Land at Charleston International, grab a rental car, and about 40 minutes later you roll up to the gates of Kiawah Island. That drive matters, and I’ll come back to it, because how you get around Kiawah is one of the few things people get wrong on their first trip.

I’m Pete, and I run Golfed, an app for logging every course you’ve played, so a place like Kiawah is right in my wheelhouse. You can knock out five legit championship courses in one trip, all run by the same resort, all a short drive apart. It’s one of the rare destinations where the golf lives up to every bit of the hype, and there’s a real vacation wrapped around it for whoever you drag along.

Here’s how I’d think about a Kiawah trip.

Quick Facts

• Five public championship courses, plus two private courses: Cassique and the River Course
• About 40 minutes from Charleston International Airport
• Home of the 1991 Ryder Cup, the “War by the Shore,” and the 2012 and 2021 PGA Championships, with the PGA Championship returning in 2031
• The Ocean Course has more seaside holes than any course in the Northern Hemisphere
• Best weather is spring, from March to May, and fall, from September to November
• Gated island, so a rental car is close to essential
• Freshfields Village sits right outside the gate for food, coffee, and shopping
• Charleston, one of the best food cities in America, is about 40 minutes away

Perfect For…

Bucket-List Chasers

If the Ocean Course is on your list, and it should be, this is the trip. Standing on that property where the Ryder Cup and two PGA Championships were decided is worth the trip on its own. The rest of the lineup just makes it a no-brainer.

Guys’ Trips

Five courses, a stack of rental houses big enough for the whole group, and Charleston a short drive away when you want a real night out. Golf all day, then steaks and bars in the city or a low-key night grilling at the house.

Couples and Mixed Groups

This is where Kiawah pulls ahead of a lot of pure golf destinations. The beach is gorgeous, Freshfields has shopping and good restaurants, and Charleston is one of the best food-and-history towns in the country. Non-golfers will not be bored, which buys you more golf.

The Courses

The Ocean Course

 

The headliner, and one of the most famous courses in the world. Designed by Pete and Alice Dye, it hosted the 1991 Ryder Cup and the 2012 and 2021 PGA Championships, and it’s already booked to host again in 2031.

Ten holes run right along the Atlantic, and the wind off the water can turn a good round into a long afternoon in a hurry. One piece of advice: do not play it from the back tees. Move up, enjoy the views, and you’ll have one of the best days of golf in your life. Play it from the tips to prove something and you’ll lose a sleeve and your dignity.

Turtle Point

A Jack Nicklaus design and a genuinely great golf course that gets a little overshadowed by its famous neighbor. The front nine winds through live oaks, then the middle of the back nine, holes 14 through 16, swings out toward the ocean. Some folks will tell you you’re as close to the Atlantic there as you are on the Ocean Course.

Osprey Point

The most player-friendly of the bunch, and a really fun round. Tom Fazio built it around four natural lakes, marsh, and maritime forest, so there’s water in sight on most holes without it constantly being in play. Save room after for the clubhouse, the barbecue there is a legit reason to linger.

Cougar Point

A Gary Player design with some of the prettiest river views on the island, especially through the middle of the front nine along the Kiawah River. The clubhouse is newer and a great spot for a beer and lunch when you make the turn.

Oak Point

The one people skip, and they shouldn’t. It actually sits just off the island on Johns Island, so you pass it on the way in. Clyde Johnston routed it along the Kiawah River and Haulover Creek, it usually plays a little friendlier on the wallet, and you’ll see more wildlife here than anywhere else, gators included. A great value round to balance out a pricey Ocean Course tee time.

The Two Private Ones

Worth knowing about even if you can’t just book them. Cassique, a Tom Watson links-style design, and the River Course, a Tom Fazio layout, are both part of the private Kiawah Island Club and require membership or a member to get you on. If you know someone, beg. If you don’t, the five public courses are more than enough.

Where to Stay

You’ve got options at every level. The Sanctuary is the resort’s five-star hotel if you want to do it big. For most groups, though, the move is a rental. There are a ton of resort villas, and Airbnb and VRBO are loaded with houses on and around the island. Splitting a big rental with the group is the best value, gives you a place to grill and play cards, and keeps you close to the first tee.

Getting Around: Rent a Car

This is the tip that saves your trip. Kiawah is a gated island, and getting an Uber or Lyft to come through the gates, or to find you out there at all, is a real headache. Cars are scarce and waits are long.

