We witnessed the most beautiful landfalls and landscapes in these lush tropical islands known as the Windward Islands. These Islands lie at the southern end of the Caribbean chain and are comprised of Martinique, St. Lucia, St. Vincent and Grenada.

On our sailing voyage, the weather was always a balmy 84 degrees, broken each day by a brief five-minute rain shower accompanied by a stunning rainbow against a lush green backdrop.

Sailing in the deep blue ocean, we saw scores of flying fish and sailed amongst a pod of dolphins that played with the boat for a quiet a while. At anchor, we saw several large Loggerhead turtles and to my big surprise, a large Spotted Manta Ray breached the waters surface with a big splash while we were moored underneath the amazing volcanic spires known as the Piton Mountains.

The sailing was spectacular as we had the infamous Christmas Winds that prevail from December to February. These are reinforced trade winds that blow in the high teens with gusts up into high twenty knot range. These winds are fairly consistent blowing from east to northeast, providing nice beam reach and close reaching sailing up and down the Windward chain of islands. In the channels between islands we found big winds and mature waves as we reached down to St. Vincent.

The boat we sailed on had no problem handling the sea state. “Lollygag II”, a Helmsman 47′, was happily reaching across the large waves with a very sea kindly motion. She is a Danish build, that is likened to a Swan. Set up with a bunch of long-distance cruising features such as solar and wind power, Monitor self-steering windvane, water maker and much more. We learned how to make clean drinking water out of the sea, so water was never a concern. We sat in the cockpit enjoying the flying fish while the windvane steering system, guided the boat flawlessly through the big winds and swells.

This extraordinary sailing destination will definitely give you an unmatched cruising experience of a lifetime!

The trip can be tailored to whatever you would like it to be. The cost is the same whether it is taken simply to gain experience or as an ASA course, varied costs if adding more than one certifications. Food provisions for the boat are bought ahead of time by Captain Ron, and are included in the price, as well as the clearance fees associated with leaving and entering countries. Please feel free to call if you have any questions about the trip’s schedule, planning for it, and upcoming availabilities or group bookings.


Meet the Author, Mary Goff

Sailing School Owner

Mary runs and owns the school, as well as RI Marine Upholstery. Scheduling the classes, assigning the instructors, registering the students, paying the bills, and keeping up with the books is just PART of what Mary does. Her title of “The Mom” better describes her myriad tasks and duties. A USCG Captain, an ASA instructor, and a lady that loves introducing people to the World of Sailing!