Sailing the Caribbean, A Trip of a Lifetime

Have your ever dreamed of sailing around the Caribbean Sea on your own sailboat? Can you picture yourself alone, with your partner, or close friends gliding on the turquoise and emerald waters? Believe it or not this dream is not far fetched at all. I’m sure only a small percentage of us would feel confident […]

Have your ever dreamed of sailing around the Caribbean Sea on your own sailboat? Can you picture yourself alone, with your partner, or close friends gliding on the turquoise and emerald waters? Believe it or not this dream is not far fetched at all. I’m sure only a small percentage of us would feel confident enough of our sailing and navigation abilities to take on such an adventure but the fantasy does not have to end there. The Caribbean is a sailor’s playground, composed of over 5,000 islands, reefs and caves combined with line of site sailing and some challenging open water experiences. White secluded sand beaches, studded with coconut palms, picture perfect harbors alive with splashes of island colors and a plethora of activities, make sailing the Caribbean a most a memorable experience.

Many companies throughout the Caribbean islands provide crewed boat rentals via catamarans or single hulled vessels. The boats usually come with a captain and mate that double as a chef. Catamarans have two hulls connected by a bridge deck and provide great stability. They don’t lean or “heel” and travel at twice the speed of single hulled boats. Their speed enables them to explore more places in the usual 7-10 days rental time frame. Many live aboard catamarans offer sailing conditions that just don’t get any better providing an unforgettable adventure; both unique and personalized. They are perfect for families traveling together and especially several couples traveling together.  Chartering a sailboat can also be very economical for couples sharing the costs of the rental. Average rates run from the $250 per person/per day range including 3 gourmet meals a day. Family experiences speak for themselves with treasured memories lasting a lifetime.

Several of my local friends embarked on this kind of adventure in celebration of a 60th birthday! They chose a week in the month of April to take advantage of the beautiful weather and to avoid the hurricane months of June through October. Some of the islands also schedule sailing regattas during the spring months, making it even more appealing to catch a glimpse of that. My friends flew to the US Virgin Islands where they transferred to the BVI (British Virgin Islands) and met up with their boat and captain with “Island Life Charters”, but there are many of them. They had previously discussed their itinerary and food preferences with the captain via email. Their boat was a 50 ft sloop-rigged catamaran with 4 well appointed state rooms, each with its own private en suite bathroom, including electric toilets, shower and vanity. The stateroom also had air conditioning and power outlets. The cabin windows opened to capture the sweet Caribbean air providing perfect temperatures for sleeping.

Exploring the catamaran revealed an open layout. There was a gourmet galley and bar/seating and large cockpit area next to captain’s chair. This area was used for eating and relaxing. Additional relaxing space was provided on the bow of the boat. My friends had decided on a combination of exploring the many beaches providing swimming and snorkeling, and a chance to relax. The scenery is absolutely gorgeous. They also chose to visit the little towns that dot the islands. They spent 2 days anchored off the island of Jost Van Dyke , home of the famous “Foxy’s Beach Bar’ and restaurant; a destination within itself and one of the most famous hangouts for sailors in the region. The BVI have some of the most perfect waters in the world for sailing with the added feature of almost never being out of site of land as you sail between the islands. This can also help with any seasickness, unlike a large cruise ship that often spends days at sea with no land in site. This is very reassuring for first time sailors!

The itinerary varied among the islands of St John, Virgin Gorda, Tortola and Peter Island along with the previously mentioned Jost Van Dyke. They also sailed past some of the privately-owned islands including Necker owned by Richard Branson, founder of Virgin Atlantic Airways and Curt Richardson, founder of Otter Box protective covers for cell phones. Sailing captains are a close-knit fraternity which has advantages over large cruise ship vessels. Aside from a more personalized, intimate experience you can also avoid the crowds when island hopping because the captains frequently know the schedule of the shuttles and save moorings for one another so you can get in and out easily for island exploring. My friends spent their days snorkeling the caves inspired by “Treasure Island” as well as beautiful coral reefs. They relaxed, hiked and toured many of the locations.

Their captain was also very knowledgeable about the history of the island and told many great stories. One of the outstanding experiences for them was stopping at Bathes, a bizarre Jurassic jumble of monumental boulders piled along the shore. Filled with caves and title pools that added to the other worldly experience they swam and bobbed/floated amongst them.

Unlike large ship cruising and an all-inclusive resort stay, a Caribbean sailing vacation is a quintessential escape from the grim, gray upstate NY winters. While a resort or cruise ship may offer more amenities, nothing can take the place of standing on the bow of your ‘own’ boat gazing up at the stars. The stars are so close and clear you feel you can reach out and touch them. Eating delicious personalized meals with some of the seafood caught right from your own boat and thinking about what a unique, transformational experience way to visit the Caribbean. If you ever have the opportunity, jump aboard, unwind, unplug and enjoy this adventure in paradise!

Let’s face it, traveling can be exciting, life changing and transformational for families of every age. As 70 becomes the new 50, 60 the new 40 and 50 the new 30, family members are more active than ever right now and enjoy traveling together. Travel is one of the most rewarding gifts parents and grandparents can give to their children. Whether exploring the world far from home or staying together at a nearby resort or camp it creates a chance for everyone to get to know each other and share and create lasting memories and powerful bonds that money can’t buy.

Traveling with your grandchildren or adult children does not have to be limited to theme parks or beaches or cruises, although all of these can be options. Family vacations can include cabin rentals in state or national parks; vacation home rentals on or near the beach; houseboat and RV rentals, ranch stays, bicycle trips, cruises and of course those all-inclusive resorts. These are just some of the family vacation options. We definitely cannot leave out the traditional American favorite vacation—the road trip in the family car or van, even if it dredges up memories of the hilarious Chevy Chase film “National Lampoon Vacation”!! Regardless of which type of vacation is considered, it must be tailored to your specific budget and goals.

Learn more about this catamaran charter at https://www.islandlifecharters.com/











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