Detours Gay Travel Blog
When the Unexpected Becomes Unforgettable
- Nov 20, 2025
Some of the best travel stories start with a change of plans. A wrong turn, a spontaneous “why not?”, or a chance encounter that turns strangers into friends. At Detours, those are the moments we love. These unscripted, joy-filled experiences remind us that travel isn’t about ticking boxes. It is about connection.
We have never believed in cookie-cutter itineraries. Our trips are flexible, fun, and built for spontaneity. Yes, they are designed to capture the very best of each destination, but they also leave plenty of space for surprises. We set only the essentials, like when, how, and where we move between destinations, and we fill the rest as we go. If you want to see what that looks like in action, explore our upcoming trips.
That is where our trip leaders shine. They are not just guides. They are a vital extension of our team, helping travelers chase what excites them most, whether that is zipping through the jungle or lounging on a perfect beach with new friends.
When you travel with Detours, it will never be about following a script. It is about saying yes to the unexpected. Trust us when we say this. The best memories are often the ones we never planned to experience.
We asked a few of our team and our travelers to share their favorite unplanned moments. Here are their stories, each one a reminder of what Detours is all about: connection, laughter, and unforgettable adventures.
Clay Inglis, Trip Leader: Unplanned Moments from Stockholm to the Valley of the Kings
Since childhood, Clay dreamed of becoming a modern-day Indiana Jones. By the time he started leading trips for Detours in April 2024, he had already explored more than 50 countries and had come closer to that childhood adventure fantasy than most.
But it was a chance encounter during his first year that expanded our team in the best possible way. When he was solo-leading our 11 Days in Scandinavia trip for the first time, the final stop landed his group in Stockholm, where the city pulsed with Pride Week energy.
“I had been to Stockholm once before on a personal trip, so I took the group to a bar I knew from that visit,” Clay says. “Out of nowhere, I ran into one of my friends from back home in Canada. It was a total surprise.”
That coincidence turned into two unforgettable days. Clay’s friend joined the group, taught everyone some Swedish slang, introduced them to local drinks, and led them to his favorite hidden spots around the city. He even added history lessons and plenty of laughs, blending right in with the group.
“The group loved every second of it,” Clay says. “And the wildest part? That same friend later became a Detours trip leader. Jared started leading trips this past May, so an unexpected reunion with a friend ended up bringing another amazing leader into the Detours family.”
While Sweden was all about connection, Clay’s most personal unplanned moment happened years earlier in Egypt. “It was 2013, right after the Arab Spring. I went to the Valley of the Kings, and there were only twelve people there, compared to thousands the first time I had visited.”
Curiosity led him to peek into the gated tomb of Ramesses II. “The gatekeeper told me if I gave him twenty dollars, I could go in alone,” Clay laughs. “He handed me a flashlight, closed the gates behind me, and I spent almost two hours exploring the tomb in total silence. It was my full Indiana Jones experience.”
Two stories, half a world apart. Both unplanned. Both unforgettable.
Laura Robinson, Operations Manager: Kindness on Two Wheels in Sri Lanka
Laura joined the Detours team in April 2025, bringing years of experience as a Backroads Trip Leader to the behind-the-scenes magic that keeps every Detours trip running smoothly. But long before she was helping craft unforgettable experiences for our travelers, she had one of her own on a cycling adventure through Sri Lanka.
She and a friend set out on their first-ever bike trip together, armed with little experience, limited mechanical know-how, and loads of enthusiasm. After bartering for two rentals from a small local shop, they hit the road. Within the first few pedal strokes, they ran into a stubborn mechanical issue that persisted for days.
“We were sitting on the side of the road trying again when a local cyclist stopped,” Laura says. “He told us he had a friend who could help. We were a little nervous to follow a stranger down back streets, but we decided to trust him.”
That trust led them to one of those unforgettable moments. They pulled into a yard filled with bikes, where a husband and wife welcomed them in and immediately began working on the repairs. As they chatted, Laura learned the couple had both been part of Sri Lanka’s national road cycling team.
While the bikes were being fixed, the man who had guided them there climbed a nearby tree to cut down fresh coconuts. “It was such a simple act of kindness,” Laura says. “It reminded me how travel connects us, no matter where we are in the world. Even on the other side of the planet, cycling brought us together.”
Eddie Strube Casas, Detours Traveler: Finding Community in Unexpected Moments
For Eddie, the most unforgettable Detours moments are never about the views or the activities. They are always about the people.
On his third Detours trip, he joined the 13 Days in Thailand and Cambodia adventure. On a busy day that involved flying from Bangkok to Railay, kayaking along dramatic coastlines, and soaking up a little too much sun on a particularly humid afternoon, a member of the group suddenly became unwell.
“We had been strangers just days before,” Eddie says, “but something about being in that culture, the care and the respect that is so valued in Southeast Asia, it just overflowed onto all of us.”
Everyone jumped in to help. Fellow travelers, the trip leader, and even locals working at the facility stepped forward without hesitation. “It felt unusual, but in the best way,” he says. “It was not an obligation. It was sincere care. You could feel how deeply cultural it was. It puts the whole trip into a new perspective.”
Instead of derailing the experience, the moment bonded the group even more. And that sense of connection has followed Eddie on every Detours adventure since.
One memory that still makes him laugh comes from his 11 Days in South Africa trip. “We had our 4 p.m. meet and greet at a local pub, and a couple in our group suggested we all make bow hats out of our cloth napkins,” Eddie says. “Without hesitation, we all agreed. Just like that, we were no longer strangers. Our leader immediately said it would be a great group, and he was right. We loved it so much that we donned bow hats several times throughout the trip.”
Eddie has now traveled with Detours on nine different trips, with each experience reinforcing the same feeling. This is his community.
“It is very consistent,” he says. “I always tell people these are my gay adventure leaders and my happy place. I even tell them that if they do not feel that way at the end, I will pay for their trip. I have never had a bad group. I look forward to them so much.”
That promise is what carries him toward his upcoming tenth journey, which will be 10 Days in Argentina and Brazil next year.
“Mark my words,” he laughs. “After the 4 p.m. meeting in Buenos Aires, we will all be the best of friends.”
Why the Unexpected Moments Matter Most
Every Detours trip has a destination, but the real journey happens between the lines. It happens in the kindness of strangers, in friendships that form faster than anyone expects, and in joyful moments that unfold when no one is looking for them.
These are the stories that define who we are. Not just a travel company, but a community shaped by curiosity, warmth, and a shared love of adventure.
Wherever your next trip takes you, leave room for the unexpected. That is where the memories live.
If you are ready to create your own unplanned moments, explore our upcoming trips and see where Detours can take you next. Adventure is waiting, and the best parts are never on the itinerary.
Explore all of our upcoming trips → 2026 Trip Calendar