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A group trip is not hard because of any one booking. It is hard because twenty people need the same answers, the money moves in every direction and the plan keeps changing. This checklist puts the decisions in the order that saves the most arguments.
Everything else hangs off the dates: flights, rooms, who can come. Offer two or three options with a deadline to answer, then pick the one that works for the people the trip is really for. Waiting for everyone to be free is how group trips never happen.
Most group trips go wrong over money nobody mentioned. Put a rough cost per person on the table before anyone books anything, including flights, rooms, the big nights and the boring things like transfers. People can say no to a number. They resent finding it out later.
A yes in the group chat is not a yes. Ask for a deposit or a booked flight by a set date, and plan around the people who have done it. It is kinder than holding rooms for people who were never coming.
Accommodation is usually the biggest single cost and the first thing to sell out. Book it once the numbers are firm, then settle who shares with whom before you arrive, not at the door.
One person usually pays for the rooms, a booking or a dinner and gets paid back later. Record each cost the moment it is paid: what it was, who paid, who it is split between. Settling up at the end is easy when the list exists, and miserable when it does not.
List what happens each day: times, addresses, what to wear, how people get there and back. Mark what is optional. Not everyone wants every night, and saying so up front stops people quietly dropping out.
The organiser becomes a help desk the moment the trip starts: what time is the boat, what is the address, what do I owe. Put the answers somewhere everyone can look them up on their phone, and keep that one place current when plans change.
Flights, passports and payments belong to each guest. Collect what you need for bookings, and share each person's details only with the people who need them.
Tell Anchor about the trip in one sentence. It lays out the days, takes the guests, and answers their questions so you do not have to. Free to start.