A Note From Our Founder:
I still remember living out of my suitcase, craving a community of chill, adventurous travelers. Dipaways was built to create that exact space for us.
I also remember watching the light in our travelers’ eyes the first time they truly experienced a new culture. It was pure magic for them, and for me, as the founder, it was magic too. Almost inexplicable.
Things honestly took off faster than I imagined. Suddenly, we were running trips across continents and building a really supportive community. Figuring out how to establish a real, reliable travel company from scratch was no joke. Over the years, Dipaways has seen a bunch of wins, too many to count, and just as many L’s too.
The biggest lesson? Don’t let the ups and downs shift the vision. Let the vision guide what to do with those lessons. Our travelers have been some of the best teachers. They taught me how to slow down, pivot, and stay locked in on what truly matters.
They also remind me to go with the flow. Lost luggage, canceled flights, or someone losing a wig to the sea mid-photo op (funniest thing I’ve ever seen, sorry if you read this, friend). Watching our people move through challenges with laughter shows me that going with the flow is the best way to enjoy the experience.
Then 2020 hit. The entire travel industry shut down overnight, and just like that, we lost everything. Rebuilding while taking care of the people and families relying on Dipaways was pressure. Going with the flow felt damn near impossible.
Thinking back, taking an unexpected two-year break didn’t drown Dipaways, it gave me space to make it work really well. A reminder that readjusting isn’t failure.
If you’re a small business owner, creator, or anyone holding down a vision without the traction you want, understand that’s often what it takes. Keep going.
During that breather, a major television network reached out about a series on Dipaways, and we signed a multi-season deal. We filmed with a top Hollywood production company, feeling like we were on the verge of something massive.
When the network suddenly changed directions, it was a tough pill to swallow, having felt like we wasted nearly two years on it. But no, that wasn’t the case at all. The truth is, a global studio saw enough magic in our little travel company to invest real time and money into us, a reminder that we are building something special. There are always reminders.
Since then, we’ve been building smarter, hosting private experiences, bringing adventurous travelers together on group trips, and tightening operations so it’s all sustainable.
A big part of that magic comes from our local connections. These aren’t just vendors, they’re seriously like friends and a huge part of the family. The heart and craft they put into every detail bring our experiences to life.
Recently, I got back to personally hosting trips after a few years, refreshing my perspective and reminding me why I love this work. I really enjoyed spending time with our groups in San Diego, the Amalfi Coast, Tokyo, Kenya, and Zanzibar.
It’s a real privilege being trusted with life’s milestones: proposals, birthdays, weddings, and family celebrations. Dipaways being a backdrop for these moments is something we’ll never take for granted.
Big love to every traveler who trusted us, my friends and family for showing up when it mattered most, and our local partners for making the world feel like home.
Ten years is right around the corner!
Dricks Everette
Founder, Dipaways