These are the rules I use when a family of eight to twenty asks me to build a celebration trip, drawn from reunions, milestone birthdays and multi-generation weeks that ran without a single argument about logistics.
The tips list
Set the budget before the dates
Publish a per-person range, flights excluded, and ask everyone to confirm within two weeks. Money conversations held early prevent half the group from quietly opting out later.
Pick one house, not three hotels
A single villa with a kitchen and a shared living room solves meals, evenings and the cousins who want to stay up late. Book bedrooms for couples and a separate wing for the grandparents.
Take deposits, not promises
A deposit converts a maybe into a booking and lets you hold the property. I set the deadline at sixty days out so a late drop can still be replaced.
Write the one document everyone reads
Dates, address, transfers, what is included, what each person owes and who to message. One page, no attachments, updated in place rather than rewritten.
Keep a free morning every day
Three planned activities in a row breaks a group. One open window each morning lets people sleep, swim or do nothing, and the afternoon session runs better for it.
Assign one person per task
Groceries, transfers, restaurant bookings, a photographer. Shared ownership beats a single exhausted organiser, and it gives everyone a stake in the week working.
Eat one meal out, not three
Breakfast and dinner at the house keep costs and allergies manageable. Reserve a single long lunch somewhere memorable instead of chasing a table every evening.
Book transfers as a block
One coach for arrival beats five cars and a group chat about parking. Schedule the return transfer with a buffer for the two flights that leave earliest.
Plan for the widest age range
Two activities a day should work for a six-year-old and a seventy-six-year-old: a boat trip with shade, a market with seating, a beach with a gentle entry.
Carry a contingency fund
Ten percent of the budget covers a weather switch, a taxi run or a birthday cake that nobody budgeted. Agree on who authorises spending from it before you go.
Handle payments cleanly
Collect in one currency, keep a running balance in the shared document, and settle the final split the week you return while the numbers are still fresh.
Agree a dress code, or agree there is none
One line in the document stops the group arriving at a long lunch in three different outfits. Most celebration weeks run better with a single smart evening and everything else relaxed.
Give the quieter members a job
The relative who never volunteers still wants a role. Ask them to carry the playlist, choose the coffee stop or hold the camera for an hour, and the trip stops feeling like someone else's plan.
Protect the airport departure
Book one coach for the return leg timed to the earliest flight, with a second pickup for the late departure. Splitting cars on the last morning is how groups lose people at the terminal.
End with something everyone can attend
A last-night dinner with a short toast closes the trip properly. Schedule it early enough that nobody is packing while it happens, and the week finishes on a shared moment rather than a checkout.
If two tips carry the whole trip, they are the first and the fifth: agree the money, then protect the empty mornings. Everything else in the list is detail that a shared document can hold for you, and a group that has those two sorted will forgive the rest of the imperfections on its own.