Right now I'm working through options for my own family's holiday travel. Thanksgiving and the winter break are both good excuses to swap your usual routine for somewhere new.
We're deep in college tours at the moment, so we're actually looking at schools in Ireland: equal parts campus visits and an actual trip. If you're turning over the same kind of question, here are three other directions depending on what you're after this year.
Where to go in DecemberCold: Quebec City
Quebec City is an ideal festive destination. The old city is walkable in a way American downtowns almost never are: cobblestone streets and stone buildings that feel closer to a small French town than anywhere else in North America. Unlike places that treat winter as something to survive, Quebec City builds its whole calendar around it: markets, lights, ice skating, the kind of cold-weather traditions that make you want to be outside instead of just waiting it out until spring.
Where to go in DecemberWarm: Costa Rica
Costa Rica works for pretty much anyone: rainforest and beaches in the same day, more biodiversity per square mile than almost anywhere else on earth, and an outdoor-first culture that doesn't require roughing it. It's an easy family trip, an easy honeymoon, an easy first international trip for someone who wants adventure without much actual risk.
December is when the dry season starts, though that depends on which coast. Guanacaste and the Nicoya Peninsula turn sunny and land in the mid-80s. The Caribbean side stays wetter and, not coincidentally, less crowded. December is peak season everywhere else, though, so this isn't a trip to book two weeks out. Hotels, rental cars, and tours in the popular spots fill up and prices climb with them.
Where to go in DecemberUpside down: New Zealand
My family spent Christmas in New Zealand two years ago, and we loved it. Even as a Californian, I'd never swum in a warm ocean on Christmas Day before that trip. December there is full summer: long days, warm water, and pohutukawa trees blooming red all over the country, which is about as close as New Zealand gets to a Christmas tree.
One note: January is peak vacation season for New Zealanders themselves, so it's worth booking accommodations and the popular hikes earlier than you'd think for a holiday trip.
Thinking about a holiday trip? Let's talk about it.
Insider infoHow I actually plan your trip
In my career as a theater director, my job was making something happen within a fixed budget and a fixed number of days, then improvising when the plan inevitably encountered a real-life challenge. A show goes up on opening night whether the set is finished or not. So how does that actually translate into planning your trip?
I start broad. When should you actually visit this destination? What do people say you shouldn't miss? What are the quirkier, more specific things to do that don't show up on the generic lists? And what about you specifically: is there some particular interest that should shape the whole trip? (The client who wants to find a bookstore in every city we visit, say.)
Then I get specific. I put the hotels we're considering on a map and check how close they actually are to the places you want to go, because a hotel eleven minutes from where you'll spend your days is a different trip than the same hotel forty minutes away. I build a rough budget against what you've told me you want, and see where that lands. If there are trade-offs to make, splurge here, save there, we work them out together rather than me guessing at what matters more to you.
Then I come back with a first draft itinerary: real choices, but not so many that choosing becomes its own project.
"Rebecca was super communicative and so easy to work with. She responded quickly to my messages and questions, even during the trip. It was one less thing for me to worry about, which was such a relief!"Meena M., Hawaii