Sick Golf Trips
Kerry Hew & Berkley Hoagland
Real golfers. Real budgets. Really sick trips. The stories, formats, budgets, and traditions behind unforgettable golf trips for everyday golfers. We dissect the trip your buddy group is actually capable of pulling off — and the small choices that turn it from "fine" into a story you'll tell for the rest of your life.
Episodes
I Lost $4,000 to Wayne Gretzky's Wife on a Golf Course
Keith Zubchevich has played golf with more Hall of Famers than most people have watched on TV. From a standing tee time with Marcus Allen, Alonzo Mourning, Richard Dent, and Ronnie Lott to 36 holes with Lawrence Taylor on his birthday, Keith's golf life reads like a sports documentary. But the story that cost him the most money involves Wayne Gretzky, Janet Gretzky, and a $4,000 golf bet at Sherwood Country Club.We cover:How Keith bluffed his way into Tiger Woods' locker room at Castle PinesWalking three holes inside the ropes with Tiger and Fluff before security caught onPlaying 36 holes with Lawrence Taylor — chain-smoking cigars and cigarettes, shooting 71-69 from the tipsThe $4,000 Sherwood bet with Janet Gretzky that Michael Jordan refuses to takeWhy Paso Tiempo is "possessed by demons" and almost broke Keith's spiritA Pebble Beach weekend with Spyglass and the Lodge — worth every dollar50 pairs of Jordan golf shoes and the philosophy of looking like you can playBeat the Pro charity stories: hitting it to 6 inches and beating hackers left-handedThe two rules of golf: play with people you like, and lower your expectations
Your Body Is the Problem, Not Your Swing
Shaun Diachkoff is a TPI-certified golf fitness coach who works remotely with everyone from weekend warriors to tour players. He lives in the Cayman Islands, grew up in Australia, and spends half his year traveling to meet clients at courses like Ridgewood and Aronomink — places that won't let you take a cart. Shaun explains why most golfers are trying to tune a Ferrari engine on a rusted chassis, how he screens clients like a first date, and what Barnbougle Dunes in Tasmania actually plays like when the wind is blowing 40 knots.We cover:Why walking 18 holes exposes your real fitness levelTPI certification and what Titleist Performance Institute actually teachesThe "busted chassis" analogy — why fitness has to come before swing mechanicsHow Shaun built Fairway Performance from a CrossFit gym in Sydney to a remote coaching businessClient screening: how he smells the "crazy ex" in the first 15 minutesWhat it's like playing the only 18-hole course in the Cayman Islands (spoiler: bring 70 balls)Barnbougle Dunes and the Lost Farm — Tasmania's answer to links golfMatch play mentality and Australian pennant competitionsWhy a 67-year-old with six surgeries gained 50 yards in eight months
An Indoor Golf Country Club? We Tried It
We visited TeeBox in San Marcos, CA and spent an hour with Raymond Mistarz, a certified TPI coach, inside one of the most tech-forward indoor golf facilities in the country. Trackman simulators, 3D motion capture, physical assessments, and AI-driven swing analysis — all under one membership.Visit https://tbx.golf/san-marcosThis week we cover:Why TeeBox starts every golfer with a physical assessment before they ever hit a ballHow the TPI screen reveals swing flaws that no simulator can fix on its ownWhat Trackman and 3D motion capture actually show you (and why it matters)Membership pricing, founder's rates, and what you actually get for your moneyThe SportsBox AI app and Forge Fit club fitting included in the membershipGames, mini-competitions, and why it's as much a hangout as a training facilityUsing the simulator to preview your next golf trip before you ever leave townTeeBox expansion plans: 30+ locations and growing
The St. Andrews Hack Nobody Tells You About
Dr. Chase Cunningham breaks down how he got on St. Andrews by buying a caddy drinks at the Nine Iron bar, why Shadow Creek might crush St. Andrews in quality (but not in history), and how he's turning an indoor golf simulator into a bank-funded man cave.We cover:The Nine Iron bar hack: how one night of drinks landed a St. Andrews tee timePlaying Scotland: Carnoustie, Turnberry, King's Course, and the Old CourseThat 77-degree Scottish day with 1,500 people watching the first teeWhy he piped his drive at St. Andrews and walked 100 yards before the rest of his group hitTaiwan golf: caddies who only speak Chinese and courses that force you to rideStableford scoring: why it's better than stroke play for group tripsWalking vs riding: the study that says walkers shoot 7-9 strokes betterIndoor golf done right: OTG (On The Green) in Northern VirginiaShadow Creek vs Pebble Beach vs St. Andrews: the $1,200 vs $400 debateBucket list: Thailand, Bandon Dunes, Ireland, and more
Piggybacking a Tournament Into a Golf Trip
Lance Botthof joins us to break down how he turned Ram's Hill's amateur "Ramateur" tournament into a full-blown group trip — growing it from 4 guys to 12, with welcome parties, meals, and handicap flights all built in.We cover:• How the Ram's Hill "Ramateur" tournament works (2 rounds, 3 flights, gross + net)• Lance's group growing from 4 to 12 people — and aiming for 16 next year• Welcome party Friday, rounds Saturday & Sunday, all meals included• Why Borrego Springs Inn is the move when the on-property houses fill up• Handicap flights and the "over 60 plays white tees" rule• The Sunday league at The Crossings — $40 buy-in, skins, and no drama• Side bets, gambling, and why everybody has action with somebody• Future trip to Sand Valley (and maybe The Lido) next June• How Lance fills 12 spots in 2-3 days with a single text• Rating Ram's Hill against other courses he's played
