Regina Winkle-Bryan founded Bold Spirit Travel after two decades living and working abroad — from Guatemala to Barcelona — driven by a belief that travel is one of the most powerful ways women can build connection and friendship at any stage of life. Her trips combine modest to moderate physical challenge, cultural immersion, and intentional community in some of the world’s most compelling destinations.

Key Takeaways

1. Travel is a community-building tool. The friendships formed on group trips — women who stay in touch and continue traveling together long after returning home — are often what guests value most.
2. The Camino de Santiago is one of the most transformative experiences available to women at a crossroads. Whether facing career change, loss, empty nesting, or simply a desire for something different, the Camino offers unstructured reflection time inside a structure that naturally generates connection.
3. Group travel removes conflict from group dynamics. When itineraries are pre-planned, friends and family can simply show up — no spreadsheets, no arguments, no resentment.
4. Connection is not a nice-to-have — it is a health necessity. Every physician Greg has interviewed over three years of podcasting points to social connection outside of family as one of the most critical and underreported factors in healthy aging.
5. Off-peak travel is almost always better. Spring and fall visits to Europe mean fewer crowds, lower costs, and cooler temperatures — especially relevant as summers across the continent have grown significantly hotter.
6. Nervousness before a group trip is completely normal. What Regina consistently finds is that by the end of the first welcome dinner, women have relaxed into the experience and begun to form real friendships.

Destinations Discussed

1. Camino de Santiago (Spain) — Bold Spirit walks the last 100 kilometers (the minimum to earn the Compostela certificate) over 10 days at roughly 10 miles per day, with luggage shuttled by van. Best seasons: April–early June and September–October. Recommended footwear: Hoka trail runners.
2. Costa Rica — Wildlife-rich and accessible, with monkeys, crocodiles, and abundant birdlife. Groups stay near an active volcano with on-site hot springs.
3. Scottish Highlands — A hiking-focused trip with serious elevation gain, wilderness trails, and a loch cold plunge followed by a lakeside sauna. Begins and ends in Edinburgh.
4. Iceland — A March adventure built around glaciers, geothermal springs, and lava caves. Highlights include glacier hiking with crampons, the Secret Lagoon, the Sky Lagoon, and geothermally baked traditional brown bread. Next departure: March 2027.
5. Greece & Southern Italy — Santorini, the Amalfi Coast, and a boat trip to the island of Ischia (famous for its thermal springs). Best visited May or late September.
6. Japan (in development) — A pilgrimage hiking trip modeled on the Camino experience, planned for a future departure.

Actionable Guidance

1. If the Camino is on your list, start training now — five miles a day, five days a week in the two to three months leading up to the trip.
2. Consider an immersive language course abroad as a solo travel entry point. You arrive with built-in structure, a daily schedule, and an instant peer community.
3. For private or custom group trips of six or more — milestone birthdays, long-standing friend groups, family reunions — Bold Spirit can plan a custom itinerary.
4. Check Meetup.com for travel-focused women’s groups in your area. Regina runs several aimed at connecting women who want to explore together.
5. In Iceland, consider the Sky Lagoon or Secret Lagoon over the Blue Lagoon — equally beautiful, significantly less crowded.

Connect with Regina

Website: boldspiritravel.com

Instagram: @boldspiritravel

Custom Groups: Contact Bold Spirit directly for groups of 6 or more.

Referenced in This Episode

1. Goal Time— Jet lag and recovery supplement developed by previous guest Patti Milligan, Ph.D.
2. The Way (film) — A popular introduction to the Camino de Santiago.
3. Hoka trail runners — Regina’s recommended footwear for the Camino. Boots are unnecessary for the last 100km.
4. Meetup.com Regina uses this platform to run travel-focused women’s groups.