A Pirate’s Guide to the Caribbean




With over 37% of all cruise ships taking place in the Caribbean, it’s no wonder we are seeing more return visitors looking for new ways to explore these gorgeous tropical islands. As countries in the Northern Hemisphere brace for another winter, adventurous travelers begin planning their escapes to warm, sunny beaches. If you are thinking about trying something new this winter, check out this pirate’s guide to exploring and sailing the Caribbean.

Arrr You Ready for Adventure?

If you’ve tried cruise ships and love being on the ocean, perhaps it’s time for you to become captain of your own ship.  No more standing in a cruise ship que waiting for dinner, waiting to disembark, or rushing to return to your ship before it sails without you. A clever new approach to yacht rentals is enabling average Joes and Janes enjoy the sailing adventure of a lifetime. Pick up your very own sailing vessel at one of nine ports in the Caribbean. A wide variety of sea crafts enables you to pick the right size and style of yacht to transport your party in comfort. Experienced sailors can captain their own boats around the islands, creating their own itineraries.

Sailing Adventures for the Non-Sailor

If you’re new to sailing, no problem. You can still sail the Caribbean. Rent a private yacht and hire a captain to skipper your ship or take advantage of a new cabin rental program that is now available on boats sailing out of Tortola, British Virgin Islands. Much like a cabin on a cruise ship, these private cabins feature private baths and full meal service. The advantage is personalized service, no crowds, and being able to sail directly to some of the most beautiful locations in the Caribbean.

Find Your Pirate Booty

Don’t be fooled. The Caribbean is still filled with treasures waiting to be captured. Whether your idea of travel is a cool beverage on a chaise by the water, exploring nature and history, or finding shops full of treasure, the Caribbean has something for you.


Pirates love to discover new destinations. Luckily there is no end of the options in the Caribbean. Snorkel or dive above some of the best coral reefs in the world. Climb through tropical rainforests, splash in waterfalls, and zip line over lush vegetation. History awaits with each island having a unique story to tell. Old forts that guarded sheltered bays from pirates (or for pirates) now provide a trip back in time for those who visit. Walk around brightly colored towns to admire the varied styles of lovingly preserved architecture. Old sugar cane mills beg to be rediscovered and explored. Sail to secluded beaches and enjoy a romantic getaway amongst tropical breezes.

Not-So-Buried Treasure

Aye, we pirates do love sparkly bits of treasure. Fortunately, the Caribbean is still perfect for treasure hunters. Now the treasure is relatively easy to find, thanks to miles of duty-free shopping. The excellent selection of jewelry, electronics, resort wear, and collectables make the Caribbean islands a shopper’s paradise in paradise. Handmade jewelry and the sheer variety of styles, stones, and settings make the islands possibly the best place in the world to shop for jewelry.


Pirates no longer live on bread and water. Sailors now expect to be well-fed on island-grown produce and perhaps the fish you caught that morning. While ashore sample the varied island cuisines. World-renown restaurants pay homage to the hundreds of years of blended cultural traditions that resulted in today’s modern Caribbean cuisine.


No self-respecting pirate would travel without a favorite beverage. Although grog has given way to the aged and rich flavors of rum, the Caribbean is still a pirate’s dream. There is no shortage of boat drinks and flavorful libations to sample on your journey. Don’t forget to check out the wide variety of rums you won’t find back home. A wide diversity in the fermentation, aging, and blending of different brands and varieties of rum means you could spend your entire trip just trying to taste a small portion of the beverages the islands have inspired.

Plan Your Escape

Ready to set sail for warm sandy beaches this winter? Here’s some help to start planning your adventures now. Check out the official tourism Caribbean travel site. The Telegraph’s Caribbean guide provides an overview of when to go and of each of the major islands.