Best Destinations to Sail to in the Caribbean

I am sailing,

 I am sailing,

 Home again,

‘Cross the sea

I am sailing,

Stormy waters,

To be near you,

To be free

            Rod Stewart, 1988


But where is “Home again”? Where does one go “to be free”?

Sailing is an interesting sport making the answers to these questions interesting and difficult. They are not the same answers for everyone. Sailors have at least two things in common: First, they are naturally adventuresome. But secondly, and most importantly, they are not bound by someone else’s vision of home or being free. They are mostly bound by their own independence. They don’t like being told where they must go, or when. That, among other things, is what makes them sailors.

On the other hand, the adventuresome side of their being draws them to ports unknown, stormy seas or no. They listen to other sailor’s stories, always looking for new adventures. If they hear of a port in the storm that sounds mysterious or just a little edgy, they are immediately drawn to it, like a moth to a light. It is a challenge.

So I asked. I asked noted sailors to give me the favorite ports in the storm, centered in and around the Caribbean for simplicity. Where do they look forward to going, and why? What draws these sea-faring moths to those lights in the storm? The list is intriguing, and in no particular order.

San Juan, Puerto Rico: Full of dark alleys and mystic. There is danger around every corner. The city attracts the adventuresome, and notable, interesting people.

Gustavia, St. Barth: Very small and very French. Known for great French foods and wonderful wines. Vilas are cheap to rent so there will be in interest in extending your stay.

Charlotte Amalie, St. Thomas: Of interest to numbers of sailors because it is easy to get to, close to the US Virgin Islands. The island is known for their wonderful residents with fewer than the normal number of tourist for a Caribbean port.

Philipsburg, St. Maarten: A classic Dutch community, with a strong Dutch culture. There exists a very strong European feel about the village, with wonderful hospitality.

Fort-de-France: Known the world over for their spice crop. The aroma that permeates across the island is in itself worth the trip. Mix the intoxicating spice mix with the best rum in the Caribbean and it makes all else less important.

Falmouth, Jamaica: This Island is off of the beaten path but well worth the trip, especially if you are interested in reggae music. The alleys are crammed with juke joints that feature great food and wonderful music all night long.


And there you have a summary of wonderful ports that attract sailing enthusiast the world over, each looking for his or her own brand of freedom, and a new place to call home. As every travel agent around the world would say, “Come see us, the weather is wonderful, the water is clear, the rum is free flowing, and who knows….this could be the home that sets you free!”           


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