The thermometer read 38 degrees when I left my house that morning. Two hours to Cape Cod. I layered up like I was heading to the Arctic—base layer, mid-layer, windbreaker, the works. By the time I pulled into Kittansett Club's parking lot, I looked more prepared for a ski trip than a round of golf.

We had the honor of the first tee time—a privilege bestowed by their longtime head professional, J.P. Connelly, who's been more than welcoming to the Bucket List Series family. As I approached the first tee, still bundled in my layers, our caddy greeted us with a smile. He'd been at Kittansett for 15 years. He was wearing shorts.

I looked at him incredulously.

"Things are about to heat up," he said with a knowing grin.

He didn't mean the weather. He meant the golf.

My playing partner Max insisted we play from the tips—as he always does. Even to my detriment. But that's the beauty of it: we get to see the entire course that way. Every yardage, every strategic nuance, every test Flynn designed. We were joined by a buddy who had flown in for a few rounds—the kind of golfer who casually mentions he's "fresh off a round with Justin Thomas." The next day, he was headed to Wannamoisett, where we had a Bucket List Series event scheduled for October.

"I heard Justin once said his favorite par 3 is the third at Wanny," I mentioned.

He laughed. "His favorite par 3 should be the 6th at Southern Hills (my buddy's home track). In the 2022 PGA Championship he shanked his tee ball, hit a tree with his second, and the ball ricocheted into the bunker. So he blasted out to 20 feet and made the bogey putt. It was a shanky, barky, sandy." 🤣

That's the beauty of golf—even the best in the world have those moments. And that's the magic of courses like Kittansett: they humble everyone, from tour pros to weekend warriors.

Kittansett Club, designed by William Flynn and opened in 1922, sits on a spectacular peninsula jutting into Buzzards Bay. The course is a masterclass in strategic design, where the wind, the water, and the terrain conspire to test every facet of your game. Gil Hanse's recent restoration work has brought back the great character of the course—removing trees to expose the original grassed-over rock formations and opening up stunning views of the bay, especially on holes 2, 16, and 17. Kittansett has a special place in Gil's heart, I'm told. He still consults on updates and improvements, and he's part of the fabric of what makes this place so special.

The opening holes ease you in, but don't be fooled—Flynn was setting you up. Hole 1 shares a fairway with 18, a wide swath of land that demands precision. Hole 2 plays with the wind in your favor, but the beach lurks just behind the green—a downwind shot can find the sand. Then comes the iconic par-3 3rd.

After the 5th hole, as you approach the 7th tee box, you'll find one of Kittansett's most iconic features—and it's not a hole, but a sign. The famous "water level" marker shows the water levels from various storms that have battered Cape Cod over the decades. Hurricane Carol in 1954, Hurricane Bob in 1991, and the "Great Atlantic Hurricane" of 1944 that wreaked havoc along the coastline.

I tried to imagine what water rising 8' 6" above sea level would look like on this tiny sliver of land, and it was easy to feel a bit trapped. I turned around and stared across the fairways surrounded on all sides by the marauding Atlantic. It was a kind of perspective shift that gave me a glimpse at my place in the universe. And I sure felt small. But I realized it was also a humbling reminder that this land belongs to the sea, and Kittansett exists in harmony with forces far greater than golf. That sign is a badge of honor, proof that this course has weathered literal storms and emerged stronger, more revered, and more beautiful.

The par-5 7th looked like a good birdie opportunity. I focused intently on avoiding the cross bunker on the left. Predictably, I caught the edge and rolled right into the middle of it. Golf has a sense of humor.

The par-3 8th is tougher than it looks—with bunkers, tall grass, and mounds providing challenge, plus a devilish two-tiered green. The pin was back right. I left myself a snake of a putt that came up short.

After the 9th hole, we made our way to the halfway house—a nondescript comfort station tucked just past the green. It's got that vintage New England charm: simple, unpretentious, and stocked with exactly what you need to reload for the back nine. I ordered the chicken salad. It was really good—the kind of good that makes you wonder why halfway house food at most courses is an afterthought. At Kittansett, even the small details are done right.

The par-4 10th is a short hole that plays about 330 from the tips, turning around past the halfway house. I hit my best drive of the day—straight into the wind—and still had about 100 yards to a middle pin. An easy par. I felt good.

Then came the par-3 11th. A beast. 220 yards with all manner of hazards protecting the green from interlopers like me. My tee shot found the native grass on the left. A guaranteed lost ball. But my veteran caddy—15 years at Kittansett, remember—knew exactly where it would be. That ball should've stayed lost. A vicious downhill lie in 12 inches of native grass, 80 yards from the green. Any forward progress was the best for which I could hope. It took two more shots to reach the flat stick. A diabolical double.

But somehow I bounced back on the number 2 handicap hole, the par-4 12th. All was right with the world again.

One of the most interesting hole layouts at Kittansett is the par-4 13th, which plays about 355 from the tips. It plays very differently than most holes on the back. The tee shot feels like hitting down a shoot—tree-lined and tight. The hole doglegs hard right, but a strategic bunker on the right fairway forces a left drive, lengthening the hole severely.

But your reward when you arrive at the green? One of the most stunning views in New England. Buzzards Bay wraps around you on all sides. You remember that Kittansett's name—"near the sea"—is like saying Seve had a decent short game. This course is of the sea. And they complement each other perfectly.

The par-3 14th has visual tricks on the tee—the green is obscured and the bunkers hidden from view, forcing you to commit. The par-5 15th is straightforward: hit it straight and hard, with well-placed bunkers making you think on layups.

Then we head back inland through a masterclass of routing that embodies the genius of the Golden Age architects who knew how to get the most from every inch of land. The par-4 16th is wide open and exposed, with a raised green—ride the wind on your tee shot. The par-4 17th plays with hazards dotting both sides of the fairway.

And finally, the iconic par-5 18th. A tempting 460 yards with the clubhouse and the promise of warmth and rest welcoming you home.

Our caddy was right. Things did heat up—not the temperature, but the fire within. Walking those grounds, taking those shots, feeling the history beneath your feet… it lights something in you. This is what golf is supposed to be: strategic, beautiful, challenging, and deeply rewarding. By the time we finished, I had shed most of my layers. The caddy in shorts? He knew what he was talking about all along.

Kittansett Club is more than a round of golf—it's an experience, a story, a memory that stays with you long after you've left Cape Cod. It's quintessential New England golf. It's the kind of course that reminds you why you fell in love with this game in the first place.

The Bucket List Series will open the doors to Kittansett in 2026.

Will you join us where the game takes us next?