Make It an Annual Thing: Turning a One-Off Group Trip Into a Yearly Tradition

It happens on almost every good group weekend, usually somewhere around the second bottle at dinner: someone says “we have to do this every year,” the whole table agrees, and then the group chat goes quiet for eleven months until someone finally asks whether it’s happening again. Big one-off occasions — a hen weekend, a milestone birthday, a big family reunion — are relatively easy to organise once, because there’s a fixed date forcing everyone’s hand. An annual trip has no such deadline, which is exactly why most of them never happen a second time. The groups that do make it a genuine tradition treat the follow-up as a separate piece of planning, not an afterthought of the first trip.

Why “we should do this every year” usually dies in the group chat

The first trip has a reason to exist — a wedding, a big birthday, a reunion after years apart. The second one doesn’t, and without an obvious occasion forcing a decision, nobody wants to be the one who chases everyone else for dates and money. Our sister brand Butlers in the Buff, which has organised group celebrations for more than 100,000 groups over 25 years, sees this pattern constantly: the enthusiasm at the end of a great weekend is real, but enthusiasm isn’t a booking. Something concrete has to happen in the days after the first trip, while everyone is still talking about it, or the idea quietly evaporates by spring.

Picking the trip that’s designed to repeat

Not every occasion makes a good annual trip. A hen weekend or a big fortieth is a one-off by definition — you don’t repeat someone’s wedding. But the underlying group — the university housemates, the school friends, the cousins who finally all got in one room — is exactly the kind of group that benefits from turning “we should do this again” into a standing October weekend or a January reset trip. The typical hen group is around 13 people (GoHen, 2025–26), which is also a very workable size for an annual group house trip — big enough that a large house makes sense per head, small enough that everyone still fits round one dinner table.

Money: the thing that quietly kills traditions

The first trip is often subsidised or unevenly funded — parents contributing to a hen weekend, or one person fronting the deposit. An annual trip needs a fair, repeatable way to split costs from year one, or it becomes the same person’s problem every single time until they stop offering. GoHen’s 2025–26 figures put a typical UK hen weekend at £250–£450 per person, which is a useful illustrative benchmark (illustrative) for what an annual group house weekend might cost per head once the house, food and one shared activity are split evenly. Agree the split — and who collects it — before the second trip is even confirmed, not after. Our group holiday budget planner covers fair ways to divide a shared house cost across a group.

Keeping the group open without losing what made it work

Some annual trips stay locked to the original guest list; others grow to include partners, then children, as the years pass. Decide this deliberately rather than by accident — a trip that quietly turns from “the girls” into a full family holiday can lose the thing that made the original group want to keep meeting. If the group does grow, our multi-generational family holiday guide covers how to keep a mixed-age group comfortable in one house without losing the original spirit of the trip.

Booking next year’s before this year’s weekend ends

The single most effective thing a repeat group can do is agree next year’s rough dates before this year’s group disperses — ideally on the Sunday morning, over the last pot of coffee, while everyone is still in the room and still enjoying the idea. It doesn’t need to be a booked house yet, just a locked weekend nobody double-books their own calendar against. One person taking on the actual booking — enquiring directly with an owner, since every enquiry on this site goes straight to the owner rather than through a call centre — keeps the momentum from the first weekend alive rather than letting it cool over winter. Trying something different each year also keeps a tradition fresh: a cocktail masterclass one year, a private chef dinner the next — Butlers in the Buff went from zero cocktail masterclass bookings before 2021 to around 120 a year now, which says something about how well that particular activity repeats for returning groups.

My honest tip

Don’t wait for someone else to chase the group. If your weekend just ended and everyone said “same time next year,” be the one who puts a rough date in the group chat before you’ve even left the car park — momentum dies fast, and the group that books early always turns out to be the group that actually goes again. Start browsing group houses for next year while this year is still fresh; you don’t need to commit, just to see what’s out there.