As AdventureWomen celebrates 45 years, two of its leaders are joining travelers on journeys that could hardly look more different.
Some trips are about seeing as much of the world as you can. Others invite you to slow down enough to notice every mile. I’ve found room for both kinds of travel on my wish list, which is why AdventureWomen’s plans for 2027 caught my attention.
The women-owned travel company is marking its 45th anniversary with two trips accompanied by its leadership. Co-owner Judi Wineland will join an 18-day journey through Southeast Asia by private plane. President Paige Davis will take the Portuguese Way of the Camino de Santiago with a group of AdventureWomen travelers.
One trip crosses five countries. The other follows a walking route from Porto, Portugal, to Santiago de Compostela, Spain. They offer two very different ways to share an adventure with other women.
Five Countries, One Private Plane
From November 1 to 18, 2027, Wineland will join the inaugural Exclusive Southeast Asia: A Grand Journey Through Singapore, Indonesia, Vietnam, Cambodia & Thailand by Private Plane.
The itinerary begins in Singapore, continues to Sumatra and Bali in Indonesia, then visits Vietnam and Cambodia before ending in Phuket, Thailand. Along the way, travelers are scheduled to explore Sumatra’s rainforest, spend a night cruising Ha Long Bay, visit the temples of Angkor and enjoy time on Thailand’s coast. AdventureWomen says the private charter is intended to simplify travel between destinations and give the group more time in each place.
That logistical piece matters. Anyone who has planned a multi-country trip knows how quickly airport transfers, flight schedules and hotel changes can eat into the time you hoped to spend exploring. Here, those connections are part of an organized itinerary, leaving travelers to focus on the places and people they came to meet.
Wineland knows the adventure travel business well. She launched Overseas Adventure Travel in 1978 and later founded Thomson Safaris and other travel companies. She and her daughters, Nicole Wineland and Erica Landerson, acquired AdventureWomen in 2016. For this departure, she’ll be experiencing the journey alongside guests.
“Traveling by private plane allows us to spend less time navigating the logistics and more time absorbing these magnificent destinations, their cultures and the company of the women traveling with us,” Wineland said in the announcement.
What to know before picturing 18 days of lounging
AdventureWomen rates this trip Level 1, Easy Pace, but the itinerary still includes active outings. A rainforest trek in Sumatra, for example, is listed at roughly six hours, with its distance and duration adjustable according to guests’ preferences. The aircraft is a privately chartered regional turboprop. AdventureWomen lists the November departure from $69,995 per person based on double occupancy; international flights to Singapore and home from Phuket are not included.
It is a substantial splurge. For someone dreaming of Southeast Asia and drawn to a fully planned, multi-country experience, the appeal is easy to understand: rainforest, cities, temples and coastline in one journey, with a group of women sharing it from beginning to end.
The Camino, One Step at a Time
Davis’s trip takes the opposite approach to distance. She will join AdventureWomen’s September 6–14, 2027, departure of Camino: Hiking the Portuguese Way in Spain, a nine-day journey that begins in Porto and ends in Santiago de Compostela.
The days combine guided walking with time to experience the communities, history, and food along the route. The reward is more than reaching the cathedral in Santiago. It is the experience of getting there together, at a pace that makes room for conversation and for noticing what is around you.
“The Camino asks you to experience a destination differently. at walking pace, paying attention to the landscape, the communities along the way and the people beside you,” Davis said in the release.
I think that last part will speak to many women considering a trip like this. A walking journey gives you hours beside your fellow travelers. Friendships have time to form over a shared climb, a meal at the end of the day or a quiet stretch of trail. There is also the satisfaction of discovering what you can do when you keep putting one foot in front of the other.
This is the more physically demanding of the two trips. AdventureWomen rates the Camino itinerary Level 4, High Energy, and recommends that travelers be prepared for full days of hiking. The company lists luggage transfers between hotels, so participants do not have to carry all their belongings on the trail. The September 6 departure currently starts at $6,495 per person based on double occupancy. International flights are extra.
If the Camino is calling your name, I’d look closely at the daily walking plans and the company’s activity guidance before booking. This is a journey to prepare for, and that preparation can be part of the pleasure.
The Company Is Part of the Trip
I often travel with my husband, but I understand the appeal of a women’s group trip. Maybe your usual travel partner doesn’t share your interest in hiking for days, or perhaps Southeast Asia has been on your list for years, and you are ready to go. Traveling with a group gives you people to experience it with, even if you sign up on your own.
AdventureWomen says many of its guests travel solo and that it can pair travelers who do not choose a single room supplement with a roommate. Its trips are open to women and people who identify as part of the women’s community. Those details may make it easier to take the first step toward a trip you might otherwise keep postponing.
The Southeast Asia and Camino departures are miles apart in price, pace and style. Yet both put time with fellow travelers at the center of the experience. As AdventureWomen enters its anniversary year, Wineland and Davis are joining guests for the part that matters most: the journey itself.
You can explore the Southeast Asia itinerary and the Portuguese Camino itinerary on AdventureWomen’s website. Prices and availability may change, so check the trip pages for current details before making plans.