Just rent a car at the airport. Everyone in the group should have a way to get around, because you’ll be driving between courses, out to Freshfields, and into Charleston, and you do not want to be stranded behind a gate waiting on a ride that may never show.

Beyond the Golf

Freshfields Village is your home base off the course. It’s right outside the island gate and has coffee in the morning, solid restaurants, and shops for whoever skipped golf that day. It’s the easy answer for breakfast or a group dinner without driving far.

Then there’s Charleston, about 40 minutes away and one of the best food cities in the country. Cobblestone streets, incredible restaurants, rooftop bars, and history everywhere. Build in at least one night in town. The beach is also right there on Kiawah when you need a recovery afternoon.

Pro Tips

• Book the Ocean Course early, especially in spring and fall. Tee times go fast.
• Play the Ocean Course from a forward tee. Have fun, take the photos, skip the suffering.
• Rent a car. Do not rely on rideshare on the island.
• Pair a splurge round on the Ocean Course with a value round at Oak Point to balance the budget.
• Stay in a group rental to save money and have a place to hang at night.
• Log your rounds as you go so you remember which course you actually liked best. I use Golfed for this, since keeping track of where I’ve played is the whole reason I built it.
• Build in a Charleston night. Your non-golfers will thank you, and so will you.

Final Thoughts

Kiawah is one of those rare trips that delivers for everybody. Serious golfers get a true bucket-list course and four more that hold their own. Everyone else gets the beach, Charleston, and a Lowcountry vacation that happens to have great golf attached. Five courses, easy logistics once you’ve got a car, and a setting that’s hard to beat anywhere in the country.

It’s been near the top of my own list for a long time, and once you’ve played it, it’s the kind of place you’ll want to log and remember. Put it on the schedule.

About Golfed

Golfed is a new app for logging every course you’ve ever played. Each course gets a ranking, and you can track your courses against the Golf Digest Top 100, Second 100, and Top 100 You Can Play, broken out by state, architect, and more. It’s built for golfers who care about where they’ve played. Track where you’ve been and where you’re headed, and check Kiawah off the list.

Golfed is free on iOS and Android at golfedapp.com

A guys golf trip sounds perfectly innocent. Four days, some golf, a few steaks, some guys you genuinely like. What could possibly go wrong?

A lot, as it turns out. Not because golf is the problem, but because most guys handle the logistics of a trip the same way they handle everything else – impulsively and without nearly enough communication.

Here’s how to go on the trip and still be welcomed home when it’s over.

1. Don’t Announce The Trip After It’s Already Booked

This is the single biggest mistake guys make. You book flights, you book tee times, you book the rental house – and then you tell her. At that point it’s not a conversation, it’s a notification. She’s not going to feel good about that, and she’s right not to.

The trip doesn’t have to be her idea. It just has to be a conversation she was included in before money changed hands. This is a small thing. Do it.

2. Don’t Pretend It’s “Basically A Work Thing”

It’s not a work thing. You know it’s not a work thing. She knows it’s not a work thing. Framing it as anything other than what it is – four days away with your friends doing something you love – makes it weird and a little insulting.

“I want to go on a golf trip with the guys” is a fully defensible statement that requires no spin. Lead with that.

3. Give Real Numbers

Dates. Cost. All of it. Vague answers (“it’s probably around $1,200 or so, depends on how things shake out”) are worse than real numbers even when the real numbers are higher than she’d like. Uncertainty is harder to plan around than a specific number she can actually evaluate.

Tell her what it costs. Tell her exactly when you’re leaving and when you’re back. She can work with that. She can’t work with “sometime around Thursday.”

4. Don’t Come Home Useless

You had four days off. You played golf, you ate well, you slept in a bed with no one kicking you. Now you’re back.

The dishes don’t know you were gone. The laundry doesn’t care. The kids definitely don’t. Come home ready to be a functioning participant in your own life. If you need 48 hours of recovery time after a guys trip, you did the guys trip wrong.

5. Bring Something Back That Isn’t A Hangover And A Quarter-Zip

You don’t have to spend a lot. A bottle of something she likes, a restaurant reservation for the week you get back, flowers if you’re going to do flowers. The specific thing matters less than the fact that you thought about it.

“I was away for four days and I thought about you while I was there” is a simple message to send, and it does a lot of work.

