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

Every golfer I know either has been to Hilton Head (and raved about it) or wants to go to Hilton Head. It is America’s premier golf island, a lowcountry paradise with over 26 championship courses, framed by pristine beaches, live oaks draped in Spanish moss, marshes, lagoons, and endless Atlantic views. From iconic PGA TOUR hosts like Harbour Town to oceanfront gems and strategic parkland layouts, it’s year-round golf heaven with mild temps, Southern hospitality, fresh seafood, and that relaxed island vibe.

Quick Facts

• Over 26 championship courses, designed by legends like Pete Dye, Jack Nicklaus, Robert Trent Jones Sr./Jr., Rees Jones, Davis Love III, and more
• Lowcountry style: Tree-lined corridors, water hazards, marsh views, wind, and strategic shot-making
• Year-round play: Mild winters (60s-70s F), warm summers; best in spring/fall for prime conditions and fewer crowds
• Price variety: Greens fees $100-$400+ (peak season premium); stay-and-play packages offer big savings
• Home to the RBC Heritage PGA TOUR event at Harbour Town Golf Links

Seriously, Hilton Head is one of the most popular golf destinations in the country, and it deserves to be. It offers something for everyone. Whether it’s a trip with the buds or a vacation for the family, Hilton Head won’t disappoint.

Perfect For…

• Guys’ Trips: Multi-course days (easy to hit 36 holes), post-round cocktails with ocean views, friendly bets on signature holes, and island nightlife or beach bonfires
• Families: Resort beaches, pools, spas, kids’ programs; forgiving options and short courses; non-golfers enjoy biking, kayaking, or exploring the island

Top Standout Courses

Harbour Town Golf Links (Sea Pines Resort)

The icon! A Pete Dye masterpiece with Jack Nicklaus input, host of the RBC Heritage. Tight fairways, tiny greens, bulkheads, overhanging branches, and the famous red-and-white lighthouse on 18. Precision over power; pure strategy and history.

Atlantic Dunes by Davis Love III (Sea Pines Resort)

Seaside stunner, rebuilt from the island’s original Ocean Course with coquina shells, native grasses, dunes, and Lowcountry charm. Beachfront par-3s, dramatic closing stretch; NGCOA National Course of the Year winner.

Heron Point by Pete Dye (Sea Pines Resort)

Risk-reward classic with mounding, swales, fairways shifting toward and away from hazards. Challenging yet fun with multiple tees; Audubon Sanctuary certified for natural beauty.

Robert Trent Jones Oceanfront Course (Palmetto Dunes)

Oceanfront drama with shifting winds and an elevated par-5 10th green right on the Atlantic. Memorable views, challenging yet rewarding; consistently top-ranked in South Carolina.

Arthur Hills Course (Palmetto Dunes)

Unique and strategic, with rolling terrain, water, and bunkers; one of South Carolina’s top public layouts with great conditions and variety.

Great Stay-and-Play Resorts & Spots

• The Sea Pines Resort: Harbour Town, Atlantic Dunes, Heron Point; villas, Inn & Club luxury, beaches
• Palmetto Dunes Oceanfront Resort: RTJ, Arthur Hills, George Fazio courses; oceanfront villas, pools, tennis
• Other highlights: Port Royal (Barony/Robber’s Row), Oyster Reef (Rees Jones), Hilton Head National

All Key Hilton Head Golf Courses at a Glance

• Harbour Town Golf Links (Pete Dye, PGA TOUR host)
• Atlantic Dunes by Davis Love III (seaside Lowcountry gem)
• Heron Point by Pete Dye (risk-reward beauty)
• Robert Trent Jones Oceanfront (Palmetto Dunes, Atlantic views)
• Arthur Hills (Palmetto Dunes, unique strategic test)
• George Fazio (Palmetto Dunes, toughest par-70 on island)
• Oyster Reef (Rees Jones, lagoon/marsh drama)
• Plus off-island value like Old South Golf Links

Pro Tips

• Book stay-and-play packages early via resort sites (seapines.com, palmettodunes.com) or specialists like Golfbreaks; includes priority tees and multi-round deals
• Fly into Savannah/Hilton Head International (SAV), 45-minute drive
• Pair golf with Hilton Head musts: fresh seafood, shrimp and grits, biking trails, beaches, or the RBC Heritage if timing aligns (April)
• Play mornings to beat winds; use carts; forward tees for fun; caddies add strategy on Dye classics

If Hilton Head isn’t golf mecca, we don’t know what is. Head down to South Carolina and enjoy all it has to offer.

