Kiawah Island, SC

The 2nd year of the East Islip crew's annual Ryder Cup trip sent us to Kiawah Island in South Carolina. In 20121 the East Islip crew's Ryder Cup officially became a tradition. Year two is always the make‑or‑break year—you either cement the ritual or let it fade—and there was no better place to lock it than at Kiawah Island. Most of us were still grinding through entry‑level jobs at the time, so rolling up to Kiawah felt like we’d suddenly leveled up in life. And thanks to my cousin Harrison working his magic, we somehow landed a tee time on the Ocean Course. That’s the kind of favor you don’t forget; without his connections, the combination of limited availability and premium pricing would’ve kept us on the outside looking in.

We made the trip in late October, running back the same Ryder Cup teams from Tucson: Funk, Dog, Curt, and Kyle vs. Keith, Tom, Kip, and Alex. The first 2 days we played 2v2 Best Ball at The Ocean Course and Turtle Point. Then the last day we had our singles matches at Oak Point. The good guys came in with something to prove after the bad guys’ dramatic comeback the year before, and the stage at Kiawah couldn’t have been better for a little redemption arc.

We played the Ocean Course in full survival mode. The wind was ripping at 30‑plus mph, the rain was coming in sideways, and our caddies were practically begging us to take a rain check. But we only had three days on Kiawah, and there was no universe where we weren’t teeing it up. We showed up in shorts, half‑functional rain gear, and the kind of blind optimism only a boys trip can produce. We didn’t care. We were buzzing. Winning our matches and soaking in the beauty of the course were the only things on our minds.

And honestly, playing the Ocean Course in the elements felt fitting. This is a place built to be shaped by wind—Pete Dye designed it so that almost every hole is exposed to the Atlantic, and on a calm day it’s already one of the toughest tracks in the country. Add a storm and it becomes a different sport. Every shot felt like a negotiation with the weather. Drives ballooned and hit on par 3's, wedges got knocked out of the sky, and putts wobbled like they were rolling across a trampoline. But even in the chaos, the place was stunning. The dunes, the ocean views, the way the course seems to rise and fall with the coastline—it all hits you at once.

We were drenched, but it was the kind of round you remember forever, not because of the scorecard, but because you played one of the world’s great courses on its terms, not yours. The Ocean Course is absolutely worth the price of admission for any trip to Kiawah.

The teams split points: 1-1 on day 1.

Day 2 took us to Turtle Point, and the golf gods finally cut us a break. After getting slapped around by the Ocean Course in a full‑blown storm, stepping onto Turtle Point under blue skies felt like we’d been transported to a different trip entirely. Warm sun, a light breeze, and a course that was far more forgiving—at least visually—made for the perfect reset.

Turtle Point has this calm, classic Jack Nicklaus feel to it. It doesn’t punch you in the mouth the way the Ocean Course does; instead, it eases you in with tree‑lined fairways, clean sightlines, and a rhythm that builds as you move through the round. But the real magic happens at the finish. The closing stretch runs right along the ocean, and we caught it at the best possible moment—late afternoon, sun dropping toward the water, the whole sky turning gold.

Those last few holes were golf heaven. The light was perfect, the ocean was glowing, and every swing felt like it belonged in a commercial. After the chaos of Day 1, it was the kind of round that reminded us why we travel for this stuff. Pure vibes, pure scenery, and the perfect way to set up the final day of the Ryder Cup.

The Good Guys swept both best‑ball matches, giving us a 3–1 lead heading into the final day. After the heartbreak of the previous year, it felt like the perfect setup for a full redemption arc.

Day 3 took us to Oak Point, the lone course off the main Kiawah property, though you’d barely notice thanks to the resort shuttles that ferried us around all weekend. The setup actually worked perfectly—Oak Point was on the way toward Charleston, where we were gearing up to spend Halloween night, so the logistics couldn’t have lined up better.

Like Turtle Point, we caught another picture‑perfect day. Oak Point doesn’t get the same hype as the Ocean Course or Turtle Point, but it deserves just as much love. The layout winds through marshes, lakes, and live oaks, with a handful of holes that sneak up on you in the best way. The par‑4 18th is the one everyone talks about—a sweeping finishing hole framed by water that forces you to pick a line and commit. It’s a strong closer and a great stage for Ryder Cup pressure.

The matches were tight all day, and the teams ended up splitting the points. That was all the Good Guys needed. After the heartbreak in Tucson and the grind of the Ocean Course, we sealed the deal and took home 2nd annual Ryder Cup victory.

The cost of the trip—three nights in a massive on‑property mansion plus rounds at the Ocean Course, Turtle Point, and Oak Point—came out to roughly $1,700 per person on the low end. That doesn’t include airfare or our night out in Charleston, both of which added their own damage. What did make the price feel worth it were all the intangibles that came with staying on Kiawah. The resort’s shuttle service made getting to and from every course seamless and gave you the freedom to enjoy the Ryder Cup bar at The Ocean Course, which a must for any boys trip. The house itself was enormous—everyone had their own bedroom, and the living room turned into the perfect post‑round headquarters for watching football and recapping the day. And when we wanted to level things up, The Ocean Room delivered one of the best steakhouse dinners any of us had ever had.

Looking back, the only real miss was the golf volume. We only played 54 holes, which we quickly realized is the bare minimum for a Ryder Cup trip. If we could redo it, we’d squeeze in at least another nine each day or try to get out on Cougar Point, which was a tease while we enjoyed our cocktails from the Players Pub (another must). Lesson learned for every Boys Ryder Cup going forward: more golf is always the right answer.

Price for Golf & Lodging: $$$