Here’s the honest truth about guys golf trips: they’re good for you. They’re good for your relationship. Four days with your friends, away from routine, doing something you love – that’s not a threat to your relationship, it’s a deposit into it. Just handle the details like an adult and you’ll be back on the course next year.

Sand Valley is a modern golf mecca in the heart of Wisconsin’s Central Sands, a sprawling 12,000-acre resort near Nekoosa with five world-class courses (plus short options) built on massive prehistoric dunes. That’s so cool you can golf on something considered prehistoric.  True links-style golf far from any ocean. Inspired by Mike Keiser’s Bandon Dunes vision, it features firm/fast fescue turf, exposed sand blowouts, strategic routing, and pure, walkable play amid rolling heathland, wild grasses, and serene wilderness. 

 

Quick Facts

• Five championship courses + short course designs by Coore & Crenshaw,David McLay Kidd, Tom Doak, and a recreated Golden Age classic (The Lido)
• True inland links: Firm conditions, massive dunes, waste areas, blind shots, multiple angles, and creative recovery options, walk-only (caddies available)
• Seasonal play: Mid-May to October for ideal weather (60s-80s°F summers, crisp falls); peak summer for long days, fall for colors and fewer crowds
• Premium resort: Stay-and-play focus with priority tees; top-ranked (Sand Valley & Mammoth Dunes in national top 100 public lists, Sandbox top short courses)
• Pure golf immersion: Minimalist vibe, farm to table dining, trails, lakes for non-golf activities

Wisconsin has so much to offer, more hills than Illinois, cheese curds, delicious beer, awesome golf, and memories you’ll never forget. 

 

Perfect For…

• Guys’ Trips: Multi-round marathons (Sand Valley for strategy, Mammoth for drama, Sandbox for fun), post-golf fireside hangs or patio views, and that high-energy, no-distractions golf focus
• Families: Luxe lodging (cottages, suites), outdoor adventures (hiking, biking, water activities); forgiving short courses; non golfers enjoy nature, tennis, or relaxation

Top Standout Courses

Sand Valley (Coore & Crenshaw)

The flagship. Rolling sand hills with massive exposed dunes, firm/fast fairways, enormous greens, strategic choices, and hidden putting surfaces. Often compared to Sand Hills/Pine Valley hybrids but uniquely its own; a thoughtful, walkable test that rewards imagination and precision.

Mammoth Dunes (David McLay Kidd)

Towering sand features and bold scale,  huge dunes, wide fairways, dramatic elevation, and risk-reward holes with epic views. More power-friendly than Sand Valley but full of drama; a visual stunner with that “wow” factor on every hole.

Sedge Valley (Tom Doak)

Heathland-inspired gem, colorful meadows, thoughtful routing, strategic bunkers, and a shorter par-68 layout for faster, engaging rounds. Subtle yet challenging; provides variety and a nod to classic Old World links in the Midwest.

The Lido (Jim Craig recreation)

A Golden Age revival passionate rebuild of C.B. Macdonald’s lost 1920s masterpiece (once world-class). Timeless strategic test with bold features; exclusive access adds historic magic.

The Sandbox (Coore & Crenshaw, 17-hole short course)

Fun, creative par-3/approach layout, holes 40–140 yards with wild green complexes (double plateaus, lion’s mouth), sand prairie setting. Perfect warm-up, family play, or quick fun; highly ranked short course.

Great Stay-and-Play Resorts & Spots

• Sand Valley on-site, Cozy lodge rooms, suites, cottages with wilderness views; farm-to-table dining, casual bars
• Stay-and-play packages include lodging, rounds (priority/multi-course), practice, and perks. Book early for peak season
• Focus on immersion, walking paths, trails, lakes for paddleboarding/kayaking

All Key Sand Valley Golf Highlights at a Glance

• Sand Valley (Coore & Crenshaw, rolling strategic links)
• Mammoth Dunes (Kidd, towering dune drama)
• Sedge Valley (Doak, heathland meadows)
• The Lido (recreated classic, Golden Age test)
• The Sandbox (17-hole short, fun & creative)

Pro Tips

• Book stay-and-play packages early via sandvalley.com or specialists. Fills fast, especially summer/fall; multi-round discounts
• Fly into Milwaukee (MKE)  2-2.5 hours drive, or smaller airports like Central Wisconsin (CWA)
• Pair golf with Wisconsin favorites: cheese curds, craft beer, farm-to-table eats, or nearby hiking/lakes
• Walk the courses (caddies recommended for strategy); embrace firm conditions and run-the-ball play; forward tees for accessibility

Go experience the rolling dunes of Wisconsin at Sun Valley. You’ll thank me later,

Erin Hills is a world-class golf pilgrimage site, sprawling, links-style masterpiece carved from 652 acres of glacial kettle moraine terrain in Erin, Wisconsin. Conveniently located just outside of Milwaukee. Erin Hills has it all, dramatic elevation changes, vast fescue fairways, perched greens, and natural wetlands/river features. It’s built as if there was always a golf course there. It fits perfectly into the land, paying tribute to mother nature on every hole.

