When Should I Actually Book?
A Calendar for People Who Hate Overpaying
This week I’ve been working on booking our flights to Montana for March. Family home, close friends, six months out. The fares were reasonable and the seats were good, easy peasy. (My kids have started asking "So... can we come too?" We'll see.)
Coincidentally, a friend texted: "Thinking about a ski trip over Christmas. Can you help?"
I can always help. But here's what I told her first. Holiday weeks run about three times the price of the week on either side. A proper ski resort over Christmas can hit $30,000 for a family for the week, and that's before anyone buys a hot chocolate. It isn't a scam. It's math. Everyone with a school calendar wants the same seven days, and the mountain knows it.
Her trip needed to be booked in July. Mine, for March, only looks smart because I've been that friend. I've paid the Christmas price. I've stood in a lift line so long I questioned the whole sport. The only difference now is that I finally wrote the calendar down.
So here's the calendar I use. It's not about finding deals. It's about not paying the everyone-else price for the trip you were going to take anyway.
The calendar
Christmas and New Year's: book by July. Earlier if you can. This is the most expensive week of the year almost everywhere, and the good places are gone by late summer. If you're reading this in September and haven't booked, either go the week after New Year's, or pick a destination nobody's fighting over.
Ski season: book by summer, or skip the holidays entirely. Our family rule is simple: no skiing over winter break. We go in March insteadWe go in March instead, when the snow is softer, the lift lines are shorter, and the same condo costs a third of what it did in December. If the holidays are your only option, book by July and brace yourself.
Spring break: book at least six months out. The trick most people miss is that "spring break" is actually a six-week spread depending on the school. Find the week that isn't yours and go then.
Summer in Europe: one year out. Not a typo. Last week I was putting together a few nights in Barcelona for July 2027 and had a hard time finding a refined hotel that wasn't asking a ridiculous number. July and August in the big European cities are the holiday week problem stretched across two months. Book the year before, or go in May, June, September, or October, which is what I'd send you to do anyway.
Summer at home: it depends what you're chasing. We try to avoid heavy travel in the packed summer months, but that rule just got renegotiated. My son went back to school, so we're back on the summer vacation schedule for a couple of years, and I currently have a dude ranch on hold for next summer, hopefully before the crowds come out. Ranches, national park lodges, and anything with a limited number of rooms and a view book out nine months to a year. Beach houses, less so.
The LOOPHOLE: spring skiing
If you missed the ski window, this is your reprieve. March into early April brings milder afternoons, fewer people, and normal prices, as long as you avoid the common spring break weeks and Easter. It's the version of skiing where you finish by two and après-ski on the patio in a light long sleeve. Honestly, it's the better version.
The rule under all the rules
The busier the week is for everyone else, the earlier you book, or the more happily you go a week later. That's it. The date you book matters almost as much as the date you go.
Tell me where you're thinking and when, and I'll tell you whether we're early, on time, or need to get creative. I get to take the stress out of all of it so you can just vacation.
