Itinerary

The Ultimate Guys’ Getaway in Bermuda

Bermuda has just what you need for an epic guys’ getaway. Just two hours from the U.S. east coast, the island offers spectacular golf courses, incredible on-the-water adventures, vibrant nightlife eye-opening cultural exploration and much more. It’s not all just beaches (though let’s be real, Bermuda beaches are as good as they get)! Get your crew together and get out here for a long weekend. Here’s a three-day itinerary for your ultimate guys’ getaway in Bermuda.

  • Adventure,
  • Friend Getaways,
  • Itineraries,
  • On the Beach
A group of guys are travelling on jetskis.

Day 1

HIT THE LINKS, SIP SOME DRINKS, GET REFRESHED

The island is just 21 square miles – but boasts the highest concentration of golf courses in the world. These courses, located along gorgeous cliffs and coastlines aren’t just beautifully landscaped (and just plain beautiful). They’re also seriously challenging. Port Royal Golf Course’s legendary 16th hole has caused some of the world’s best golfers to send balls flying into the Atlantic.

A man is playing on the golf course.

No matter where your par ends up, you can toast to good friends and great golf afterwards at Port Royal’s classy Bella Vista Grill. The perfect post-golf cocktail? A Dark 'n Stormy®, of course. It’s one of Bermuda two signature cocktails (we’ll get to #2 later on), and it’s a deeply satisfying highball cocktail made with Gosling's Black Seal rum (the dark) and ginger beer (the stormy) served over ice and garnished with a slice of lime. You can also share some tasty appetizers here – everything from chicken wings to panko-crusted wahoo bites (an island specialty).

Bermuda Dark n' Stormy

After you’ve spent the day in Bermuda’s sunshine, perhaps it’s time for a little rejuvenation? Hey, guys need to be pampered from time to time, too – and Bermuda’s many spas offer treatments that will leave you feeling refreshed and ready for adventure.

  • Sports Massage at Natura Spa: Focused around stimulating your muscular, skeletal and nervous system, this treatment will leave you feeling relaxed yet extremely alert. Natura Spa’s setting is amazing, too; it’s located in a centuries-old cave, lit by flickering candlelight.
  • Luxury Gentleman Facial at Newstead Spa: Specially formulated for gentlemen, this anti-aging facial offers exfoliation to help counteract ingrown hairs caused by shaving.

We mentioned that Bermuda has two signature cocktails – the other is the Rum Swizzle. It’s a bravura combo of Gosling's Black Seal rum, orange, lemon and pineapple juices, falernum (local sweet syrup) and a few extra secret ingredients. It might just be the perfect tropical cocktail. Share a jug at the Swizzle Inn, but be forewarned: the restaurant’s motto is “Swizzle Inn – Swagger Out!”

A close up of Bermuda Rum Swizzle with a pitcher and glass on top of a newspaper.

Day 2

OCEAN ADVENTURES

The sparkling turquoise waters that surround Bermuda aren’t just nice to look at. After a hearty breakfast at Bouchée Bistro Français (bloody marys and fruit-topped crepes!), choose your own on-the-water Bermuda adventure.

  • The island is a bona fide deep-sea fishing destination. These bountiful waters are filled with big game catches like marlin, tuna and wahoo. You’ll go home with fish stories to last a lifetime.
  • A jet ski tour of the island is an adrenaline rush like no other. Zoom all over the waters that surround the island and check out otherwise tough-to-get-to gems – secluded beaches, hidden coves and sunken ships.
  • Speaking of sunken ships … is a magical undersea playground for divers. Go undersea to explore such amazing shipwrecks as The Constellation — the basis for Jaws author Peter Benchley’s classic novel The Deep.
  • Charter a boat out to the aptly named Diving Board Island. This is one of Bermuda’s best spots for cliff diving. Take a running jump and make a splash!
  • Take things to the next level aboard an Ubervida sunset yacht cruise on the Great Sound, an exclusive experience if ever there was one. A word of warning, Bermuda sunsets will ruin other sunsets for you for life …
@h2osportsbermuda

After you’ve had your fill of Bermuda’s ocean adventures, hit Hamilton’s Front Street for a taste of Bermuda’s nightlife. Here, you’ll find everything from lively dance clubs like Karma Night Club to laid back sports bars like The Outback Sports Bar at Flanagans). See where the night takes you!

Day 3

ISLAND EXPLORATION

Check out the best of Bermuda's sights, sounds and activities.

Say goodbye to car culture. Rent a motorized scooter or moped and zip all over the island’s winding roads to see the sights, like the frozen-in-time Town of St. George’s or one of the many formidable British forts that guarded the island from invasion back in the day.

Bikes are also a great way to see Bermuda’s best with your bros. A ride on the Railway Trail, an 18-mile pedestrian/bicycle route that spans the island end-to-end. Pedal your way from striking rocky coastlines to breathtaking backcountry greenery.

The fish sandwich is a Bermuda specialty. Many will tell you Art Mel’s Spicy Dish is the best of the bunch – though it’s a hotly contested topic. An ideal lunch option, the sandwich is packed with perfectly fried, perfectly fresh snapper and drizzled with tangy, homemade tartar sauce. Compete with your buddies to see who can finish an entire fish sandwich – it’s harder than you think! 

A person is holding a fish sandwich by the water.

The feeling of discovery is embedded deep in Bermuda’s heritage. Case in point: the incredible Crystal Caves, which lay hidden for centuries … until a Bermudian lost a cricket ball down into a subterranean wonderland. Take a trip into Bermuda’s underworld here, where you’ll find awesome stalagmites and icicles of white limestone and a stunning lake.

Finish your epic guys getaway with a crackling bonfire on Tobacco Bay Beach, a cocktail in hand, celebrating your friendship. Now it’s time to start planning your Bermuda trip for next year …

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