destinations · 1 November 2026 · By Simon Berriman, Founder of Caddie Live

How to Plan and Score a Golf Trip in 2027

How to Plan and Score a Golf Trip in 2027

Every golf trip has an organiser, and the organiser is the one person who does not fully enjoy it.

They chased the deposits. They know who has not paid. They worked out the pairings at eleven o'clock the night before on the back of a drinks menu, and on the last afternoon somebody asks who actually won the week and nobody can answer, because the scores are spread across three phones, a WhatsApp thread and a damp scorecard in a hire car.

The trip is still good. It is just better when that person gets to play golf too.

This is how to set a 2027 trip up so the admin is done before you fly and the week has a winner at the end of it.

Book it now, properly

Autumn is when 2027 trips get booked, and the reason is simple: the good weeks at the good resorts go first, and the gap between booking in November and booking in February is usually a few hundred pounds a head.

Three things to settle before you book anything.

The group. Get a firm number before you price it. Trips that are sold as "about twelve of us" end up as nine, and nine people paying for a twelve-person villa is the row that starts the week badly. Ask for a deposit to confirm. Someone who will not put down £100 in November is someone who is not coming in May.

The ability spread. A group with a four and a twenty-eight in it can have a great week, but only if you pick courses they can both get round. A championship links in a crosswind is a wonderful idea until half the field is reloading off the first and the round takes five and a half hours.

The budget, honestly. Agree a per-head ceiling before anyone falls in love with a resort. Then build to it: flights or drive, accommodation, green fees, buggies, car hire, food, and a float for the things you have not thought of. Put the float in. There are always things you have not thought of.

If you are still choosing where to go, our guide to the best golf trip destinations in Europe for groups runs through the options by group size and budget.

Handle the money once

Collect everything up front, in one go, from everyone. Not deposits from some and balances from others and a vague promise from the one who is always slow.

The organiser who is personally out of pocket for four thousand pounds in March is the organiser who spends the trip doing mental arithmetic. Set two dates, a deposit in November and a balance eight weeks out, and hold both. One person missing a deadline is a conversation. Four is a crisis.

Keep a running sheet that everyone can see. Who has paid, what is left, what the per-head total actually came to. Trips go wrong on money far more often than they go wrong on golf, and almost all of it is avoidable by writing the numbers down where people can check them rather than having to ask.

Pick a format for each day, not one for the week

The best trips vary the format. A week of medal stroke play is a long week for anyone outside the top three, and the people who are out of it by Tuesday stop caring by Wednesday.

A shape that works for four days:

Day one, a scramble. Everyone plays, nobody is exposed, the four-hour round is relaxed and the group settles. The right opener after a travel day.

Day two, fourball better ball. Pairs, so there is a partner to carry you and someone to blame. Keeps the higher handicaps fully involved.

Day three, singles Stableford. The individual test, on the best course of the trip. This is the one people remember.

Day four, team matchplay. Ryder Cup format, captains, the whole thing. Ends the week on something that feels like an occasion rather than another round.

Score an order of merit across all four so there is an overall winner, and run the daily competitions on top. A player can have a shocker on day two and still win the week, which is exactly what keeps everyone interested through to the last tee shot.

Add the side games. Nearest the pin, longest drive, skins, most birdies. They cost nothing, they give the day texture, and they give the person who shot 94 something to have won.

Make the scoring work on tour

This is the part that falls apart, and it falls apart for predictable reasons. There is no clubhouse TV to plug into. Signal is patchy on half the courses. Not everyone is going to download an app, particularly the two who joined late.

What actually works: everyone scores on their own phone as they play, the leaderboard updates for the whole group, and anyone who wants to look just opens a link.

Caddie Live was built for this. Different format each day with one running overall leaderboard across the whole trip, so the day's result and the trip standings are both live. Teams, flights or divisions if the group needs splitting. Skins, nearest the pin and the daily and trip winners tracked automatically, along with the stats worth arguing about, like who made the most birdies. If signal drops, players keep scoring and it syncs when the connection comes back. Guests join by link with no download, which matters more than it sounds when there are twelve of you and two are on borrowed phones.

Set the trip up once, share one link, and the leaderboard follows the group from the first tee to the final pint. Free while we are in beta.

[Plan your trip free in Caddie Live →]

The week before

• Confirm final numbers with every course and send the rooming list
• Send the itinerary: tee times, addresses, who is in which car, what the dress code is at each club
• Do the pairings for day one and publish them. Doing them on the first tee costs twenty minutes and some goodwill
• Set the trip up for scoring and get everyone on the link before you travel, not in the car park
• Check the buggy bookings. Buggies are the single most common thing to be wrong on arrival
• Agree what the handicap allowance is for each format and tell people before they play, not after

Then play

The point of all of this is that the organiser gets to put their phone away on the first tee and play golf like everybody else.

The money is in, the tee times are confirmed, the formats are agreed and the leaderboard is running itself. Nobody has to ask who won, because the answer is on everyone's phone.

[Plan your trip free in Caddie Live →]