Planning a golf trip should feel like Christmas morning, not tax season. Yet every spring a fresh batch of well-meaning foursomes manages to bungle the basics: missed tee times, blown budgets, courses that eat high-handicappers for breakfast. Before you turn your dream getaway into a group-chat roast, learn from these five classic screw-ups and save yourself the therapy bills (and the Venmo chargebacks).
Mistake #1 – Syncing Flights After Booking Tee Times
Nothing like sprinting through Denver International in soft spikes because your first round is in three hours and two time zones away.
How to Avoid It
- Lock the travel window first (flights, layovers, baggage delays).
- Book tee times starting after check-in plus a stress buffer (think 4–5 hrs post-landing).
- I’ve talked about making life easier in my other post about Must Have Golf Items and I still think it’s worth noting here that if you make your travel easier with a CaddyDaddy travel bag, you can spare your back for the actual golf.
Mistake #2 – Walking 36 Holes a Day Because “We’re Here, Bro!”
Bandon Dunes, St. Andrews, Cabot Cliffs are all iconic, pure-walking layouts that’ll make your calves scream after the second loop. Marching two marathons with a bag is a recipe for Advil smoothies.
Damage Control
- Anchor the day with one signature 18-hole walk.
- Put the afternoon on “optional” status: par-3 course, range, or poolside Guinness.
- Appoint Theragun Mini as Official Trip Sponsor. Ten minutes on calves, hammies, and lower back = new legs by dinner.
- If you must go 36, rent a cart in the PM—or at least hire a caddie to carry the ego load.
Mistake #3 – Throwing High-Handicappers to the Wolves
Dropping your 28-handicap buddy at Bethpage Black is like inviting grandma to a death-metal festival. Hilarity turns to tears by the fourth tee.
Bad Example Hall of Shame
- Harbour Town – gorgeous, also 7,200 yds of tree-lined PTSD.
- Oakmont – slope 147; members brag about 3-putts.
- Pine Valley – if you get on and don’t break 110, you owe the member a kidney.
Friendlier Resorts for Mixed Skill Levels
- Pinehurst Resort (NC) – nine courses; No. 3 and The Cradle short course keep the double-digit caps smiling.
- Streamsong (FL) – three designs with multiple tees; no one feels punished.
- Coeur d’Alene (ID) – postcard-pretty, forgiving fairways, floating green everyone brags about. (See my CDA trip)
- Myrtle Beach grand-slam itinerary – 60+ courses from pushover to punishing, all cheap off-peak.
Mix formats (scramble, best-ball, etc.) so your 25-handicap pal isn’t weeping into his transfusion. Probably worth mentioning the USGA Pace-of-Play Guidelines. If you’re going to suck, suck fast. (Also doubles as solid life advice too)
Mistake #4 – Treating the Budget Like Monopoly Money
Sticker shock at the checkout desk kills vibes faster than a seven-putt.
How to Adult the Finances
- Group Spreadsheet (Google Sheets/Excel) – list every cost: flights, green fees, caddie tips, carts, range balls, booze, Uber XLs, souvenirs, “lost wedge fund,” etc.
- Slush Fund Hack (from our Coeur d’Alene trip)
- Everyone fronts a baseline fee covering shared items (lodging, group dinners, tee times).
- Chip in an extra $200-$300 “slush.” High-rollers can upgrade rooms, splurge on caddies, or grab bar tabs out of the same kitty without nickel-and-diming the broke buddy.
- Reconcile nightly with Splitwise or plain-old Venmo. Screenshot, share, done.
Mistake #5 – Booking Travel, Then “Winging It” on the Golf
You can’t have a golf trip without, you know, golf. Popular tracks aren’t holding secret tee times for procrastinators.
Lock It Down
- Set calendar alerts 9-12 months out for bucket-list resorts (Pebble, Bandon, St. Andrews ballot).
- Embrace shoulder season: lower rates, shorter queues, same bragging rights.
- No tee time? No trip. Full stop. Re-route to a destination you can book.
- Finish your confirmation email screenshot, then slam it into the group chat with the caption: “Booked—your move.”
Wrap-Up
Golf trips are too expensive to screw up on rookie mistakes. Line up your logistics, pace yourselves, respect the handicaps, do the math, and get ahead of the booking rush. Nail those five checkpoints and the only things you’ll slice are lime wedges for the post-round tequila.
Share this with your group chat before someone books a 6:00 AM tee time on travel day. Trust me, your liver (and your wallet) will thank you later.
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