Behind the Scenes of How I Plan a Trip

I'm good at off-the-beaten-path travel.

I think there are so many more authentic experiences to be had with this travel philosophy, so it's something I actively practice prioritizing.

Travel provides the space to delve into the unknown, trust your instincts, take chances, and embrace the unexpected wonders of the world around you. Embarking on a journey is akin to taking a Detour — and Detours are laboratories for our hearts and souls when done intentionally.

When crafting the itineraries for my Dare to Detour retreats, I start by defining what we will NOT do. The point of these trips is that I want it to be a true Detour - not an itinerary you would do with family or your friends. So rather than following the traditional tourist trail or "top 5 must-sees" outlined by popular travel guides, I intentionally opt for truly unique experiences. I will look at Former's or Lonely Planet to point me in the direction away from what our itinerary will be. Instead, I look to current events and pop culture (think "Outlander" for Scotland), local traditions, and nature to guide me. Sometimes, one Google search leads me down the perfect path. Other times I reach out to friends who share a similar sense of adventure and have experience in the region I'm interested in, and get their suggestions. I am drawn to smaller villages and big nature, always, so you can trust that every Detour will safely take you off the beaten path.

For instance, a trip to Scotland typically includes a visit to Edinburgh, St Andrews, and golfing. Aside from flying in and out of Edinburgh, we will be doing none of those things on our Scotland retreat. And that was done intentionally!

As the experiences I want to include begin to present themselves, a theme comes to light that I often center each retreat around. Whether it's a Food and Wine Exploration in Italy or a Walking and Whiskey adventure in Scotland, the theme guides our immersive experiences. We delve deep into the heart of each location, connecting with its culture, nature, and people. In Scotland, for example, we will be learning about the Rewilding initiative of the Scottish government committing to nature recovery across 30% of the land, we will be staying in Cairngorms National Park, hiking daily, and exploring activities that allow us to connect with nature like forest bathing, swimming in a loche, and whiskey tasting of course ;)

Immersion is also a key component to designing a Detour experience. I often choose to stay in one location rather than hopping from town to town, allowing us to sync with the community's rhythm and forge meaningful connections with the locals. This intentional approach to travel opens doors to authentic experiences and cultural exchanges that are often missed when you're constantly on the move or only in a town for 2 or 3 days. After a week in the Dolomites, we became a part of the community's fabric. The whole town knew our group and was excited to see us every day. So of course the family that makes the cheese for the village had us over, of course... That is not something that would've happened if we were there only for a day or two!

Finally, I like to keep my groups small and the itinerary expansive. These retreats are about intentional, unhurried travel. There are no tour buses in sight here; instead, we travel together in a van, creating a close-knit bond within the group. Each day is curated with one or two immersive activities that align with the retreat's theme. And there's ample downtime for personal reflection and relaxation.

At the core of every Dare to Detour itinerary is my belief in stepping out of our comfort zones and fostering genuine connections with ourselves and others. Building itineraries that prioritize immersion, unique themes, and intentional travel practices is my method for creating an experience that goes beyond the traditional tourist route.