The Spain and Portugal Golf Trip Nobody Talks About - Joseph Bronson
Award-winning golf author Joseph Bronson breaks down why Spain and Portugal are the underrated golf destinations most American golfers completely overlook — and why they might be the smartest international trip you can take.This week we're joined by Joseph Bronson (@josephbronson), award-winning author of the PARdon Me book series, former Silicon Valley tech executive, and 40-year veteran of the world's best golf courses. At 78 years old he's still playing twice a week, walking courses in Ireland, and planning his next trip back to Spain.We cover:Why Spain and Portugal deliver a "very good US experience" with better weather12 days across the Algarve and Costa del Sol — 7 days in Spain, 5 in PortugalCourse recommendations: Dumas, the Els Course, Sano Grande, and ValderramaGreen fees: expect $350-$500 per round at the top tracksCaddies in Spain and Portugal — great experience, no cart restrictionsThe Stillwater Golfing Society at Pebble Beach and how a group of 16 travels togetherA hilarious Royal Dornoch story from ScotlandWhy he rates Spain/Portugal equal to Scotland/Ireland — just a completely different experienceHis "20th Hole" blog and book series where all proceeds go to university golf programsCourse design philosophy: why he hates "tricked up" holes and loves playabilityThe Friars Head mental game story: shooting 45 on the front, 37 on the back in 37 degrees
How They Turned a Friend's Wedding into a Golf Trip
This week we're joined by Harrison Carter, a VP of strategic marketing from Boca Raton, FL who picked up golf three years ago and hasn't looked back. He went from shooting 120 to an 11 handicap, and now he's loading up on golf trips. This one started as a wedding invitation and turned into back-to-back rounds at one of the most scenic courses in the country.We cover:• How a wedding invitation became a golf trip• Edgewood Tahoe — $500 rounds and views that justify the price tag• Elevation golf: when your driver gains 40 yards overnight• The best-score-per-hole format that works with mixed handicaps• Balancing wedding duties with tee times (the groom survived)• Lake Tahoe logistics: where to stay, when to go, and what to expect• Harrison's upcoming trip slate: Alabama RTJ, PGA Frisco, and Stream Song - Bone Valley
How We Got Sold on Michigan for our Golf Trip
This week we're joined by Jerry McGarvey, Kerry's friend and volunteer organizer behind a guys' trip to Northern Michigan that over-delivered on every front. Jerry walks us through the courses, the expectations, the optional logistics, and why this will be a sick golf trip.We cover:• How the "Michigan? Really?" skepticism turned into "when are we going back?"• Forest Dunes — a Tom Doak public gem that belongs on every golfer's list• Bay Harbor — Pete Dye cliffside golf along Lake Michigan• Arcadia Bluffs — views and vibes that rival any coastal destination• Why Michigan's quality-to-cost ratio punches above its weight• Group size, logistics, and how to pull off a seamless multi-course trip
A Couples Golf Trip to Cabot Cliffs: The #1 Golf Course in Canada
A Couples Golf Trip to Cabot Cliffs: The #1 Golf Course in Canada Michael Son joins us to break down his couples golf trip to Cabot Cliffs in Nova Scotia — three couples, three courses. Michael breaks down the trip, lessons learned, and what he would change if/when he goes back.We cover:• Cabot Cliffs (#4 in the world, #1 in Canada) — why it lives up to the hype• Cabot Links — scoring better when the wind cooperates• Fox Harbor — the sleeper destination with golf, wine, and axe throwing• The couples trip dynamic: guys vs guys, girls vs girls• Using Global Golf to handle tee times, lodging, and logistics• The Canadian dollar advantage• Why walking-only courses demand a different level of preparation• How to structure a Nova Scotia golf trip: Halifax → Cabot → Fox Harbor
Myrtle Beach: The Golf Capital of the World
Mirko Zizka joins us to break down his annual 8-guys golf trip to Myrtle Beach — 80-100 courses, budget-friendly pricing, and why this destination has been in his group's rotation for over 15 years.We cover:• How an 8-guy group plans a 7-night, 7-round trip without losing their minds• Using a local agency to book tee times and accommodations• The two-man scramble format that keeps everybody engaged• Playing the "World Tour" course with replica famous holes• Why October off-season delivers the best value• Budget breakdown: ~$150/round, cheap accommodations, total trip cost• Rotating destinations: Myrtle Beach, Scottsdale, Mexico, Dominican Republic• 80-100 courses in the area — why repetition isn't a problem
The Best Golf Trip Isn't Just Playing Golf
Sick Golf Trips Podcast Ep 15: Maybe the Ultimate Golf Trip is Playing and Watching! — Kyle Porter, Normal SportKyle Porter of Normal Sport joins us to break down his golf trips covering major tour events, including the Open Championship trip to St. Andrews and makes the case that the ultimate golf vacation might be one built around a major tournament — where watch the best players in the world play historic courses by day and play yourself by night.
