Planning a group trip
How do you plan a golf trip for sixteen to twenty people?
By Tom Wilson, FounderUpdated September 2, 20267-minute guidePlanning 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.
- golfers to move
- 16 to 20
- the group size we run
- rooms, a group block
- 8 to 11
- rooming list, deposit, contract
- tee groups back to back
- 4 to 5
- booked months ahead
- lead time to lock it
- ~6 mo
- 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. Holding rooms and tee times costs real deposits now, but you cannot collect from twenty people that fast, so one person floats the gap and then spends weeks chasing it back. That gap is where most group trips stall or die.
Here is the sequence that ruins trips. The resort wants a deposit to hold the block. The course wants a deposit to hold the tee times. Both fall due long before your friends have paid you a cent. The working rule for a group this size: never commit a deposit you are not personally willing to lose, because until the money is collected that is exactly what you have done.
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, which our guide to splitting group golf payments covers in full.
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.
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. Splitting the load between a golf lead, a rooms lead, and a money lead helps, but the captain role does not disappear; it gets a committee to coordinate.
What does a hosted service actually change?
It moves three jobs off your friends and onto people who do them for a living: the contracting, the collecting, and the fixing that happens during the trip. Whether that trade is worth it is a real decision, so we gave it a guide of its own.
The short version: the tee sheet and the room block get contracted for you, every golfer pays their own way rather than paying an organizer, and somebody is on the ground during the trip. What you keep is your people, your foursomes, and a week nobody is half-working through.
The long version is a decision rather than a pitch, and it belongs somewhere it can be argued job by job, including the cases where planning it yourselves plainly wins. That is our guide to booking a hosted trip or planning it yourselves.
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, from $5,200 per golfer for double occupancy based on 16 golfers. 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. Eight regulars who have run the same trip five years running, a group with someone who enjoys the spreadsheet, or a budget where every dollar matters more than the time it saves should all keep doing it themselves.
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 we would rather tell you so up front than sell you something you do not need.
The full version of that argument is set out in the comparison guide linked above. 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: a rooming list, a deposit, and a contract. Reserve the block before you finalize 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. 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 the closer in you book.
- Does everyone pay separately, or does one person pay?
- On our trips everyone pays their own way, on their own secure payment link, so no organizer ever fronts the money or chases anyone. If you organize it yourself, setting up individual collection from day one is the single best thing you can do to protect the trip.
- Can non-golfers come on a trip like this?
- Yes, and they should be planned for rather than tacked on. On our hosted trips companions travel on their own track of spa, excursions, and dining, timed around the tee sheet. Deciding the non-golfer experience early is what keeps them from being an afterthought.
- What does a hosted golf trip actually cost?
- It depends on the destination, the courses, and the rooms. As a real yardstick, our current Westin Puntacana trip runs from $5,200 per golfer for five nights and four rounds, based on 16 golfers in double occupancy. The live per-golfer price is always shown on each trip page before you commit anything.
Written by
Tom Wilson, Founder
Tom Wilson 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.