Day One: Cougar Point

The first course built at Kiawah Island is the one Gerard would play first. Across 6,814 yards, this Gary Player design, circa 1976, features expansive fairway and greenside bunkers defined by broad flashes of white sand—a unique attribute among the island’s courses. These bunkers often serve as can’t-miss aiming posts and help first-timers better understand the shots they need to hit. The course’s various tee boxes present players of varying abilities with the requisite level of difficulty and challenge. The fourth, fifth, and sixth holes dramatically play right along the island’s protected marshland and, in Gerard’s estimation, compose “one of the most picturesque three-hole stretches” at the resort.

Day Two: Oak Point

Built by Clyde Johnston in 1989, Oak Point flies under the radar of most guests for two reasons: its designer isn’t a household name, and the course is located just across the Kiawah River, on Johns Island. In Gerard’s opinion, this 6,821-yard layout doesn’t get the recognition it deserves, especially considering that it carries the same levels of conditioning and playability as the resort’s four other courses. He also notes that those who venture off island to play it generally like it so much that they immediately want to play it again. “It’s a real shotmaker’s golf course,” he says. “There are multiple risk-reward opportunities, both off the tee and into the greens on the par 5s. And both number nine and number 18 are great finishing holes right along the river.”

Day Three: The Ocean Course

With two rounds under your belt, it’s time to take on the resort’s gauntlet. “There’s plenty of room to play golf on the Ocean Course (main image),” Gerard says. “But Pete Dye was a genius at making golfers feel uncomfortable. Indecision changes a lot, and the wind has a lot to do with that. The wind changes everything at the Ocean Course.” Needless to say, most resort guests who make their way around this major championship layout find themselves grinding to save pars or bogies, which means they too often don’t take the time to appreciate where they are. “You have to stop and take a look around,” Gerard insists. “It’s the perfect setting.”

Day Four: Osprey Point

After a day grinding it out on the Ocean Course, golfers will be clamoring for a reprieve. That’s where Tom Fazio’s Osprey Point comes in, offering up just the type of playing experience that most guests will yearn for one day removed from a round with demanding shots at every turn. Playing around four natural lagoons, the course is widely considered the “favorite” of both resort guests and members, largely due to its wide fairways, generous swaths of rough, minimal forced carries, and approach shots into greens that are generally pretty forgiving and welcoming. “Golfers are just freed up there,” Gerard says, “and they tend to always have a really fun and enjoyable experience.”

Day Five: Turtle Point

Turtle Point encapsulates many of the experiences that golfers will have on each of Kiawah’s four other public courses, making the 6,911-yard Jack Nicklaus layout an ideal conclusion to this bucket-list getaway. Players will immediately notice the fairways here are tighter and, given the many raised, turtleback putting surfaces, the approach shots more daunting. The back nine also delivers a trio of oceanfront holes that rivals the drama and beauty of any stretch of the Ocean Course. Says Gerard, “It’s a great finishing course to your stay.”