November 10, 2016 by James Kell

The 5 Most Charming Places In The Caribbean

The Sailing Virgins Caribbean Charm List

"Where are the most charming spots in the Caribbean?"

Sailing for many of us is about exploring cool places. While sailing itself may be great fun, what happens after a great day out is at least as, and much of the time more important than the actual sailing. It's about the destination as well as the journey. For this writer, the keyword is "charm". I want to be charmed by a place. We need to encourage this! That's what this inaugural list is about.

Charm is easy to find in a place like the Greek Islands.  After all, the Greeks basically invented tourism. Herodotus on his wonderings also pretty much created travel writing as a genre. Thanks, Greece.  Go into Pythagorio, anchor-stern-to, walk five metres to a cafe, order an iced cappuccino, life is good. Oh, and the mooring is free btw. Wonderful. Charming.

If the whole charming-places thing rings true with you, and you are considering sailing in the Caribbean, it may not be immediately obvious where to go. For a place to be charming, it needs more than just decent coffee. It needs well-designed buildings. Security. Friendly locals. Basically, it needs to be a place where visitors walk around with a smile on their faces. This can actually be more challenging in the Caribbean compared to say the Med. Ouch. Alas, we say it as we see it. We still love it here. :)

The following places are scored on five metrics. They are beauty, buildings, food, friendliness and security. Please don't hold back on suggestions because you fear it might spoil your favourite place. Sailors do not spoil a place. It is cruise ships who do. So fear not that unearthing your favourite place will make it less charming. It won't. It will simply encourage places to focus on these five metrics.


1. Îles des Saintes, Guadeloupe

This year Îles des Saintes scores the highest on the five metrics. It is beautiful. The buildings are carefully designed, practical and aesthetic. The food is French Caribbean (enough said). The locals are very friendly. And the place oozes with character. The photo below was taken from a restaurant aptly named "Les pieds dans l'eau" (the feet in the water).


2. Saint Pierre, Martinique

If you haven't been to Martinique, do yourself a favour. Scoring a close second to Iles des Saintes as an overall charming island, Martinique has most of what a visitor is looking for. St Pierre, a town in the north, is a great example of what we mean. They have fantastic local markets on a Saturday morning, a crazy volcano story, wonderful couple of restaurants, decent security and locals that are happy to help.


3. Gustavia, St Barthelemy

Commonly known as the Billionaires' Playground, St Barthelemy (aka St Barths) is immaculate without being "too Monaco". Food is great here as might be expected. The best time of year to visit St Barths is in the low season when all the "real people" (ie. employees and small business owners) are roaming the streets and eating at the establishments. Billionaires tend to make good decisions.  They have chosen well in their decision on New Year destinations.


4. Sopers Hole, Tortola, British Virgin Islands

Sopers Hole, part of the West End of Tortola, is a port of entry to the BVI. It is also a quaint, well-planned marina featuring restaurants such as Scaramouche and the Fish n Lime.  Near to Sopers is a little visited island called Thatch Cay. Thatch Cay is a corridor between islands where in November you can sail your boat from east to west and admire the thousands upon thousands of butterflies crossing between the islands. A truly trippy experience.


5. Bequia, The Grenadines

Once a boat building hub of the Caribbean, Bequia has given itself over to relaxed sailing tourism. Surrounding islands such as Mustique and Union also help to give the Grenadines its fine reputation for cruising. Most locals are truly friendly. Bequia is certainly a place worth visiting.


Notable mention goes to Little Harbour, Jost van Dyke, BVI. Strawberry is a lovely local lady and runs a restaurant there called Sydney's Peace & Love. You can stern-to your (shallow draft) boat to her dock. With an honour-bar system, her chef also makes simple yet very decent local fare. The only thing Little Harbour lacks is a bit more traffic (never thought I'd say that) to keep it interesting.

The above list mentions five of the most charming parts of the Caribbean. This is bound to be somewhat controversial (we hope!). Your author has spent the past while sailing in and around the eastern Caribbean with the adventure sailing school Sailing Virgins.

If you are interested in a sailing adventure where you can also receive your skipper qualification, get in touch with us. If you have some experience and would like to receive your skipper qualification, we run week-long fast-track skipper courses in the Virgin Islands, endorsed by the ASA through Virgin Islands Sailing School. Click here to learn more about the Fasttrack to Bareboat Skipper ASA 104 Program.

If you would like us to send you a free pdf of the BVI and a sample sailing route, please press below and leave your contact details. And if you have comments on your favourite place in the Caribbean, we'd love to hear from you!

Free PDF - BVI Islands Map / Sailing Route


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