Sand Valley: Bandon Dunes Sister Resort | Sick Golf Trips Podcast Ep. 14
Pete flew from Long Island to Madison, Wisconsin, waited over a year on the waitlist, and finally got his college crew onto one of the most talked-about golf destinations in the country — Sand Valley. Spoiler: it lived up to the hype.This week we're joined by Pete, a software sales pro and golf app founder from Long Island, New York. Pete and 7 of his college buddies have been doing an annual golf trip for 5+ years — and Sand Valley was their white whale. He breaks down the entire trip: the 36-hole days, the caddy experience, the 8-man cabin, the $1 taco shack, and how the draft format keeps the competition alive all weekend long.We cover:Getting on the waitlist — expect at least a year out (maybe two)Flying into Madison and vanning up to the middle of nowhereSand Valley, Mammoth Dunes, Sedge Valley, and The Lido — all four coursesWhy you absolutely need caddies and how to get the same looper for multiple roundsThe snake draft format that keeps 8 guys locked in all weekendMatch play rules: team play vs. Sunday singlesWhy the 8-man cabin beats hotels every single timeFull cost breakdown: ~$300/round + $120-150 caddy tipsThe legendary $1 taco shack right on propertyHow Sand Valley stacks up vs. Pinehurst, Streamsong, and Bandon DunesPete's new golf app — Golfed — to track every course you've ever played
The Perfect Ireland Golf Trip: Do It Before You Can't | Sick Golf Trips Podcast Ep. 13
This week we’re joined by Greg Johnson, a Chicago golfer who met Berkeley on a local course and casually mentioned he’d just returned from a 7-day Ireland trip with 12 guys. One thing led to another, and here we are. Greg breaks down the entire journey: how they planned it through Fairways & Fun Days, why they picked Ireland over Scotland, and what it’s like walking some of the most iconic links in the world with your oldest friends.
He Played 580 Courses in 1-Year! | Sick Golf Trips Podcast Ep. 12
This week we’re joined by Patrick Koenig — a former software salesman turned golf course photographer who set the world record by playing 580 different 18-hole golf courses in a single calendar year. Patrick tells us how he went from a comfortable corporate gig to living in an RV, driving across 41 states, and turning his passion for golf photography into a full-time career.
The Ultimate Guide to a Wisconsin Golf Trip | Sick Golf Trips Ep. 11
Jason Kauflin of Wisconsin Golf Trips joins us to break down everything you need to know about planning a Wisconsin golf trip — the courses, the costs, the logistics, and why Wisconsin quietly has the best public golf in America. We cover:• How Jason went from stay-at-home dad to running golf trips for 84-person groups• The Kohler "requirement" and how to navigate their package maze• Whistling Straits, Erin Hills, Sand Valley, Blackwolf Run — what to play and when• Group sizes: 4, 12, 44 — what's actually manageable• Walking courses, caddies, and why Erin Hills will test your knees• Hickory golf — yes, Jason plays 105-year-old clubs full time• Scotland vs Ireland from a guy who books both• Booking timelines: when to plan and how far out Find Jason at www.wisconsingolftrips.com and https://x.com/WIGolfTrips
Golf, Guinness, and Good Craic in Ireland | Sick Golf Trips Ep. 10
This week we're joined by Joe (@golftravelerjoe), a Pinehurst member who has played 483 golf courses and counting. Joe breaks down his epic 8-day Ireland golf trip where he brought 20 Twitter followers together to play 7 rounds across the West and East coasts of Ireland. We cover everything: the courses, logistics, caddies, costs, group dynamics, weather, pub culture, and why you should never try to self-drive your first Ireland golf trip.
