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I know that the older I get I fall deeper into a trap set for me long ago by my maternal grandfather. Grandpa Bastien, that’s what our clan called him. Henry was his given name and what a great man he was. He lived to be 98 years of age; born in 1895. He saw virtually all of the great changes in his lifetime that moved the USA from a farm based economy to one with manufacturing at its core before it then became service centered with families flocking to suburbia. Grandpa Bastien longed for the “good old days” of his youth when things were simpler; bread was 10 cents a loaf; watermelon was sweet and you could change your own oil in the driveway, once you owned a car. I think of him virtually every time I look at a cable TV or cell phone bill or when I am schlepping a case of water from the grocery store to the back of my SUV. I reckon he would have a stroke, right there on the spot, if he knew we were paying so dearly for many of the things we think are necessities of modern life. The idea of checking email or responding to texts would be anathema to Henry. His reality TV was Walter Cronkite.

I think a good number of my contemporaries yearn for a simpler way of life, if even for a few days, or weeks. And while there is virtually no way to escape our day-to-day existence in the wired world, the ability to unplug, unwind and relax are basic ingredients of some big dreams for many. While jetting around the world to experience the glitz and glamour of massive cities like Tokyo or London finds its way on to many bucket lists so do get-away-from-it-all experiences. For many, Sailing fulfills that need to cast away one’s tentacles of modern life and spend some time breathing in salty ocean air while experiencing the timelessness and simplicity of harnessing wind power for propulsion. What was once a necessity for travel and developed simultaneously in different forms all over the planet before the appearance of engines has evolved into a method for returning to our roots all the while learning and practicing the skills of navigation and seamanship. Oh, and you can visit some pretty cool places while you’re unplugging, unwinding, relaxing, learning and practicing.

One area of the world that is ripe with potential destinations for sailing holidays are the 600 plus islands in the Caribbean Sea. Opportunities abound for chartering suitable craft whether the adventurers are new to yachting, have a broad background as a captain, perhaps own their own vessel or maybe understand the basics and just want some minimal assistance. Sailboat Charters that provide everything from the captain and crew and gourmet provisions to bareboat rentals where the only folks on the boat are your friends and family and everything in between are possible.

The British Virgin Islands has been a popular destination in the Caribbean for yachtsmen in search of that perfect on-water holiday for decades. More than 25 land masses make up the archipelago with romantic and memorable names like Tortola, Jost Van Dyke and Virgin Gorda most of which are the remnants of long extinct volcanoes. Deserted white sand beaches, coral reefs, sea cave explorations by kayak and diving wrecks are just some of the favorite pursuits of visitors to BVI as well as sampling the fare at the many upscale restaurants that complement the land based resorts for the occasional diversion from the live aboard. Off most yachtsmen’s beaten path in the BVI,Anegada Island, the 3rd largest in the chain but one of the least visited is a relatively flat coral island (the only coral island in the collection) that has claimed over 300 wrecks in the past several hundred years. Horseshoe Reef, the 3rd largest barrier reef in the world, guards the island along with some of the largest game fish in the Caribbean and prized lobster and conch. Experience matters when sailing around Anegada but the rewards are well worth the effort.

St. Martin is well known jumping off point for visitors to the Caribbean. While many charters from St. Martin head forNevis, St. Kitts or St. Barts, the rich sailing history and secluded escapes of close by Anguilla are often overlooked. Anguilla offers the flavor of the old Caribbean experiences for which so many sailors yearn. Spectacular beaches, wreck diving and an island worth exploring await visitors to Anguilla.

Antigua is one-half of the island nation of Antigua and Barbuda but commands the most visits to its collection of 365 beaches (one for every day of the year). Less-visited Barbuda, requiring a frisky open-water passage, harbors its own treasures with wild horses, frigate birds and long, expansive beaches waiting as rewards for those that make the effort.

The Caribbean islands nearest to the coast of Florida have long been fodder for tales of pirates and plunder; of smugglers and rum-runners. Ernest Hemingway himself liked to unplug in Bimini where many big game fishermen gather to this day to exchange stories and secrets. The lesser known Berry Islands, part of the same chain in theBahamas, has become home to many of the world’s elite where private islands hold their personal getaway homes. At the same time, the Berry Islands still harbor plenty of secluded bays and beaches that provide isolation and access to great snorkeling and diving in an area known as “The Fish Bowl of the Bahamas”.

Exuma Cays, a collection of more than 300 land masses in the Bahamas, protects hundreds of unnamed beaches and coves along with extensive offshore reef areas. Leisurely voyages are the rule while sailing in Exuma whether on the inside passage or outside the Sound.

There are many Caribbean islands just off the beaten path waiting for your exploration that are readily accessible to sailors looking for adventure, for something different or just a place to unplug and spend a few days leading a much simpler life. Using one of man’s oldest forms of transportation to move about in the Caribbean Sea might just be the right way to create those memories that will surely return a smile to your face in the midst of dealing with the frustrations of the modern world.

If you’ve you been on a trip of a lifetime or recently completed an item on your bucket list we’d love to hear from you. Just let us know you are willing to share your experiences with an email to membersupport@tripbucket.com - we’ll take it from there.

Posted by: Craig Loe