Standing at the counter with a cookie in one hand and a chocolate bar in the other, my playing partner, Dylan Dethier, recalled a kid in a candy store. Except he is an adult – and the candy was complimentary. So were the sandwiches. And the ice cream. And the beer. It was near noon on a clear autumn day and we were lounging through a round in a sylvan setting, on glass greens and perfectly manicured fairways winding through corridors of oaks and pines. This was parkland golf at its most pristine, on a resort course that carries the poise and polish of a private club. We were free to walk at our own pace, with no one in sight ahead of us, no one pressing in behind and plenty of room to stop at refreshment stations equipped to satisfy all tastes with sandwiches, savory snacks, craft beers, spirits and sweets worthy of Willy Wonka.
In short, we were playing golf SentryWorld.
In recent decades, Wisconsin has become one of the nation’s premier destinations for the game, home to more publicly accessible Top 100 courses than any other state, including the premier championship appearances of Kohler and Erin Hills, and the minimalist wonders of Sand Valley, Bandon’s Midwestern sibling. But long before that boom, there was SentryWorld, the original spark of Wisconsin golf craze and an essential stop on any Badger State itinerary. Conceived in the early 1980s by then-Sentry Insurance CEO John Joanis as a tribute to the landscape and community that created the company, it was designed by Robert Trent Jones Jr. on a gentle terrain adorned by lakes and mature trees.
Among the standout holes are the cape-style par-5 5th, which boldly wraps around a lake, and the par-3 12th, playing to a green set on a watery peninsula. But none are more photogenic — or more famous — than the Flower Hole, a par-3 surrounded by 50,000 blooms. Jones calls it his “Mona Lisa” — a sign even says so off the tee — and it’s hard to argue with the description: a kaleidoscope of colors in a landscape painting come to life. The hole is replanted every spring, just before Memorial Day, by a crew of 20 to 25 people, who need three days to complete a job that lights up the property all season long.
These factoids were supplied to us by director of golf, Danny Rainbow, about as aptly named an executive as you’ll find in the game. As Rainbow explains, SentryWorld’s appeal lies not only in its conditioning and spectacularly colorful hole, but also in its character – its relaxed, uncluttered pace and sense of welcome that set it apart. “The experience is unlike any other in the state,” he said of the rollout times, park design and culinary oases. “That’s not to say it’s better or worse than other styles of golf course. It’s just a great mix to work with on any Wisconsin golf trip.”
Like the game it celebrates, SentryWorld has never stopped developing. In 2013, ownership doubled in size with a complete renovation and in 2021 opened The Inn at SentryWorld, a beautiful 64-room boutique hotel off the field. That same year, Jones and his team gave it a layout update in preparation for the 2023 US Senior Open. The result is a course that blends resort comfort with tournament rigor—immaculate surfaces (under-air systems hum beneath the greens), 20-minute intervals that make it feel like you have the place to yourself, and those plentiful refreshment stations, a set between the hole 1st and 10th, the other allowing a multiple stop, 33.
When we weren’t stuffing our faces, Dylan and I did a friendly match her. He is a former mini-tour player who still plays with a plus-3 handicap. I’m a six-pointer with a strong swing that makes me look like I’m shooting 100. But I also take a lot of pride in getting shots. Thanks to the flexibility of Jones’ design, Dylan connected it from more than 7,000 yards, while I got it from close to 6,000, an advantage I accepted in lieu of strikes. He still beat me by 1-up – although I like to think I beat him in the calorie count.
If you somehow finish a round in SentryWorld without being well fed, that’s on you. The Library Cafe offers coffee and light bites in a relaxed setting, while PJ’s – a wood-fired bistro with an enclosed bar and breezy patio – caters to heartier cravings. Across the street from the resort, below the Sentry corporate headquarters, Muse serves refined dishes in a space with a nice feel. It’s accessible by lift, hidden behind an unmarked door and adorned with (yes, seriously) Picassos and Calders on the wall.
The next morning, we woke up early and did what any golf lover on a buddy trip would do: hit replay. Another round, another stop (or four) at refreshment stations, capped off by another meal worth remembering. By the time we packed up to leave, the results were clouded, but the impressions weren’t. Golf is a game. But on and off the course, SentryWorld treats hospitality like an art.
“>