Put Pinehurst on the Golf Trip Bucket List | Sick Golf Trips Ep. 9
In Episode 9, we welcome Tony Rudy to the Sick Golf Trips podcast to break down his annual Pinehurst golf trip — 15 guys, caddies, gambling, and some of the most diabolical greens in golf.They dive deep into what makes Pinehurst No. 2 special, why No. 4's greens might actually be harder, the legendary caddy stories, and the wild drainage that gets greens tournament-ready 10 minutes after a storm.You'll also get the full cost breakdown, the ideal 5-day/4-night itinerary, best team formats, where to eat (Beehawk, the new distillery from a Black Hawk Down veteran), and how to book tee times without needing a member hookup.
Is There a Better Mens Locker Room Than Kiawah Island Club? | Sick Golf Trips Ep. 8
In Episode 8, we welcome Ryan Berger to talk about his annual college crew golf trip. In 2024, they went to Kiawah Island in South Carolina. This group of guys met in their freshman year of college in 1998 and their 2024 trip to Kiawah was one for the books. Ryan breaks down how an unofficial "golf trip committee" plans everything from courses to Airbnbs, why they timed it around NFL Draft weekend, and the unforgettable experience of having dinner inside a private country club's men's locker room (yes, really). They played Cougar Point and two private courses at Kiawah Island Country Club, had a private chef cook at their rental house, and split into "fat guys vs skinny guys" for a hilarious team competition. We also dig into the caddy experience at Kiawah, the travel logistics of flying into Charlotte and driving down, crew dynamics across married/single/divorced guys, and Ryan's incredible hole-in-one witness story from Monarch Beach.
Would You Brave the Desert Heat at PGA West in Palm Springs? | Sick Golf Trips Ep. 7
In Episode 7, we welcome Tam Nguyen to talk about his legendary 19-year-running golf tournament at TPC Stadium Course at La Quinta Resort in Palm Springs. What started as a post-college guys' getaway morphed into a full-fledged annual competition with stroke play, a Ryder Cup-style team event, a 3-foot trophy, and the infamous "Nibe Award."
Bucket List Golf Trip at Pebble Beach | Sick Golf Trips Ep. 6
Mike Preston wanted a special way to ring in his 40th birthday. He arranged a tight foursome with his brothers, they brought the wives for the after-golf festivities and did it right. Mike shares stories, tips and costs that made their experience a Sick Golf Trip.
18-Hole Golf Course All To Yourselves at Honey Pond Farm | Sick Golf Trips Ep. 5
Kerry and Berkeley welcome guests Danny Roberts and James Ramos to break down Kerry's first-ever organized golf trip to Honey Pond Farms in Middletown Springs, VT. They cover booking a private 18-hole course for 16 guys, the unique scramble format with shared fairways and greens, travel headaches in rural Vermont, total costs, house amenities, and more. This is definitely a unique experience, but who is it best for?
Country Club Hook-ups at Wingfoot & Sebonack | Sick Golf Trips Ep. 4
Chris Roach, CEO of Porter Road, joins the pod to share his experiences touring a few courses located on the Great Peconic Bay on Long Island. It's an intimate trip with a very good friend, but they made it a family trip around golf. Unfortunately, his golf game ruined one of his golf experiences, but that's golf!Definitely try the meat at https://www.porterroad.comIt really is top of the top meat. You won't regret it!
A Hidden Gem in Northwest Michigan | Sick Golf Trips Ep. 3
Dr. Chris Kurrami joins the pod to break down his annual golf trip to Bay Harbor, Michigan, a hidden gem on the shores of Lake Michigan, north of Traverse City. The good doctor shares how he first got invited, the Stableford scoring format they use, and their legendary player auction where you can bet on the winner of the tournament. We also cover surrounding courses, travel logistics, costs, and why this trip is an annual lock for their crew of 16-24 guys.
PGA Tour experience in Innisbrook | Sick Golf Trips Ep. 2
Jeff Kaplan joins us to break down his annual guys golf trip. This year, they went to Innisbrook Resort in Palm Harbor, Florida — home of the Copperhead Course, where the PGA Tour's Valspar Championship is played. Jeff has been organizing this group's golf trips for 18 years, and they've got it dialed in with a championship belt called "Live Until You Die," a unique point scoring system, live scoring, and rotating team formats.We get into the full playbook — how they vet new members, why they prefer to change venue every year, the real cost breakdown ($3K all-in with unlimited golf), and the emotional story of how a friend recovering from a stroke inspired the belt tradition. Plus: how it feels to play a PGA course in full tournament conditions two weeks before the pros arrive.
Is Bandon Dunes the Disneyland of Golf? | Sick Golf Trips Ep. 1
Bandon Dunes. No carts. No excuses. Four guys take on golf's bucket list destination and find out if it actually lives up to the hype. Our guest breaks down his trip 4-guy trip: the courses, the logistics, the cost, and weather, and more. Is this trip an Annual Lock or a Once-in-a-Lifetime, one-and-done? If you've ever had this trip in your group chat, this episode is for you.