How to Plan a Reunion Trip with Old Friends

Pick a destination everyone can actually reach within 2-3 months, set a firm budget everyone agrees to upfront, and use a shared document (Google Sheets works) to track decisions and costs in real time. Pick one person to be the organizer, not a committee.

Get honest about logistics first. Before you fall in love with a destination, ask everyone: What's your max airfare budget? When can you take time off? Do you have a passport? What's your max total spend? Write down the answers. A destination that's perfect for two people and impossible for three is not a destination—it's a problem waiting to happen.
Choose a destination that works for everyone's constraints. Look for places that are roughly equidistant from where people live, or at least where flight costs are similar. A trip to Mexico might cost someone from Arizona $150 and someone from New York $400. That matters. Pick somewhere everyone can get to for under $300-400 in airfare unless everyone explicitly agrees otherwise.
Pick your dates and lock them down. Give people a 2-3 month window before the trip to commit. Set a deadline: 'We're booking flights March 1st. Tell me yes or no by February 15th.' People will respect a deadline. They will not respect 'let me think about it indefinitely.'
Set a total budget per person and break it down. Don't just say 'budget-friendly.' Say: 'Total budget is $1,200 per person. That's flights ($350), accommodation ($400), food ($300), activities ($150).' When people see the breakdown, they know what they're signing up for and can decide if it works.
Pick accommodation as a group, not a committee. One person researches 3 options that fit the budget and sends them to the group with pros/cons listed. You vote. You pick. You book within 2 days. Don't spend 3 weeks debating 47 Airbnbs. Pick the one that sleeps everyone, is within budget, and has decent reviews.
Create a shared budget tracker from day one. Use Google Sheets. List all shared expenses (accommodation, group meals, transportation, activities) and who paid what. If one person books the house and flights and another buys groceries, you need to track it. Settle up before you leave or everyone will resent each other.
Build a loose itinerary, not a military schedule. Day 1: Arrive, settle in, casual dinner. Day 2: This one hike people want, plus free time. Day 3: Free day, optional group meal at night. You don't need to schedule every hour. People came to hang out, not to follow a clipboard. But have 1-2 things everyone agreed on in advance, so nobody shows up expecting all beach and finds out you're doing museum tours.
Communicate expectations about drinking, partying, pace. This matters. Are you a 'stay up until 2am every night' trip or 'go to bed at 10pm' trip? Are you drinking? Is someone not? Talk about it casually before you go. One person's idea of a party trip and another's idea of a peaceful getaway will ruin things fast.
Designate one person as the coordinator. Not a tyrant. One person who makes final calls when there's a tie, keeps the shared doc updated, sends reminders about payment deadlines, and coordinates group logistics. This should be someone organized and not easily annoyed. Everyone else respects their role.
Settle all money before or immediately after the trip. Use Splitwise or just a simple spreadsheet. If the trip cost $5,000 total and there are 5 people, each person owes $1,000. Subtract what they already paid. Settle the balance before everyone goes home. Don't let it linger. Money resentment will kill the friendship faster than any bad hotel.

What if someone can't afford the trip we chose?: You picked the wrong destination. Go back and pick a cheaper one, or one closer to them. The point of a reunion is everyone being there. A trip where one person is missing or stressed about money the whole time isn't a reunion.
How do we decide what to do each day if people want different things?: You don't need to do everything together. Pick 1-2 must-do activities everyone agreed on before the trip. The rest of the time, people can split up. Some people hike, some people sleep in. You reunite for dinner. Everyone's happy.
Someone's being flaky about committing. Should we wait?: No. Set a deadline, tell them what it is, then book without them. People need deadlines or they'll be noncommittal forever. If they commit late, they can book their own flight and join. But don't let one person's indecision hold up five people.
What if we go over budget?: It happens. Track everything and split costs fairly. If the house cost more than expected, everyone pays a little more. Be transparent about it immediately, not at the end. Surprises about money ruin trips.
How do we handle someone's partner or new person joining?: Decide this before you book. Are partners coming or is this friends-only? If they're coming, they're in on the budget conversation from the start. Don't spring extra people on everyone.
What if we fight or things feel awkward?: That's normal. You haven't all been together in years. You're tired and hungry and sharing a small space. Have one good meal, get some sleep, wake up and try again. It usually passes by Day 2.