The Christmas Trip Nobody's Stressed About: How to Plan It Now
Christmas in a snowy mountain lodge with family
Every year, around now, the same message arrives in my inbox. "We've just realised we haven't sorted Christmas. Is it too late?"
The short answer is that it's later than ideal, but it's rarely too late. You just have to plan a little differently.
Why Christmas away is worth it
For a lot of families, Christmas at home means one person doing everything. The shopping, the cooking, the hosting, the washing up, the relatives on the sofa until New Year.
Christmas away changes that. Nobody has to cook. Nobody has to host. The children wake up somewhere extraordinary, and the adults get to enjoy the day rather than run it.
That's why the best places book up so early.
What you're up against in October
Christmas and New Year are the busiest weeks of the year for the hotels families love most. By now, a few things are usually true:
The rooms that suit families go first. Suites, connecting rooms and villas that sleep four or more are often long gone at the best known resorts.
Many resorts have minimum stays over the festive period. Seven nights or more is common in the Caribbean and in the mountains, which rules out a quick few days.
Flights on the key dates are full or expensive. Especially from the West Coast on the weekend before Christmas.
None of this means you should give up. It means you need to be flexible in the right places.
Where the space still is
Shift your dates by a few days. Leaving on Boxing Day and staying through New Year, or going the week before Christmas, often opens up far more choice. Some families have their Christmas morning at home and fly the next day, and love it.
Look beyond the obvious names. The resorts everyone asks for are full. The equally lovely one down the coast, or on the next island, often isn't. This is where knowing the properties well makes all the difference.
Consider a villa or a residence. A private villa with staff can work beautifully for a family Christmas, especially with grandparents joining. You get your own kitchen if you want to do a proper Christmas lunch, and a chef if you don't.
Think about a luxury cruise. Holiday sailings on the smaller luxury lines can be a wonderful answer for three generations. Everyone unpacks once, the festive details are all taken care of, and everyone can do their own thing.
Stay closer to home. From Southern California, the desert, the coast and the mountains are all a short drive or flight away, with far fewer logistics than a long haul trip.
Get on a waitlist. Cancellations happen, especially in November when final payments fall due. Through my hotel relationships I can often be told when something opens up.
What I'd do this week
If you want to go away this Christmas, start now rather than after Halloween. Decide what matters most: the dates, the destination, or the type of place. You can usually have two of the three this late, but rarely all three.
Then let someone who knows the properties look for you. The difference between finding a lovely Christmas and settling for a disappointing one is usually knowing where to look.
And for next Christmas
If this year isn't going to happen, or you've already booked and loved it, the families who have the easiest Christmases do one thing differently. They book next year's in the spring, or even rebook before they leave.
I wrote about why booking early matters in Why August Is the Best Month to Book Your Winter Holidays. It's never too early to have the best room for Christmas 2027.
If you'd like me to see what's still possible for your family this year, you can work directly with me here.
Quick answers
Is it too late to book a luxury Christmas trip in October? Usually not, but you'll have more choice if you can be flexible on dates or look beyond the best known resorts.
When should you book a family Christmas holiday? Ideally the spring before, and no later than the summer, especially if you need a suite, connecting rooms or a villa.
Where can families go for Christmas at short notice? Villas, smaller luxury cruises, less obvious resorts near the famous ones, and destinations within a short flight or drive of home.
