I first wrote this article while crewing on my first yacht delivery, saling from St Maarten to the British Virgin Islands (BVI). With practically zero sailing experience.
I’ve since bought a catamaran and sailed the Caribbean extensively, so I’ll add some more practical sailing tips at the end. But I love my somewhat naive, inexperienced views as well, so I’ll leave the start of the article as it was originally written.
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.

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 light winds 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 7 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 to the BVI?
Life can take you interesting places sometimes!
How did I get here? With no sailing experience and no money to charter 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 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 4.30 pm, 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 8 pm 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 we will be arriving at the BVI just after 6 am 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 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! We spent the morning exploring a few of the islands in the BVI and, by chance, swam with a wild dolphin! The dolphin seemed so curious and stayed around the bay we were swimming in, literally circling around us, for over half an hour! Truly unique!!
Tips for Sailing From St Maarten to the BVI
1. The Simpson Bay Bridge
If you are departing from the Simpson Bay Lagoon to sail to the BVI, keep in mind that the Simpson Bay Bridge breaks, regularly.
Believe me, I’ve lived in St Maarten long enough to see it break several times and to hear a lot of complaints from boaters.
If you are on a tight schedule you might want to consider anchoring outside the lagoon the night before you plan to leave, just in case.
In any case, you can find opening times for the Simpson Bay Bridge here.
2. St Maarten Versus the BVI
If you are still deciding which Caribbean islands to sail to and you’re not sure if you can fit in both St Maarten and the BVI, then pick the BVI.
Since I first wrote this article I have bought a catamaran and sailed around the Caribbean myself. And although I love St Maarten and think there are some great things to do on the island, the BVI has more to offer as a sailing destination.
The BVI has countless islands to explore, most of which lie extremely close to each other. St Maarten doesn’t have that. And although St Maarten has a sizeable boating community as well, the BVI has a larger community and is better set up as a sailing destination.
3. Chartering a Boat in the Caribbean
If you are looking to charter a boat in the Caribbean, I’d recommend checking Click&Boat because of its large and diverse offering.
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 39,000, of whom approximately 24,000 live on Tortola.
The BVI are a popular travel destination for sailors, sun worshippers, people who love fishing or scuba diving, and other independent travelers, albeit not for the cost-conscious.
Many who want to go sailing in the Caribbean choose the BVI. Cruising 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 early November to early December, after the worst threat of hurricane season and before the crushing crowds of the winter holidays. Plus room rates on these expensive islands are the lowest you’ll find all year.
Or, if you love regattas, try to visit around the end of March, during the BVI Spring Regatta.
Scuba divers should plan a trip for winter and spring; the summer is the worst time for visibility underwater.
Also read:
- Sailing in St Maarten – Anchoring in Mullet Bay
- Sailing in Saint Lucia: Everything You Need to Know From Anchorages to Safety & More
- A Complete Sailing Guide for Grenada, West Indies
- Do You Want to Sail Around The World? Here are 7 Ways to Make it Happen!
- The Best Caribbean Destinations & Why
- 7 of the Best Diving Spots in the Caribbean
This article about sailing from Sint Maarten to the BVI contains an affiliate link. I may receive a commission for purchases made through this link, at no additional cost to you.