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For a lot of us, the holidays are an annual rerun. The same week, the same house, the same people, the same small set of obligations. Some years, that's exactly what you want. Other years, you start looking at flights in October.

We’ve been running holiday trips for years, so we know we aren’t alone when we say Christmas Day looks pretty good from a rainforest, a fiord, or the southern tip of Africa. This year, we’re making it even more special with two unique itineraries: South Africa and Zimbabwe, and New Zealand and Australia. 

That tropical rainforest we mentioned? It’s in Costa Rica, which is our long-time holiday favorite and it's still on the trip calendar. 

“What our travelers mention at the end of a holiday trip is how special it feels to spend the holidays with like-minded people and share a meaningful time of year together in a unique destination,” said Brandon Folkes, who has led four holiday trips with Detours. “That combination is what makes these trips so memorable. Christmas dinner becomes its own kind of tradition. It brings the group together to dress up for the occasion and share a special meal arranged by their trip leader. These dinners usually feature several courses of delicious food, a mix of local favorites and familiar dishes from home, blending the comfort of tradition with the flavors of the destination."

If you're set on a white Christmas, start the holidays early. Our first-ever Thanksgiving trip to Argentina and Brazil in late November. Skip the Black Friday scramble, get a week of summer, and still be home in time for the snow.

With that, it’s time to pick your year-end. Each trip is a small-group gay travel experience, built around the holidays we'd want to spend ourselves.

Our 2026 Holiday Trips:

THANKSGIVING IN ARGENTINA & BRAZIL: NOV 20 - 29, 2026

Our first-ever Thanksgiving trip is made for anyone that would pick a day on Ipanema beach over the best Black Friday deal. We meet in Buenos Aires, where the best steak dinner of your life awaits and late-night tango sets the tone. From there, we head north to Iguazú Falls, one of the world's great natural wonders. Once we cross into Brazil, we stay in Paraty, a colonial coastal town, before closing in Rio de Janeiro. Sugarloaf, Copacabana, and the Christ the Redeemer views do the rest. 

HOLIDAYS IN COSTA RICA: DEC 23, 2026 - JAN 2, 2027

This one is much closer than you think. A direct flight from New York, Chicago, or LA gets you to Costa Rica in about 5 hours, which is about the same as a cross-country flight to go home for the holidays. We start in San José, then head to Manuel Antonio for beach days and sleepy sloths along the way. Christmas Day is spent in the rainforest, and New Year's Eve in La Fortuna at the foot of Arenal Volcano. Between the two, we'll zip-line through cloud forest in Monteverde and soak in natural hot springs under the stars. 

Wherever you spend the holidays, we hope it's somewhere worth flying for.