsterdam today for Kyrgyzstan after visiting friends for two weeks. I got a good poker game in last night! All the best for the future. I still haven’t figured my own future yet, I left home back in 1997 and have been living and travelling overseas for the past 17 years.

  19. Wow Matt! This is so inspirational. I just turned 23 today and I can’t wait to start living my life the way you’ve lived yours. I am a gypsy at heart, and I can’t wait to travel the world, and meet beautiful people, and make a difference. I truly hope we cross paths some day!

  20. I love that you bring up your fickle Gemini nature…me too! Hence why I think exploring is such a good idea, I suppose…the only constant is change. Thanks!

  21. Kimberly

    After my job took me to live in Finland for 6 months, I thought that would satisfy my hunger to travel. Wrong! It only whetted my appetite even more. Even the few days in Amsterdam , Berlin , Munich , and northern Italy weren’t enough.
    Like you, Matt, when I returned to my cube job, I knew I don’t belong there anymore. So early next year, I chuck it all and head over to Europe. At the age of 51, it certainly isn’t the normal path, but being Abby-normal is truly living. :) Your book has been a great resource for planning. I’ll keep it with me along the way.
    Happy Trails!

  22. Trish

    LUV it! I wish I had done that when I was young……it’s still my dream, though. Your blog is always informative and entertaining. Thanks so much!

  23. Jim Rockholt

    What wonderful reading about your travels all around the world Once you start it is hard to be settled. I still work at 55 but every chance I have I want to be traveling. Have been to Hawaii several times as well as Las Vegas and New York City and cannot get enough of them. Also hope to see Washington DC and Florida as well as other numerous places in United States as well as abroad in later years. Thanks for your blogs, keeps me encouraged that anything is acheivable in life, Best of luck to you Matt.

  24. BlackNProud

    It would be nice if you actually mentioned the country(ies) you visited in Africa. #Africaisnotacountry #fiftyfourdifferentcountries #withthousandsofdifferentcultures

    • Stephano

      He did mention Southern Africa, if you’ve been following Matt for a while you would have read how he did 3 border crossing in a day, Namibia, Botswana and Zambia. Yes Africa is not a country and it gets me upset too but in this case, he kept it to his once off packaged trip in summary

    • NomadicMatt

      I know Africa is not a country but I was describing my entire three week trip there so I included the trip as a whole as “My whole trip to Africa was amazing.”

  25. Stephano

    Amazing how I read about the less well known touristy places you’ve been to (ie skipped over Ios in particular). After being semi-nomadic myself over a similar period of time, Ukraine is also one of my favourite places and laughed how you described it because it is for that same reason I tell people why I love it (got stuck in 1950s Soviet style)… As for the future, keep inspiring us.

  26. Having been fortunate to have traveled a lot in my life, I am gearing up to begin some new adventures. I’ll be retiring in March at the age of 62 and can’t wait. I agree that the key to traveling alone is to reach out and meet other people….regardless of their age…

  27. Jewel

    Matt, love your post. You are amazing. I am trying to get a group together for a trip to the Rioja region of Spain. Any tips on how I can do this? How do you overcome the steep upfront fess associated with the tours and hotels?

  28. Hey Matt,
    I want to tell u that i enjoy reading your weekly newsletter! One of the few emails I don’t delete. You have made me feel Connected to a community of fellow travelers. Really, tour words inspire me to get out there and explore, and keep at it even when you start to get the travel blues. Congrats on eight years and thank you!! Its Also nice to see people nice things on the commentary space, yay positivity. Look forward to your next post(-:

  29. Ed

    You and your site were a HUGE inspiration for my 1-year RTW trip in 2012. I’ve been back for a year now, wishing everyday that I could go out and do it again, but not knowing how.

    Thank you so much for your inspirational content and amazing advice. Looking forward to seeing how you and your site inspire us all in the future.

