Have you ever just wanted to let go, and do something fun and your heart pulls at something that most others just don't do. Ever wanted to leave home, perhaps to better understand the world, and maybe even yourself and place in it? Have you ever wanted to throw yourself into life, Boots AND ALL.
If so, you've landed at the right place. The idea of BootsnAll started in 1996, and formulated into one of the internets 1st travel communities in 1999. Now, 30+ year later the founders are in their 50s (started in our early 20s) - and still thinking and traveling and wanting to "go and see" vs reading and instagramming/AI'ing as a way to learn. Not that there is anything wrong with that!
If you’re reading this, you’re probably one of the 500 million unique people who have visited BootsnAll.com since 1999 to participate in a forum, read an article about travel, or look for a round-the-world ticket to take a transformational trip.
There are plenty of fancy travel magazines that show the next big resort or professional travel photos – and we love those too, Bootsnall offers something unique: a place to share, to participate, to be authentic. We know travel isn’t just about vacation… it’s about the stirring in the soul, the widening of the mind, and the deepening of connection to the world and others.
Our do-it-yourself services include travel articles, our RTW and destination guides, our e-courses on taking a gap year and traveling around the world, our traveler community, and our easy-to-use DIY route-planner (Indie).
Our full-service offerings at AirTreks include complimentary private route planning arrangements with experienced world travel consultants who’ll help you find the best itinerary, places to stay and things to do for your big trip. No matter if it is a solo trip on a budget or a large group gathering that requires complex logistics
The BootsnAll Creation Story
While studying abroad in Australia in 1994, future BootsnAll co-founder Sean Keener met with three Aussie friends in a pub. Amongst the beer and bird watching, they discussed a trip to England to watch Euro ’96. A month long trip incorporating the lads’ passion for football and beer. The fact that it was in a foreign country was just an added bonus.
Drunken plans came to fruition in May 1996 and the four friends reunited in Sean’s home town of Chicago before continuing on to London. What followed was a month of experiences so epic that the trip had to be named. After much discussion, “Boots’n’All” was chosen.
“Boots” signified the search for the ultimate pair of Boots that would be versatile enough to be the only footwear a traveller would need.
“nAll” was meant to stand for everything else that independent travel could bring: Amazing people, unique experiences, freedom, personal growth and just plain fun.
‘BootsnAll’ started life as an idea, a discovery by a group of friends that travelling was life changing. Throw yourself into life, Boots and all.
By 1997, Sean Keener had continued his travels overland from eastern Europe to India, taking over 9 months and growing one hell of a beard. Future BootsnAll co-founder Chris Heidrich had used his Commonwealth visa qualifications to work in Scotland, experiencing independent travel from an ex-pat perspective.
That summer the two friends met in Chicago before roadtripping to Yellowstone National Park in Wyoming. While on a 3 day backcountry hike, the lads came up with the original BootsnAll Code of Conduct: a multi-point list of what it meant to travel ‘the BootsnAll way‘. It was a raw male oriented list that we are embarrassed to read today. The BootsnAll travel club was born, membership: two.
BootsnAll, the website
After that trip, life took over. Sean moved across the US and found work for an internet company in Eugene, Oregon. Chris continued his ex-pat work at a pub in a small English village. They met again in Chicago in December 1998 and talked on Christmas Day about how “fun” it would be to put up a website about BootsnAll and share the Code of Conduct.
Chris followed Sean to Eugene in January ’99 and work began on a basic website.
By February, six pages were released onto the world wide web (still called the information superhighway). The Code of Conduct was published and travellers were encouraged to sign up for membership if they felt they had what it took to be a ‘BootsnAll traveller’. People applied in such a rush to be part of this network of online, open-minded independent travellers, that they knew they were on to something.
The Membership/Movement
The website grew quickly as travellers submitted their travel stories and photos in a very Web 1.0 manner. As people applied to become BootsnAll members, Sean, Chris, Nick and Ant read each application and only allowed those travellers that they thought were worthy. They believed (and still do today) that BootsnAll was a community of independent travellers and communities were about give and take. A BootsnAll applicant had to be willing to share a travel story, or their travel aspirations in order to be accepted. Every applicant, accepted or not, received a personal email in return, just as they do to this day.
