A Photo Tour to Inspire a Boys Weekend in the Cayman Islands

When most guys think of an island vacation, they probably picture lazy beach days brimming with kids, parents and swooning couples – not exactly their ideal scene. Little do they know, the Cayman Islands provides the perfect man-friendly weekend escape. With three unique islands to choose from, including Grand Cayman, Cayman Brac, and Little Cayman, it's easy to spend the week exploring the adrenaline pumping adventure opportunities by day and the endless culinary and cocktail spots by night.

The destination offers everything for men looking for the ultimate getaway with their buddies, from craft distillery tours to active pursuits on both land and sea. Below is a photo tour of the top seven experiences to enjoy on a boys week in the Cayman Islands. 

  • 01 of 07

    Dive Beneath Cayman’s Depths

    Cayman Islands underwater. Sunken vessel
    ••• Cayman Islands Department of Tourism

    Regarded as the birthplace of recreational diving, the Cayman Islands is home to 365 dive sites among the three islands. Whether you’d like to explore the famous Bloody Bay Wall in Little Cayman teeming with colorful marine life or opt for a wreck dive to discover the historic Kittiwake off of Grand Cayman – the destination is a scuba diver’s haven. Not a diver? The Cayman Islands is home to premier snorkeling sites and is a water enthusiasts dream, offering superb conditions for flyboarding, kitesurfing, paddleboarding, fishing and more.

  • 02 of 07

    Try the Local Eats

    Duke's Seafood and Rib Shack
    ••• Duke's Seafood and Rib Shack

    With an array of celebrated chefs, the Cayman Islands, otherwise known as the “Culinary Capital of the Caribbean,” has no shortage of memorable eats. Home to over 225 restaurants – from local spots featuring conch fritters and expertly-seasoned jerk chicken to five-star restaurants featuring best-in-class ingredients – the destination has everything for male foodies to whet their appetite. 

  • 03 of 07

    Be a Night Owl

    Calico Jack's
    ••• Calico Jack's

    Looking to interact with the locals, but also explore the nightlife of the Cayman Islands? Popular clubs for nightlife include Royal Palms Beach Club – a great spot for dancing and live music or O Bar, famous for its acrobatic bartenders. If you’re visiting around the time of a full moon, Calico Jack’s hosts an annual Full Moon party complete with music, different themes, and bonfires.

  • 04 of 07

    Sip on Some “Caymankind” CayBrew

    Alcohol Pumpkin Rum
    ••• Cayman Islands Department of Tourism

    Home to its own brewery, the Cayman Islands’ Caybrew has a variety of lagers and stouts on tap which are ideal for sampling or enjoying beachside. Grand Cayman is also the site of Cayman Spirits Company Distillery, where visitors can savor the destination’s famous Seven Fathoms Premium Rum. Rum connoisseurs can also discover the rare rums of the Cayman Islands at Kaibo’s Rare Rum Bar, which provides guests the chance to sample some of the destination’s most exclusive rums in the form of hand-crafted cocktails or rum flights.

    Continue to 5 of 7 below.
  • 05 of 07

    Live Life Outside

    Cayman Islands
    ••• Cayman Islands Department of Tourism

    Beyond its world-class beaches, the Cayman Islands are also great for adventure enthusiasts looking to stretch their legsWith miles of scenic hiking trails available on all three islands, caving excursions, biking trails, and a chance to see some of the Caribbean’s most beautiful reserves and rare species of parrots, there is no better destination than the Cayman Islands to get the best of both the beach and the woodlands.

  • 06 of 07

    Get Your Adrenaline Pumping Above the Water

    Flyboarding
    ••• Cayman Islands Department of Tourism

    In addition to offering exceptional conditions for snorkeling and scuba diving, the Cayman Islands is also a flyboarder and a kitesurfer’s dream oceanic destination. Little Cayman’s shallow water and trade winds are perfect for kitesurfers of all skill levels. The island’s Southern Cross Club has its own kitesurfing school, Lost Boys Kitesurfing – so whether you’re just starting out or working on some new tricks –  visitors are guaranteed to have their adrenaline pumping as they fly sky high.

  • 07 of 07

    Bring Home the Wahoo

    Cayman Islands
    ••• Cayman Islands Department of Tourism

    Cayman’s waters are abundant with marine life from lobster and conch to lionfish, wahoo and yellowfin tuna – making it the perfect Caribbean destination to sit back, relax and reel in some of the Caribbean’s freshest seafood. With a number of tour operators, fishing tournaments and fishing charters available, men and their buddies can make the most of their “mancation” with an unforgettable fishing excursion.