  30. Mo

    Well Matt, at 51 I am about to embark on a 10 month trip through S America, New Zealand, Oz and Southeast Asia, alone. I have my back pack stuffed, my inoculations done, my house rented, my job on hold and my friends and family lined up for a farewell bash tomorrow night. Never travelled alone before, not even on vacation! But, hey, I reckon if my students can do it, so can I. You have been a true facilitator and a constant source of support. Thank you and please wish this adventurous woman an eventful, joyous and life changing journey. Bless you Hun. Xxxxx

  31. Hi Matt! What a journey! Both ups and downs, with the privilege to see many amazing people. I have not travelled as long as you, just for 4,5 years now.. I really enjoy reading about your travels, getting inspirations of places I would like to visits and some tips. Thanks!

  32. Julia


    Just wanted to say that your blog and newsletters keep my travel bug alive! I traveled the world for years with my family through small vacations but my latest month long trip to Europe changed my attitude and appetite towards traveling. Even though I’d love to drop everything and travel the world I’m not brave enough and so very soon I’ll start my cubicle job. But no need to feel sorry for me! My job will help me pay my student loan, grow as a person and in couple of years I’ll have the great opportunity to travel and relocate with my job. But one thing is for sure, from now on, a portion of every paycheck will go towards saving for a short yearly trip/vacation (and yes, I’m signing up for a travel credit card).
    Today, I can’t imagine a life without traveling the world at least once a year!

    Thank you for all the helpful tips, I’ll sure use more of them in my next trip.

    Enjoy Europe!


  33. Beautifully written, Matt..! Amazing how you made long-lasting friendships through travel.. it really is about being able to stay somewhere longer. That captures it all – you get to really familiarise with the location, befriend fellow travellers and often even locals.
    What’s your view of the future? Do you think you might become a life-long nomad?

  34. Addie Morton

    Gratitude is one thing you can never take back. Well done. This is inspired, and rich with memories. No movie can capture the highlights of your life. You have to write them.

  35. Sumit Pawar

    Their is no substitute for great memories. When are going to visit Mumbai and India.
    Thanks for inspiring me to travel.

  36. Devlan Miller

    Great stuff! Truly lights a fire under my ass to get moving and start exploring the world. Matt, you’re a BMF! Cheers!

  37. What a wonderful and inspiring reading! Can’t wait to read what kind of memories you have made by 2023. Just keep up the good work what you’re doing, and keep us updated with your super awesome and inspirational stories. Thank you for inspiring me. :)

  38. Lori

    Tongariro crossing remains, to this day, one of my fondest memories of traveling, especially since I completed it with my 53 year old father on his first trip out of the United States!

    I’d say perhaps buying moonshine with the group of people I met at my hostel and kayaking through the biobay in Puerto Rico is up there too.

    But, I’d have to say, the one thing that all the best memories have in common are a) doing something you never imagined you could and b) sharing the experience with an incredible group of “strangers” turned best friends within hours.

    I came across your site before I started traveling two years ago, and I could have never even imagined how much it would change my life. From the people I’ve met to the experiences I’ve have to the new foods I’ve come to love and miss and cultures and language barriers. Also, being able to thrive and survive outside of my comfort zone has been so inspiring. Traveling has made me more open minded and compassionate, and really given me a sense of purpose in life.

    I have encouraged and helped plan trips for fellow students who don’t think that they can do it (due to money, time, etc.) and have used your site to help guide and inspire them. I also never thought my dad, who is my hero, would ever let himself take a vacation and actually enjoy himself for a little while rather than always focusing on working and supporting his family.

    So thank you Matt, you have no idea how much you have helped me and my family and friends. I hope you continue to keep on in your travels and change lives every day.

  39. Sharaj

    Thank you Matt! You are an inspiration. I have been travelling for few years now but nothing really great. Also i started following you since few months. Now, thanks to you I am going on a solo trip to Mexico tomorrow!
    Thank you.

    Take care Matt.

  40. So many amazing experiences! I actually hiked the Grand Canyon when I was in 8th grade, but I’m dying to do it again as an adult, and explore different parts. Amazing Post!

  41. Brynne

    Wow! I’m only in my freshman year of high school, and I’ve always known I want to travel, but you’ve convinced me to backpack around the world at the first chance I get! Thank you! :)

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