Illustration by Adam Larkum

Gulfshore Explorer


Gulfshore Explorer: A Run at SWFL’s Most Daunting Holes—in One Day

If there were an official sport of Southwest Florida, you’d have to assume it would be golf. We have more holes here per capita than any other place on Earth. That’s not to say I went everywhere on Earth and counted golf holes. That’s just what I’ve been told, and I have no real reason to doubt it. In fact, there are so many golf courses in the area that people here actually live on them.

Nevertheless, what makes golf one of the greatest sports is that you can be terrible at it, scream obscenities and have a full tantrum meltdown, and still be willing to spend tens of thousands of dollars a year on a membership just so you can do it as often as you like. Well, that and it’s pretty. You aren’t going to find a better-looking, more tranquil spot. You can also drink as soon as you’re finished—or earlier, as some courses have bartenders with mobile carts who will serve you alcoholic beverages while you’re out playing. Let’s see kayaking try that .

But I thought it might be nice to see why golf in Southwest Florida is such a big deal. And with us deep in the heart of reciprocals season (where private clubs let members of other clubs come play and hang out), I decided to play nine of Southwest Florida’s most challenging and/or picturesque holes in the span of one day.

It turns out that’s a horrible idea. From one end of Collier County to the other end of Lee County is a day trip unto itself. And, perhaps unsurprisingly, you actually can’t play just one hole of golf and then leave. They frown upon that. So, I guess what I’m saying is don’t try this at home unless you’re a fancy magazine columnist like I am.

To be honest, I assumed the real challenge would be picking the holes. After all, there are an estimated 250-plus country clubs between the two counties, and several of those have multiple courses. Add to that the number of public courses and, well, I decided I would leave it to fate. That means I asked friends and experts where they thought I should go. I got some good options.

Near the top of the list was Hole 16 at Calusa Pines Golf Club in Naples. I love courses that don’t have home sites on them, and Calusa Pines is a gorgeous step into what nature could have been if God didn’t rest until Day 8. The course was actually designed by Michael Hurdzan and Dana Fry, and they put this hole on a pedestal. Almost literally. It feels like the highest point in the State of Florida and requires actual golfing skills in order to avoid a wonderfully picturesque pond and bunker on the right and some trees and shrubs to your left. PGA legend Rocco Mediate once called this hole one of his favorites in the entire world. It’s one of mine as well.

Just 23 minutes away in the tony Grey Oaks, my friend Dante DiSabato (a Realtor and golfer extraordinaire) suggested I hit Hole 17 of the community’s Pine Course. The course itself was named one of the “Top 5 Toughest Private Golf Courses in Florida” by Florida Trend magazine. And I’ll tell you why it’s hard: I mistakenly stopped by the pool café prior to teeing up. All I’ll say is that they make a mean drink at the bar. Which reminds me, why is it that Arnold Palmer is the only golfer with a drink named after him5? Surely we should all be drinking a Jack Nicklaus or a Tom Watson. But I wouldn’t order a Sam Snead just because it’s snard to snay. Regardless, you really should try 17 of The Pine. (And the club sandwich. Yum.)

And speaking of quality food and beverage, Pelican Marsh Golf Club just finished renovating its clubhouse (it renovated the actual course a few years ago), so that’s a great place to wine and dine after a round. I just swung by because I’d heard good things about its par-5 finishing hole (not the bar) and wanted to give that a try. It’s a deceiving dogleg to the right, and I was lucky enough to hit it during a quiet moment between some shootouts. The course was the host site of the 2018 U.S. Open Qualifier and the PGA Pro-Am in April. It hosts the South Florida Pro-Pro next month (July 7-8). Nevertheless, it turns out my unenviable slice came in pretty handy with this dogleg, and I successfully maneuvered my way down the fairway without killing anyone. My second shot also featured my slice prominently and splashed down in the massive water hazard that takes up a majority of the right side of the fairway. But, I hit again from the same spot and it bounced its way to the edge of the beautiful undulating green. A quick wedge and a steady putter put me in in four.

A quick beverage at the beautiful clubhouse and I raced to what might be the most stunning location for a golf course in all of Florida: South Seas Island Resort, at the north end of Captiva Island. The resort has a fairly simple nine-hole design, but what makes it amazing is that its water hazard and sand trap happen to be the Gulf of Mexico and its beaches. Several of its holes literally run alongside the Gulf. Unfortunately, only guests can play the course, but why not make a reservation and chill out for a few days while driving some balls on the beach? Best of all, the sunsets are mindboggling. If I ever see the green flash while holding a golf club, I’ll assume that’s the universe giving me a hole in one.

But the afternoon was winding down, and I wanted to move beyond these fancy country-club and resort courses, if only to see how the other half lives. It turns out that one of the most challenging holes of golf in Southwest Florida is also on one of the busiest courses between Tampa and Miami. Eastwood Golf Course, one of Fort Myers’ two city-owned courses, recently renovated its front nine with the help of golf course architect Steve Smyers, who also designed several other area courses, including TwinEagles (The Eagle course) and The Fort Myers Country Club. Golf Digest ranked Eastwood one of the Top 100 Public Golf Facilities in the U.S. for 10 straight years until the magazine switched to a star rating. There’s no question that the course is busy7. That front nine has too many angry angles to discuss here—the entire thing is insanely close to water or bunkers or both—but suffice it to say if it weren’t for former USTA pro player and coach Mark Davis, I would have been left weeping by the monstrous water hazard of Hole 3. You need to know what you’re doing there. I didn’t. And there really isn’t a clubhouse to drown my sorrows, so I just got a bottle of water out of the vending machine and felt bad about myself. Wow, golf is great!

Is that nine holes? I don’t think so. But I think it’s best that I just head home, pop Caddyshack into the VCR and pour myself a tall, cool Tiger Woods. Hold on a sec while I just back the Escalade out of the driveway..