Planning a group trip
How do you plan a golf trip for sixteen to twenty people?
By Tom Wilson, Co-FounderUpdated July 18, 2026Planning a golf trip for sixteen to twenty people is a logistics job, not a group text. At that size the tee sheet, the lodging block, and the money all have to be locked in months ahead, and one person usually carries it. This guide walks the whole thing, from the first idea to the first tee, and where a hosted service actually earns its keep.
What actually changes when the group hits sixteen to twenty?
Everything gets less forgiving. A foursome improvises; twenty golfers cannot. Courses rarely hold four or five tee times back to back without booking far ahead, resorts want a room block and a deposit to match, and every choice now needs a yes from people in different time zones. The small problems a buddy trip shrugs off become the entire job.
- 16 to 20
- golfers to move
- 8 to 11
- rooms, a group block
- 4 to 5
- tee groups back to back
- ~6 mo
- lead time to lock it
the group size we run
rooming list, deposit, contract
booked months ahead
earlier for peak dates
A course only has so many morning tee times, and stacking four or five groups back to back on the days you want usually means booking months out, often with a deposit to hold them. Miss that window and your group is split across a morning and an afternoon, or across two courses, which is a different trip than the one everyone pictured. Lodging works the same way: ten or more rooms is a group block, with a rooming list due by a date, a deposit, and sometimes an attrition clause for rooms you reserved but did not fill.
Then there is the human layer. Twenty golfers have twenty opinions on dates, budget, who rooms with whom, and whether the non-golfers are coming. Every one of those is a small negotiation, and they all land on whoever volunteered to organize. That person is the real bottleneck, and burning them out is the most common way one of these trips quietly falls apart before it is booked.
How far out should you book, and in what order?
Start about six months ahead and work outward in the right order: dates and destination first, then the room block, then the tee times, then the roster and the money, and the fine details last. The order matters more than the exact dates, because each step depends on the one before it and the scarce things go first.
The trap is starting with the fun part. People want to argue about courses before anyone has agreed on a weekend, and by the time the dates settle, the rooms and tee times they wanted are gone. Lock the scarce, deposit-backed things first and let the details follow.
Six or more months out
Dates and destination
Get a firm weekend and a place before anything else. Everything downstream, the room block and the tee sheet, hangs on these two answers, and they are the hardest to change later once deposits are down.
Four to five months out
Room block and tee times
Reserve the lodging block and the consecutive tee times together, in writing, with the deposits they require. This is the step that actually protects the trip; everything after it is arranging people around a frame that already exists.
Two to three months out
Roster, rooming, and money
Confirm exactly who is in, pair up the rooms, add any companions, and start collecting money. Do this too late and you are guessing at head count while a deposit deadline runs down.
The final month
Transfers, pairings, and dinners
Ground transportation, the daily foursomes, and the group dinners. These feel urgent but they are the easy part, and they only work because the frame beneath them was set months ago.
Why does fronting everyone's deposits sink so many trips?
Because the organizer becomes the group's bank. To hold rooms and tee times you pay real deposits now, but you cannot collect from twenty people that fast, so one person floats thousands of dollars and then spends weeks chasing it back. That gap, between what is owed and what has actually landed, is where most group trips stall or die.
Here is the sequence that quietly ruins trips. The resort wants a deposit to hold the block. The course wants a deposit to hold the tee times. Both are due long before your friends have paid you a cent, so the organizer puts it on a personal card and hopes. Now they are out several thousand dollars and sending the same reminder text to the same three people every week.
It is not really about the money. It is about the friendship tax. Nobody wants to be the person nagging their buddies about a Venmo, and nobody wants to be nagged, so people go quiet, deadlines slip, and the organizer eats the awkwardness on top of the float. The trips that survive this are the ones that never put a single person in that position in the first place.
The fix is structural, not social: collect from each golfer directly, on a schedule, so no one is fronting anyone and no one is chasing anyone. We cover exactly how to do that in our guide to splitting group golf payments, because it is the single hardest part of a trip this size.
Who has to run it, and what does that person actually do?
Every trip has a captain, the one person who books, collects, and answers questions. On a buddy trip that is a friend doing a second unpaid job for two months: fielding texts, floating deposits, and making the calls nobody else will. It works right up until it does not, and it rarely survives more than a couple of trips before that person taps out.
Watch any group trip and you will find the captain. They picked the dates, called the resort, built the spreadsheet, and they are the reason it is happening at all. It is real work, done in the evenings, for people who mostly just show up. The healthiest buddy trips split the load, so someone owns the golf, someone owns the rooms, and someone owns the money, but that means three people are now coordinating with each other on top of coordinating the group. The captain role does not disappear; it gets a committee.
The honest question is not whether someone can do this. Plenty of people can and happily do. It is whether you want a friend spending their trip half-working, or whether that job belongs to someone whose actual job it is.
