Sailing in The Caribbean: From St. Maarten to The British Virgin Islands

Half a year ago now I spent a night sailing from St. Maarten to the British Virgin Islands (BVI). Sitting in the cockpit, gazing at the stars I wrote this post but never got round to publishing it… until now:

Here I am, just before midnight, on the lookout on a catamaran that we are sailing from St Maarten to the British Virgin Islands. A ‘delivery’ they call it in this world of sailing that’s completely new to me.

Yacht deliveries can happen for a number of reasons (new owner, owner who wants to have his yacht moved, special maintenance, etc) but in this case we, my skilled sailor friend and I, are moving this yacht because the company managing it and renting it out needs it in the BVI.

sailing from st maarten to tortola, BVI

Behind me I’ve seen the bright lights of the densely populated island of St Maarten and the more subtle orange glow of the quieter island of Anguilla disappear. And in the far distance, I can see the lights of Tortola, one of the British Virgin Islands.

With only a gentle breeze and a comfortable Caribbean temperature it’s quite relaxing actually. Ok, I do realize that I should look out for small fishing boats that could theoretically appear out of nowhere but for now, it’s just me, the stars and a luxury 40-foot catamaran…

Also read: Want to Sail Around The World? Here are 7 Ways to Make it Happen!

With the sails up and this light wind we are going at a steady 8 knots, slower than your average cyclist maneuvers through traffic in Amsterdam, but at the perfect speed to enjoy pure tranquility… moving forward in this dark, moonless night as if you are the only one left on earth…

How Did I End Up Sailing in the Caribbean?

Life can take you interesting places sometimes!

How did I get here? With no sailing experience and no money to rent a boat like this I guess you could say by chance.

But by chance I’ve done a lot of amazing things over the years and if I speak to other expats or digital nomads (people who spend a large part of their life traveling and living abroad) they equally have a long list of exciting experiences.

So I think this is one of the things that comes with choosing a less standard lifestyle: you get to see so many different ways of life from up close and tonight it’s the life of a sailor who has been asked to deliver a boat to the British Virgin Islands…

Also Read: Traveling For Life – What It’s Like to Move Country All the Time

I literally jumped on the boat this afternoon at 4.30pm, after a long day at work and in a hurry to make it to customs to clear out and be able to start this mini-adventure. Because by 8pm tomorrow I’ll be on a plane back to St Maarten, ready to go back to my day job the following morning.

Also read: Top Things to Do in St. Maarten & What to do in St Maarten if You Visit on a Cruise

But for now I’ve got an exciting trip and a completely new experience ahead of me. According to the screen in front of me (the one I should be watching instead of typing this) we will be arriving to the BVI just after 6am tomorrow morning. Then we’ll probably go for an early morning swim in what’s supposed to be amazingly clear water, try to stop by one of the main islands Virgin Gorda and maybe even see if we can sail past Richard Branson’s Necker Island.

I already know that after that I’ll start to feel slightly uncomfortable as we head for Tortola, where we have to deliver the boat and where I will feel I have to pretend I understand this sailing world that is so unknown to me…

Ah well, for now I only have to make sure we don’t sail into a fishing boat and enjoy the stars and the amazing trip…

Life is what happens to you while you are busy making other plans, right?! I definitely never planned to deliver someone’s catamaran from one Caribbean island to the next!

What an amazing trip this was… The following morning we spent exploring a few of the islands and, by chance, swimming with a wild dolphin that seemed to be craving some attention and stayed around the bay we were in, literally circling around us, for over half an hour! Truly unique!!


About the British Virgin Islands

Sailing, diving, fishing and soaking up the sun on perfect beaches is what it’s all about on the 60 idyllic British Virgin Islands. Largest island Tortola, home to capital Road Town, is a 12 by three mile (20 by 5 km) haven of white sand and lush green mountains.

Where Are the British Virgin Islands

The British Virgin Islands (or BVI), is a British overseas territory located in the Caribbean to the east of Puerto Rico. The islands make up part of the Virgin Islands archipelago; the remaining islands constitute the U.S. Virgin Islands and the Spanish Virgin Islands.

The British Virgin Islands consist of the main islands of Tortola, Virgin Gorda, Anegada, and Jost Van Dyke, along with over fifty other smaller islands and cays. About 15 of the islands are inhabited.

The islands have a population of about 28,000, of whom approximately 23,500 live on Tortola.

The BVI are a popular travel destination for sailors, fishermen, sun worshippers, and other independent travelers, albeit not for the cost-conscious.

Many who want to go sailing in the Caribbean choose the BVI. Boating among the dozens of tiny, mostly uninhabited, islands is incredible!

With steady trade winds, calm currents, protected bays and pirate-ship bars, this is one of the world’s sailing hot spots.

A tropical climate tempered by easterly trade winds, relatively low humidity and little seasonal temperature variation make the weather in the BVI rather enjoyable.

The islands were first settled by the Dutch in 1648 before being annexed in 1672 by the British. The US dollar is the legal currency within the British Virgin Islands. The islands of the BVI are highly dependent on tourism, generating an estimated 45% of the national income, together with the offshore financial industry.

Best Time to Visit the British Virgin Islands

A good time to visit the British Virgin Islands is October to November, after the worst threat of hurricane season and before the crushing crowds of the winter holidays. Plus fall room rates on these expensive islands are the lowest you’ll find all year.

Scuba divers should plan a trip for winter and spring; the summer is the worst time for visibility underwater. Avid sailors should try to visit in March, during the BVI Spring Regatta.

Thinking about visiting the Virgin Islands? Check out the Beginner’s Guide to Island Hopping in The Virgin Islands

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Sanne Wesselman

Author: Sanne Wesselman
A traveler, wanderer, digital nomad, and entrepreneur. Owner of marketing company A to Z Marketing.
I spend most of my time living and working abroad and use this website to share "the good, the bad and the ugly" of traveling and living abroad. Visit the About Me page for more info.

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