By Captain Davis Jones

Have you ever considered a sailing vacation in the Caribbean? It sounds adventurous and out of reach for many, but with the right planning and a good crew, it can be an exotic, yet easy way to escape the winter blues, soak up some sun, enjoy the beautiful waters, and travel around the islands without being restricted to a hotel. My first trip was to the Virgin Islands in 2002 leading a Sea Scout trip and have been back many times since. In fact, a later trip to the BVIs was the first time I sailed with Capt. Andrew and Andrei long before we started our partnership on Shardana.

Crew Selection

The first step is to create a compatible crew. Most boats will fit 6-8 people, but it can get a little crowded after a few days if you don’t all get along. Not everyone has to be a sailor; an experience Captain and a few people who know what to expect are essential, as assisted by the pampered passengers. Just like on Shardana in the Chesapeake, I’ve sailed the Caribbean with people that have never been on a boat (including my then 6-year’s old daughter), Sea Scouts getting their first ocean experience, Shardana friends getting ready for their own bareboat experiences, and old salts with forty-years’ plus experience.

The Virgin Islands

The next step is to decide where to go. The British and U.S. Virgin Islands are a sailor’s paradise; I’ve been there three times. Fresh breezes, clear water, a protected channel, and line-of-sight navigation make it a perfect first-time trip. An easy flight into Tortola or St. Thomas and/or a short ferry along with a cab ride gets you on your boat in no time. You’ve probably heard of Pusser’s (not the one in Annapolis), Foxy’s (not the one in St. Michael’s) and the Soggy Dollar Bar, and now you’ll get to see the originals, not our Chesapeake copies. At Norman Island, on which Robert Louis Stevenson based his book “Treasure Island”, you can see “The Dead Man’s Chest” from the lyric “15 Men on a Dead Man’s Chest—Yo, Ho and A Bottle of Rum”. But the natural beauty of the islands is outstanding. Finding your way through the rocky path to The Baths or hiking up to the top of Virgin Gorda are both breathtaking walks, in their own way. The low-island of Anegada with it surfable beaches and lobster dinner is worth the off-shore sailing. Anegada has the 3rd largest coral reef in the world and is a scuba divers playground. Speaking of scuba diving and snorkeling, the BVIs have everything from the world famous “Indian Rock” Formations, the Wreck of the Rhone, Salt and Peter Islands and multiple other sites. Book a dive with a local shop and they’ll pick you up at your boat for day under the waters you’ve been sailing across. You might even run into a local celebrity; I said hello to Richard Branson when he came into Virgin Gorda for a bike ride (his private island isn’t that big) and Bernie joined us for a dive.

The Bahamas

The Bahamas is another “easy” destination. In March 2021, we got a 42’ catamaran and sailed around the Abacos with a crew of 8 ranging from 3 to 56 years old. Belight (the boat) had a little more room than Shardana, and sailed flat, which the little kids and new sailors appreciated. The Bahamas was still recovering from Hurricane Dorian while dealing with Covid 19 very carefully. We had to show our tests before arrival and had to get tested while there. It threw a little wrench in the sail plan as we had to wait in Little Harbor for the clinic to finish with checkups for all the babies on the island before the nurse would let us in for testing.

Antigua to Dominica

Antigua is another great destination for either coastal sailing around the island or as a launch for offshore adventures. You can sail around Antigua and Barbuda or use it as a launch to go “explorer cruising.” Andrew, the crew, and I launched from there to head south as far as Dominica. In Dominica we hiked and swam in very secluded waterfalls. I believe that Dominica is the most beautiful Island in the Caribbean and want to spend more time ashore. On the way, our friend David caught a 10 lb. Mahi-Mahi which fed us well for the next few days. Despite my lack of sleep and long flights, the overnight sail in 30 knots of wind was exhilarating and set a great tone for the trip. As we were led into Dominica the next morning by our self-assigned “Boat Boy”, Andrew spotted a boat in the mooring field he recognized. Sure enough, he had taught the new owner/captain his ASA Sailing course back in New Jersey! He then purchased a boat and decided to go cruising. Small world – never know who’s going to catch you. After too few days in Dominica, we island-hopped our way north to Isle de Saints through Guadeloupe, where we snorkeled and dived a world famous reserve established by Jacque Cousteau on Pigeon Island, then turned north to head back to Antigua. A walk around Nelson’s Dockyard and English Harbor made me harken back to the days of sail and to lust for a job on a 200’ wooden sailboat but had to fly home.

Grenada and the Grenadines

Grenada and the Grenadines was another wonderful trip island hopping with spectacular diving, swimming with the turtles in Tobago Cays then enjoying a lobster dinner, visiting the traditional boat building yard in Carriacou, exploring Bequia—the only country allowed to hunt 1 whale a year to maintain their culture. Bequia is also famous for their scrimshaw (carvings from whale bone; Bequia is the only place you can purchase it legally) as well as their model coconut boats. One of the highlights was when Mr. Fabulous took us for a lobster bake on a little spit of an island (after swimming with the turtles). Great dinner and dancing in the sand (Shut up, Andrew!)

Anchored Behind a Reef So We Can Snorkel

Now pick the boat…

Now that you’ve decided where to go, what do you sail and how do you get the boat? Catamarans are big and comfortable; no doubt about it. But they don’t move through the water like a traditional, monohull sailboat, and usually cost about 30% - 40% more than a comparable monohull. You do see a lot more catamarans in the Caribbean than in the Chesapeake, despite our shallow waters.

There are multiple charter companies depending on where you go, what you want, and how much you want to pay. Most companies have both monohulls and catamarans, and you can find something for just about any date if you book early enough. I’ve sailed with Navigare, Horizons, and Sunsail, and have a new relationship with Waypoints in the Virgin Islands. All offer reliable, comfortable, and well-maintained yachts with appropriate support before and during your trip. It is simpler than ever to see what’s available when you want to go and compare prices to get the best deal possible.

How much is all this going to cost?

That is hard to set a figure because much depends on the time of year, location, and number of people on the boat. The 42’ catamaran I used for my last trip in March 2021 for 8 people to the Bahamas was a little over $6000. February pricing for the BVI could be as little as $5800 to over $25,000 for a 50 foot catamaran. In March I am leading a trip to Thailand where four of us are each paying $1,145 for a four cabin monohull. Additional expenses include airfare, captain, food and drink for a week.

If this sounds interesting, contact me, davis@shardanasailing.com to discuss details and expectations for your trip. I will assign you a Captain (often me but not necessarily). Your captain will work with you to plan your trip, find an appropriate location and boat, Captain the boat, and make your dreams a reality. You don’t have to wait for summer to make your next sailing story!

Sail Your Story in the Caribbean