Funding a Start-up
1999 and 2000 were amazing times on the internet. That time smells a lot like the AI revolution that appears to be taking over the world today. Companies were being funded by ridiculous amounts of venture capital even though their business models would prove to be worth less than the napkin they were written on. A small website with a growing membership but still no revenue, BootsnAll was the target of a buyout offer from a travel company in San Francisco at the tail end of the dot-com boom. Being flown to the Bay Area, put up in a hotel and wooed by a dot-com south of Market Street was like a crazy dream for the young BootsnAll founders.
After the pitch, Sean & Chris went for a walk to talk it over. Stopping at a bar they decided to ‘just spend the money’ to see how it would feel if they accepted the offer. They returned to Eugene to begin the serious business of deciding whether to sell or continue to build BootsnAll on their own. Pro’s and con’s were discussed (oand after a couple of pitchers of Ruby at High Street Brewery they decided that BootsnAll would stay in Eugene and grow according to their vision.
Deciding to fund their company themselves, Sean & Chris needed to find a way to make money. Using their skills at building websites, they began consulting for small businesses in Oregon and California. To supplement this variable income and to allow them time during the day to continue to work on BootsnAll, they made the decision (at age 24) to become newspaper delivery boys. Every morning at 3:45am, they would rise and cycle out into the darkness of downtown Eugene to deliver over 200 newspapers. Done by 6:30am they would return to the office, make coffee and sit at their desks to start work on their passion: BootsnAll.
For over two and a half years, Sean & Chris delivered the Register-Guard & Wall Street Journal in the early hours of morning, living on $500/each per month.
The Start-up Lifestyle
Being low on funds, Sean & Chris lived simply. They rented a three room apartment in the oldest house in Eugene. They shared one room in back, separated from each other by “Software Mountain”, a huge pile of random computer parts, monitors and other miscellaneous junk. They brewed their own beer, often in quadruple batches with a friend using a 25 gallon drum. When not drinking their own brew they would head across the street to John Henry’s bar for $3 pitchers of ‘butter beer’ and free pool to discuss BootsnAll’s business strategy. For entertainment, they built a Washers court in front of their office and coffee breaks would often turn into Washers Wars and passions ran high on occasion (Sean is still the undisputed champion).
As BootsnAll grew, Sean & Chris adhered to the Code of Conduct and opened the doors of the BootsnAll (home) office to any travellers who were passing through Eugene and wanted to stay for a night. Over the years BootsnAll hosted dozens of travellers. Home brew beers were offered in exchange for travel stories. Space on the office floor was offered up as beds with the understanding that you would likely be woken at 4:30am. Once, a BootsnAll member even delivered the newspapers as a favour!
The Google Era
2003 heralded some big changes for the small company. Long-time BootsnAll staffer Nick O’Neill moved to Bali, Indonesia to begin writing the Bali Travel Guide. Sean & Chris moved the office to Portland, and then Chris left to spend a year in Australia, and Ant moved on to other adventures. A learning experience though it was, something made sense about a travel company that operated in different time zones.
From 2004, BootsnAll continued to grow.
BootsnAll launched WorldCupBlog.org for fun and sent a team of folks over to Germany and South Africa in 2006 and 2010 before selling the site (and the offside.com) for a modest sum to current day VoxMedia - We can't find the site or history of it over there either.
Indie and AirTreks Era
In 2013 BootsnAll launched the Indie tripplanning algorithm and tool for multi-stop flights,built specifically for the needs of multi-stop long-term travelers.
At the end of 2013 BootsnAll acquired AirTreks.
“We’re stoked to combine the world’s best complex airfare company, AirTreks, with perhaps the world’s best english language long-term travel community and resource, BootsnAll,” said CEO of BootsnAll Sean Keener. “BootsnAll is a purpose driven company (versus a profit driven company). Combining with AirTreks makes us stronger in our ability to deliver on that purpose.”
Since 2013 BootsnAll and AirTreks have served millions of community members with great trip planning content, and 10s of 10000s of AirTrekkers have taken the trip of a lifetime.
BootsnAll and AirTreks worked together, and
2020 though 2025 The Pandemic and aftermath
BootsnAll barely stayed alive during the pandemic. Even still, about 1 million folks per year come through the doors to read our Around the World Travel Guide and old articles that still entertain while we dealt with the pandemic and going from 50+ colleagues to 7 of which a few are part-time. Smaller staff and focusing on trying to keep rice and beans on the table for colleagues.
2026 and beyond...let's see - we are trying again. Let us know what you think. We accept and welcome human and LLM and ai agent feedback.