The Caddy Shanks Team

Life moves slower on the island, and this is your perfect time to get down there and reset. Kiawah Island is a world-class golf paradise off South Carolina’s coast, a private barrier island with 10 miles of pristine beaches, maritime forests, marshes, and five championship resort courses at Kiawah Island Golf Resort. Designed by legends like Pete Dye, Tom Fazio, Jack Nicklaus, Gary Player, and Clyde Johnston. It’s bucket-list territory: oceanfront drama, wind-swept links-style play, wildlife (alligators included\!), and that perfect Lowcountry mix of challenge and beauty. Home to the 1991 Ryder Cup (“War by the Shore”) and multiple PGA Championships. It’s a place of Legends

Quick Facts

• Five championship courses, all public/resort-accessible, recently renovated with Paspalum greens for superior play
• Coastal challenge: Wind, water, bunkers, and ocean views on many holes; elevation subtle but strategic
• Year-round play: Mild winters (great escape), best shoulder seasons (spring/fall) for calmer winds and temps (60s-80s°F); summer mornings beat the heat
• Luxury access: Stay-and-play packages at The Sanctuary Hotel or villas/cottages; priority tees, caddies available
• Top-ranked: Ocean Course consistently \#1 in SC (Golf Digest/Golfweek); others in top resort/public list

This is a good time to remind everyone that Alligators are dinosaurs. Dinosaurs that live among us. Apex predators in our backyard\! Terrifying and beautiful. Don’t get too close.

Perfect For…

• Guys’ Trips: Epic multi-course days (Ocean for bragging rights, others for variety), post-round cocktails at the clubhouse or Sanctuary, beach bonfires, and Charleston nightlife nearby
• Families: Resort beaches, pools, spa, kids’ programs; more playable courses like Cougar/Osprey; non-golfers enjoy biking, kayaking, or wildlife tours

Top Standout Courses

The Ocean Course (Pete Dye)

The undisputed legend, host of Ryder Cup 1991, PGA Championships 2012 & 2021. Seaside links masterpiece with 10 holes along the Atlantic (most in Northern Hemisphere), massive waste areas, wind as a major factor, and diabolical greens. Often called one of America’s toughest and most beautiful.

Turtle Point (Jack Nicklaus)

Nicklaus redesign (2016) with narrow corridors, strategic water, and a thrilling three-hole ocean stretch (14-16) through dunes along the Atlantic. Challenging accuracy test with hidden hazards; beautiful finishing holes and ocean breezes make it memorable.

Osprey Point (Tom Fazio)

A Fazio masterpiece, blending natural lakes, marshes, and maritime forest, playable variety with stunning landscapes, large greens, and wildlife sightings (ospreys, alligators). Ranked highly for women and groups; serene yet engaging.

Cougar Point (Gary Player, renovated)

Dramatic marshland layout along the Kiawah River, generous fairways, risk-reward par-5s, vast greens, and water everywhere. Playable for all levels with gator sightings and scenic river views; great for confidence-building rounds.

Oak Point (Clyde Johnston)

Lowcountry gem meandering through ancient oaks, undulating fairways, and river/creek views, strategic and scenic, demanding thoughtful play over power. Underrated beauty with 4.5-star acclaim.

Great Stay-and-Play Resorts & Spots

• The Sanctuary at Kiawah Island Golf Resort: Forbes Five-Star luxury oceanfront hotel with spa, pools, dining
• Villas & Cottages: Spacious private options (including Ocean Course Cottages); ideal for groups
• Packages bundle lodging, rounds (Ocean upgrades), breakfast, carts. Book direct for best access

All Key Kiawah Island Golf Highlights at a Glance

• The Ocean Course (Pete Dye, iconic seaside beast)
• Turtle Point (Jack Nicklaus, ocean stretch drama)
• Osprey Point (Tom Fazio, marsh & forest beauty)
• Cougar Point (Gary Player, river marsh playability)
• Oak Point (Clyde Johnston, Lowcountry classic)

Pro Tips

• Book stay-and-play packages early via kiawahresort.com, or specialists (Premier Golf, etc.) Ocean Course tee times competitive, especially peak seasons
• Fly into Charleston (CHS), 45-minute drive; easy access
• Pair golf with Lowcountry classics: fresh seafood, Charleston historic tours, beaches, or wildlife spotting
• Respect the wind (play mornings); use caddies for local tips; forward tees make Ocean manageable for mortals

Get yourself a slice of that Southern charm on Kiawah Island,