Quick Facts

• One epic 18-hole championship course + Kettle Loop: (5-hole preview/short option) + Drumlin putting course (fun, lit evening putting)
• Minimalist, natural design: Glacially sculpted land with minimal earth-moving, firm/fast conditions, wind play, strategic options, and huge scale
• Walking-only (carts limited/ADA only), enhances the traditional, immersive experience
• Seasonal play: Spring to fall; peak summer/fall for best conditions (60s-80s degrees F); shoulder seasons offer Stay & Play deals
• Elite status: Golf Digest Top 10 public (often #10), Top 50 overall; U.S. Open pedigree and top Wisconsin ranking

Milwaukee is one of the most underrated cities in America. A trip to Erin Hills would give you a reason to experience all Milwaukee has to offer. Great food, Lake Michigan, and immaculate golf. Fun for the boys, fun for the family.

Perfect For…

• Guys’ Trips: High-stakes rounds on a major venue, caddie-guided strategy, post-round chef-prepared meals or drinks overlooking the course, and that “U.S. Open” fantasy vibe, easy to add multi-day immersion
• Families: Charming village-style lodging, relaxed short options (Kettle Loop/Drumlin putting), and scenic beauty; non-golfers enjoy the peaceful setting, dining, or nearby Holy Hill shrine

Top Standout Features

The Main Course (Hurdzan/Fry/Whitten Design)

A modern classic, immense scale with wide fairways, massive bunkers, perched greens, and glacial contours creating endless variety. Risk-reward par-5s, strategic short par-4s (like #2 & #15), and dramatic elevation/wind make it playable yet punishing. U.S. Open host with that “never played anywhere like it” feel, pure exhilaration from 140-yard terror to 620-yard brutes.

Kettle Loop (5-Hole Preview/Short Course)

Carved from the main layout, perfect for late-afternoon quick rounds, warm-ups, or post-sunset fun for overnight guests. Adds replay value and that extra touch of adventure.

Drumlin Putting Course

Lit evening putting green centerpiece, fun, social, and visible from dining/lodging areas. Great for unwinding, family games, or testing green speeds under the stars.

 

Great Stay-and-Play Resorts & Spots

• On-site “village” lodging: Irish Lodge suites (rustic inn charm) or luxurious four-bedroom cottages (private baths, antique furnishings, modern tech)
• Stay & Play packages: Include rounds, reduced/discounted second rounds (especially shoulder seasons like May/September-October), priority tees, resort fee perks (valet, club storage, Caddie Barn access, Kettle Loop golf)
• Chef-prepared dining (breakfast/lunch/dinner with course views), signature drinks, and intimate setting; book direct for best deals

All Key Erin Hills Golf Highlights at a Glance

• Main Championship Course (U.S. Open host, glacial drama)
• Kettle Loop (5-hole short/preview fun)
• Drumlin Putting Course (evening social putting)
• Plus massive practice areas, pro shop, and caddie program (highly recommended)

Pro Tips

• Book stay-and-play packages early via erinhills.com or call 866-772-4769 for season specials (reduced second rounds); fills fast; caddies essential for strategy/local knowledge
• Fly into Milwaukee (MKE), 45-minute drive, easy access from Chicago or Midwest hubs
• Pair golf with Wisconsin classics: craft beer, cheese curds, farm-to-table eats, or nearby Holy Hill views/hikes
• Walk the course (firm/fast means run the ball!); forward tees for fun; embrace wind and natural contours

Time to walk the glacial fairways, channel U.S. Open vibes, and reset on one of America’s elite public treasures. Come to Erin Hills.

