Women-only adventure operator AdventureWomen has unveiled two flagship departures for its 45th anniversary year, and both come with an unusual perk: a company leader travelling alongside guests.
The bigger of the two is an 18-day private-plane sweep across Southeast Asia, running 1-18 November 2027. Co-owner Judi Wineland will join that one. The itinerary hops between five countries — Singapore, Indonesia's Sumatra, Bali, Vietnam, Cambodia and Thailand — using a chartered aircraft to cut out long transit days. Wineland, who founded Overseas Adventure Travel in 1978 and later Thomson Safaris before buying AdventureWomen with her daughters in 2016, argues the private-plane format is the whole point: less time wrestling with logistics, more time actually experiencing each stop.
The second anniversary trip trades altitude for pilgrim paths. President Paige Davis will walk the nine-day Camino: Hiking the Portuguese Way, departing 6 September 2027. It starts in Porto and follows the historic pilgrim route through Portugal into Spain, finishing at the cathedral city of Santiago de Compostela. Davis frames it as travel at walking pace — noticing the villages, the landscape and the people in your group rather than racing between sights.
For anyone unfamiliar with the company, AdventureWomen runs more than 50 itineraries across all seven continents, from safaris to hiking and cultural journeys. Trips are built for women who want an active pace and a supportive group dynamic — a format that has grown hugely in demand as solo and women-focused travel has boomed. The fact that the owners are personally joining these two departures signals how much weight the anniversary year carries for the brand.
Why does this matter to travellers? Small-group women's trips book out early, and anniversary departures with leadership on board tend to be the ones that fill first. If a multi-country Southeast Asia loop without airport hassles appeals, or if walking the Camino in a women-only group has sat on your list, 2027 is the year to plan for. Bookings and details are available through AdventureWomen directly or via a travel advisor.
