When Your Group Genuinely Wants Different Trips
Beach people and city people. This is solvable, but not by compromise.
Maya Okonkwo
Editor, Out of Office
April 16, 2026 · 6 min read
The instinct is to find the middle: somewhere with a bit of beach and a bit of city, so nobody's disappointed. In practice, the middle option often means everyone is mildly disappointed instead, which is worse and harder to admit.
Better than compromise: sequencing
Two nights in the city, three by the water. Split-destination trips get a bad reputation because of transfer time, but if the two places are under two hours apart, it works, and both halves of the group get the trip they actually wanted.
- Lisbon then Comporta — 90 minutes
- Barcelona then Costa Brava — 90 minutes
- Naples then the Amalfi Coast — 90 minutes
- San Juan then Vieques — ferry or short flight
- Athens then Naxos — a ferry and a nap
Better than sequencing: optional days
One base, and one day where the group deliberately splits. Three people hike, three people don't leave the pool, everyone reconvenes for dinner with something to talk about. Groups treat this as a failure. It's the healthiest thing you can build into an itinerary.
Nobody remembers the day you all did the same thing. They remember the dinner where two people came back sunburnt with a story.
When it really can't be solved
If half the group wants a £600 weekend and half wants a £2,400 week, that isn't a destination problem, it's two different trips. Do the cheaper one this year with everyone, and let the expensive one be a separate, smaller trip nobody has to feel guilty about.
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