A Bermuda Itinerary for the Competitive Traveler

Some people go on vacation to relax. But others see travel as the ultimate opportunity to go hard with high-sport adventure. If you fall into the latter camp—the guy who casually turns beach volleyball into a best-of-seven grudge match—Bermuda may be your ultimate proving ground. It’s not just your standard cocktail-sipping island escape (though, yes, there’s plenty of time for a post-match Rum Swizzle)—it’s also a high-adrenaline playground where you can tee off on championship courses, sail at angles you never knew were physically possible, and join in the merriment of some the island’s beloved pastimes.

So if you’re ready to level up your vacation game, here’s where to compete—and recover—in Bermuda.

For the Golfer Who Wants a Challenge

If you’re the guy who watches golf and thinks, I could make that shot, Bermuda will humble you—in a good way. The island has more golf courses per square mile than anywhere else, none of them nearly as easy as they are picturesque.

For a public course that brings the heat, head to Port Royal Golf Course, home of the annual Butterfield Bermuda Championship. Its 16th hole—a 235-yard par three over a sheer cliff—is where golf friendships and egos are put to the ultimate test. For a hotel-course combo, you can’t beat a stay at the ultra-luxe Rosewood Bermuda. The on-site Tucker’s Point Golf Club offers day passes to non-members, a weekly complimentary golf clinic to hotel guests, and a variety of ways to play. Whether you’re hoping to practice your swing on the range or play the full 18, staff can assist in booking your reservation.

For the Sailor Who Can’t Get Enough of Racing

Bermuda isn’t just good for sailing—it’s the place that literally invented the Bermuda rig, the design used on nearly every modern sailboat. When you race here, you’re stepping into centuries of nautical history.

Serious sailing fans should plan their trip around the Bermuda Gold Cup—then charter a boat with Sail Bermuda to try and match those speeds yourself.

For the Guy Who Knows Cricket Isn’t Just British Baseball

Find yourself more of a spectator? Cricket in Bermuda isn’t a mere sport—it’s a full-blown national event. Consider visiting during Cup Match, an annual two-day competition between St. George’s and Somerset Cricket Clubs that takes place on the last Thursday and Friday before the first Monday in August. It honors Emancipation Day, which marks the end of slavery on the island in 1834. The exciting event includes the main Cup Match showdown, which features all the emotional investment you’d expect from a nearly two-hundred-year rivalry, plus rum tents, food, and live music.

But if your visit doesn’t line up with Cup Match, never fear: Somerset Cricket Club, St. George’s Cricket Club, and others around the island host league matches from June through September.

For the Diver Seeking More Than Marine Life Encounters

Bermuda’s waters contain over 300 shipwrecks, making it the undisputed capital of wreck diving. If you’re here to push your limits, dive the Cristóbal Colón, a Spanish luxury liner that went down in 1936 and is now a massive underwater playground.

If you’re new to diving, you can get the mandated certification at Dive Bermuda, which offers wreck and reef dives for all levels. For the best experience, aim to travel anytime between December and April, when cooler, calmer waters equal better visibility.

For any active vacationer, Bermuda is a playground and a haven, a place to flex your athleticism, test your limits, and leave with more than a few stories, whether about driving a par-four green or cheering on professional-level sailors. This island offers the rare beach vacation where you can leave with both a tan and ego boost—that is, provided you’re as good as you say you are.