The Caddy Shanks Team

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It’s really hard to write this article without doing my world famous impression of Frances McDormand in Fargo. But I’m gonna do my best. Brainerd is Minnesota’s premier golf mecca. A region packed with over 450 holes across dozens of top-rated courses, framed by pristine lakes, dense pine forests, rolling terrain, and that classic “up north” Northwoods escape feel. Home to legendary resort layouts from designers like Arnold Palmer, Robert Trent Jones Jr., Tom Lehman, and more, it’s a stay-and-play paradise with Gull Lake views, family resorts, and endless multi-course options.

Quick Facts

• Hundreds of holes in close proximity, many world-class public/resort courses within short drives
• Northwoods charm: Tree lined fairways, water hazards, elevation changes, and wildlife-filled settings
• Seasonal play: Mid-April/May to October; peak summer/fall for long days, mild temps (60s-80s°F), and prime conditions
• Variety for all: From championship tests to forgiving resort tracks and short courses; stay-and-play packages abundant
• Top-ranked gems: Multiple courses in Golf Digest/Golfweek “Best in State” lists (e.g., Deacon’s Lodge, The Classic at Madden’s)

You know Brainerd is home to a 26 foot tall talking statue of Paul Bunyon. If the amazing golf wasn’t enough to get your tush to Brainerd, I’m sure the Paul Bunyon statue has you chomping at the bit to get there.

Perfect For…

• Guys’ Trips: Epic multi-resort days (36+ holes easy), post-round beers on patios with lake views, friendly competition, and nearby breweries or bonfires
• Families: Resort amenities like beaches, pools, kids’ programs, marinas; shorter courses or par-3s for all levels; non-golfers enjoy boating, fishing, or hiking

Top Standout Courses

Deacon’s Lodge (Breezy Point Resort)

Arnold Palmer’s tribute to his father “Deacon” sculpted through 500 acres of wilderness with rolling hills, wetlands, lakes, and loons calling. Challenging yet playable, nationally acclaimed (Golf Digest top public lists), with dramatic holes and impeccable maintenance.

The Classic at Madden’s on Gull Lake

Upscale championship gem, ranked among the best new public courses nationally, with pristine conditions, strategic design, and Gull Lake scenery. Part of Madden’s 63-hole lineup; a must-play for serious golfers.

Legacy Courses at Cragun’s Resort (Dutch Legacy 27 + Lehman 18)

Modern masterpiece with PGA Tour pro Tom Lehman’s signature 18,stacked sod bunkers, wetlands, wooded sanctuary, and massive renovation/expansion. Dutch Legacy adds variety; 45+ holes total in one spot, rated among Midwest’s top.

The Pines at Grand View Lodge (27 holes)

Joel Goldstrand design with Lakes, Woods, and Marsh nines, a true “player’s course” with challenging variety, blind shots, water, and Northwoods beauty. Highly ranked in state lists; renovated for top conditions.

Pine Beach East at Madden’s on Gull Lake

Historic classic (opened 1926) with Minnesota’s only par-6 hole (over 600 yards!) scenic, enjoyable, and full of character alongside the more modern options.

Great Stay-and-Play Resorts & Spots

• Madden’s on Gull Lake: Classic resort with 63 holes, lakeside lodging, spa, marina, dining
• Cragun’s Resort on Gull Lake: Mile-long beach, Legacy Courses, pools, sports center, cabins/hotel
• Breezy Point Resort: Deacon’s Lodge access, multiple courses, vacation homes/condos
• Grand View Lodge: The Pines & Preserve courses, family amenities, cabins
• Packages include lodging, rounds, carts, breakfast, book direct or via Brainerd Golf Trail sites

All Key Brainerd Golf Courses at a Glance

• Deacon’s Lodge (Arnold Palmer design)
• The Classic at Madden’s
• Legacy Courses at Cragun’s (Lehman 18 + Dutch Legacy)
• The Pines at Grand View Lodge (27 holes)
• Pine Beach East/West at Madden’s
• Whitebirch at Breezy Point
• Plus short courses, par-3s, and nearby gems like Ruttger’s

Pro Tips

• Book stay-and-play packages early via resort sites (maddens.com, craguns.com, breezypointresort.com, grandviewlodge.com) or brainerdgolftrail.com,  multi-course deals save big
• Fly into Brainerd Lakes Regional (BRD) for closest access, or Minneapolis (MSP) 2-3 hour drive
• Pair golf with Brainerd classics: fresh walleye, craft beer, lake cruises, or fall colors
• Use carts for terrain; forward tees for fun; caddies or GPS for strategy on tougher tracks

Get yourself to Brainerd you won’t regret it,

Jesse

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