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Learn - 8 min
Trips - the annual buddies trip in one app
Plan a 4-day trip for 8-16 friends without a Google Sheet. Follow the steps below on caddie.fun.
Tee sheets, foursome rotations, expense splits, and a recap your group will read for years.
Pinehurst Trip
Day 2
- No. 274
- No. 478
- No. 881
For captains
You are the trip captain. This is the canonical setup flow, plus the gotchas that bite captains every year.
- 1
Pick a trip template
Three templates: 3-day weekend, 4-day, and custom. Templates pre-fill the day count, expected foursome rotation cadence, and the standard markets surface. You're not bound to a destination.
- Captain picks own courses; no destination binding
- Switch templates any time before the trip starts
- 2
Use the AI Trip Planner
Paste your intent (dates, headcount, courses, vibe) and the planner returns a full draft: tee sheet, foursome rotation, expense lines, and day labels. You see the confidence score, the rationale, and any warnings before you accept.
- Confidence + rationale + warnings shown before you accept
- Reroll any section without losing the rest
- 3
Set up Calcutta
Calcutta is optional. If on, the trip surfaces a sealed-bid auction on participants - top 3 finishers' winning bidders share 70/20/10. Bidders see only their own bids.
Heads up: Calcutta is one bid per target. Bidders see only their own. Communicate the close time to the group.
- 4
Lodging, companions, and transport
Assign lodging per night and add transport blocks where they matter (airport pickups, course shuttles). Add non-golfer companions (a spouse, a friend along for the ride) - they share lodging and the expense splits but never appear on the leaderboard. All of it shows up on every player's itinerary card.
- Per-night lodging assignments with roommate handles
- Companions split expenses + lodging without being scored
- Transport block ships when shuttle integration is ready
- 5
Photos and the trip recap
Players upload photos to the trip's Memories all weekend - they live alongside the auto-generated highlights. Four hours after the trip ends, an AI-generated 3-act narrative auto-creates and pushes to the group, with Markets entries woven in so the calcutta winner gets their roast moment.
- Anyone on the trip can add photo memories
- Recap auto-generates; captain can edit before sharing
- Shareable card link drops cleanly into group chat
For players
You got the invite. Here is what you actually have to do.
- 1
Accept the invite
Tap the deep link from the captain's text or chat. Your itinerary, lodging, foursome rotation, and any open markets show up immediately on your trip card.
- 2
Pick on the trip
Trips light up Markets at three levels: trip-level (who wins the week), day-level (who's low on day 2), and the Calcutta auction. Pick early; locks are firm.
- 3
Settle expenses
Shared dinners, caddie tips, and ride splits route through Venmo deeplinks the captain sets up. One tap per line item, no spreadsheet math.
- 4
Read the recap
Four hours after the trip ends, the AI recap pushes. Open it, share the card link to the group chat, and start campaigning for next year's roster.
FAQ
Common questions
How big can a trip be?
Tested up to 16 players across 4 days. Larger groups work but the planner output gets denser; expect to do more manual tuning.
What if my friend can't make it?
Captain can swap players in the foursome rotation. The tee sheet auto-rebuilds and players get push notifications about their new pairings.
Do trips support entry fees?
Yes, optional. Entry fee goes into a prize pool with format-specific payout rules. Caps still apply on per-round side games.