What does a done-for-you service actually change?
It moves the whole logistics job off your friends and onto someone who does it for a living. The tee sheet, the room block, the collecting, the transfers, and a person on the ground during the trip all become handled work instead of favors. What you keep is the fun part: your people, your foursomes, and a bill that everyone pays their own way.
This is what we built Arrive Golf to do, so here is the honest side by side. The point is not that doing it yourself is wrong. It is that every row below is real work that has to happen, and the only question is who does it.
| The job | Doing it yourself | With a hosted service |
|---|---|---|
| Tee times and rooms | You call, negotiate, and sign the block and tee-sheet contracts, then track the deposits and deadlines. | Held and contracted for you, with the consecutive tee times and the room block already arranged. |
| Collecting the moneyHow we do it | You front the deposits and chase twenty people over Venmo for weeks. | Each golfer gets their own secure payment link and pays their own way. No one fronts anyone. |
| If someone drops out | You eat their deposit or find a replacement yourself, fast. | A published cancellation ladder and free spot transfers, so one drop does not fall on the group. |
| During the tripHow we do it | You are on your phone fixing transfers and tee-time mix-ups instead of playing. | A concierge is on the ground handling transfers, tee times, and the day-to-day so you actually play. |
| The non-golfers | Left to figure out their own days, or left out. | A companion track of spa, excursions, and dining, timed around your tee sheet. |
For context on the shape of it, our current Westin Puntacana trip is five nights and four rounds across three courses, with ocean-view rooms, meals, private transfers, and a concierge on the ground, at around $5,600 a golfer. Whether you book with us or not, that is a useful yardstick for what a fully handled week actually involves.
When should you skip a service like ours?
Plenty of times, honestly. If you are eight regulars who have run the same trip five years running, or your group has a member who genuinely enjoys the spreadsheet, or the budget is tight enough that every dollar of service cost matters more than the time it saves, do it yourself. A hosted trip earns its keep on scale and hassle, not on every trip.
A service like ours is worth it when the coordination is the problem: a big group, people who do not all know each other, a destination nobody has booked before, or an organizer who is done being the bank. Take those away and the math changes. Here is when doing it yourself is the right call.
A small, seasoned group.
Eight regulars who have run the same trip five years running already have the muscle memory, and the overhead we remove is overhead you barely feel.
Someone who loves running it.
If one of you genuinely enjoys the spreadsheet, that person is an asset, not a liability, and handing it off would take away something they enjoy.
A bare-bones budget.
If the trip only happens because it is as cheap as possible, a fully hosted week is simply a different product than the one you are buying.
We would rather tell you that up front than sell you something you do not need. When the trip gets big enough, or the organizing gets old enough, we will be here.
Good questions
Common questions
- How many rooms do we need for sixteen to twenty golfers?
- Usually eight to eleven rooms, depending on how many golfers double up and how many companions come. At that count you are into group-block territory, which means a rooming list, a deposit, and a contract, so it is worth reserving the block well before you finalize exactly who is sharing with whom.
- How far ahead do we really have to book?
- For a group this size, aim for about six months out, and earlier for peak-season dates or a specific weekend. The binding constraint is not flights, it is consecutive tee times and a room block large enough to hold everyone, both of which get scarce and expensive the closer in you book.
- Does everyone pay separately, or does one person pay?
- On our trips everyone pays their own way. Each golfer gets their own secure payment link and settles a deposit and then a balance directly, so no organizer ever fronts the group's money or chases anyone. If you organize it yourself, setting up individual collection from the start is the single best thing you can do to protect the trip.
- What happens if someone drops out after we have booked?
- With us it follows a published schedule rather than falling on the group. A canceling golfer can hand their spot to a friend for free, or convert what they paid to cash or credit on our 120/90/45 ladder, and any credit we issue never expires. Organizing it yourself, a drop usually means the organizer eats a deposit or scrambles for a replacement.
- Can non-golfers come on a trip like this?
- Yes, and they should be planned for, not tacked on. On our hosted trips companions travel as equals on their own track of spa, excursions, and dining, timed around the tee sheet so everyone lands back together each evening. Even if you plan the trip yourself, deciding the non-golfer experience early keeps them from being an afterthought.
- What does a hosted golf trip actually cost?
- It depends on the destination, the courses, and the rooms, but as a real yardstick our current Westin Puntacana trip is around $5,600 a golfer for five nights and four rounds with ocean-view rooms, meals, transfers, and a concierge on the ground. The live per-golfer price is always shown on each trip page before you commit anything.
Written by
Tom Wilson, Co-Founder
Tom Wilson co-founded Arrive Golf and runs its trips himself, from the first tee time to the last airport transfer. He spent years organizing golf getaways for groups of sixteen to twenty before building the company to take that work off the organizer's plate.