A Tradewind flight across Long Island Sound to Fishers Island offers plenty of breathtaking East Coast views. But for golf aficionados soaring over the eastern end of the seahorse-shaped island, none are more spectacular than the golf perfection spread out below.

Just off the coast of Connecticut, Fishers Island Club opened in 1926 during what’s considered the golden age of course-building. One of the era’s most brilliant architects, Seth Raynor, designed a dozen-plus courses during this time that are still celebrated today — but you’d be justified to call this one his masterpiece. 

Among the experts echoing this view is Thomas Dunne, director of the Golfweek magazine course-rating panel and co-founder of literary golf journal McKellar. He considers Fishers Island to be “one of the 10 best properties for golf anywhere on Earth.”

There’s a section of the course, beginning with the par-4 4th hole, that Dunne finds particularly inspiring. “To me, it’s the greatest nine-hole run in the world,” he says, “if you combine the natural environment with the excellence of its design and construction.”


Gil Hanse, arguably the most sought-after course architect in the world these days, has played Fishers Island many times and finds it unsurpassed as a combination of stunning visuals and strategic subtlety.

“The first time you play it, you can’t appreciate it architecturally,” says Hanse, who designed the course for the 2016 Olympics in Rio de Janeiro. “There’s too much beauty to take in, too many water views — [the] Atlantic Ocean, Fishers Island Sound, [and] tidal marsh all frame what you see and tend to mask the complexity of the design.”

He’s talking in part about angles of play — the geometry at work as targets are chosen and a player balances risk-reward. “The third hole, a par-4, has an elevated fairway and a green very exposed to the wind,” Hanse says. “If one golfer opted to drive down the right side and his partner hit a drive down the left, they’d basically be playing two different golf holes — and you’ll find strategic variation like that throughout the round.”

You can’t write about a Seth Raynor course without mentioning the design “standards” or “template holes” he so loved. These have intriguing names like Redan, Eden, Punchbowl, Alps, Biarritz, Double Plateau, and Cape. Along with his mentor, Charles Blair Macdonald, Raynor made a habit of including architectural elements that pay homage to beloved golf holes on historic British courses.

Fishers Island embodies that philosophy in fine fashion. It’s even got an Alps-Punchbowl combination — dramatically high mounds guarding a large, bowl-shaped green that will mercifully kick an off-target shot back toward the flagstick.

Considering his legacy, it’s no surprise that there’s even a Seth Raynor Society. It’s administered by Anthony Pioppi, a writer and course expert who recently published the book The Finest Nines: The Best Nine-Hole Golf Courses in North America.


In the name of participatory journalism, Pioppi made the mid-life decision to caddie on Fishers Island for several summers, during which he absorbed the quirks and cadences of life “seven miles from reality,” as he and others have described the island.

“People there are genuinely friendly, and part of that is because everyone crosses paths everywhere,” says Pioppi. “There are two bars — if you count the American Legion bar — and one grocery store. At the checkout counter you’ll see a club member, a waiter, and a grounds crewman in line together, all making casual conversation.”

The need for caddies is based on the course’s extreme walkability. After finishing a hole, you stroll directly to the next tee, steps away. The flow of the round is never interrupted, except by the beckoning views. Pioppi, as a caddie, would encourage first-time players to “put their scorecards away and just settle into the experience.” At the completion of a hole, he might keep his foursome at the green and have them try chips and putts from various locations to fully appreciate the course’s design subtleties and unique challenges.

Part of what’s magical about flying to Fishers is the 36-hole factor. Not that someone arriving and leaving by ferry couldn’t go around twice in one day, but it’s much easier to make that happen when you’ve got air travel going for you. One Connecticut PGA professional, so thankful for his invitations to play the course that he asked to speak anonymously, has a plane-owning, golf-loving friend with whom he’s made the hop to Fishers more than once.

“We go wheels-up around 7 a.m., get on the tee by 8:15, play the course twice and we’re back home for dinner,” he says. “Meanwhile, you feel like you’ve gone back in time when you’re there. Nothing ever changes. There’s tremendous wealth, but the property owners consider the island just perfect the way it is.”


Lest you’re concerned that Fishers Island Club is a golf mecca you’re not destined to visit, there are several charity tournaments open to off-island golfers who wish to support a good cause (while checking off a major bucket-list item). In the springtime there’s a fundraiser outing for the Eugene O’Neill Theater Center in Groton, Connecticut, which is across the Sound from Fishers. Also in the spring, the club hosts an event to benefit Fishers Island churches. This year on September 16, it’s the Next Step Fishers Island Charity Golf Tournament, supporting skill development of young people with serious illnesses. Scouting online, you’ll find rounds of golf at the club included in silent auctions by one charity or another.

Of course, if you do happen to have a friend who’s a member, you’ll be playing for your own good cause: Sublime enjoyment of oceanside golf at its absolute finest.


Tradewind offers private charter flights to Fishers Island year-round. To reserve a charter, call us at 1-800-376-7922 or click here.

All photos courtesy of Anthony Pioppi.