The Caribbean By Boat: How to Charter Your Own Yacht

By: Chantelle Symester

August 12, 2014

There’s something a bit jet set about doing the Caribbean by boat. The idea of chartering your own private yacht and sailing into the sunset is an alluring thought most of us only dream of. But for those up for the adventure, planning a trip and chartering your own yacht isn’t as difficult, complicated or as expensive as you may think. But before you rush off to live out your Robinson Crusoe fantasies, here are a few pointers to bear in mind:

Who to charter from

Anchored yacht | Caribbean by boat
Opt for a luxe boat and anchor up in tranquil waters © Els van der Gun/istock/Thinkstock

The first question to ask is what kind of boat are you after, although if you want to look like an insider technically a boat in nautical terminology is a submarine. The first big decision to make is steam or sail, so to speak. A yacht or a motor yacht (aka a gin palace)?


Where’s the best place to start? Well, surely it has to be with those sleek, beautiful, classic wooden yachts from a bygone era, after all you want the rest of the port to sit up and take notice when you arrive in harbour. Classic charters, based out of Antigua, has a stunning range of yachts some of which were built more than a century ago. These titans of sail mostly come with a crew so team members can kick back and relax a little.

If you’re after something a little more modern (and reasonably priced) then companies such as Sunsail and The Moorings come with a good range of catamaran, monohulls or motor yachts for you to make a choice from. Most of the boats come equipped with all mod cons from electronic navigation to flat screen TVs, air conditioning and BBQs.


Finally, if you have Russian oligarch ambitions want to charter something really special that comes equipped with its own helicopter try luxury yacht broker Edmiston.

To bareboat, or not to bareboat

At helm of yacht | The Caribbean by boat
Why not take the helm of your own yacht and try your hand at bareboating © David de lossy/iStock/Thinkstock

It may come as a surprise to some but you don’t actually need any certification to charter your own boat and you can get your hands on a 50ft beauty without much in the way of documentation. A short assessment and Q&A session will soon determine whether you can spend your trip bareboating (sailing without a trained skipper on board), island hopping across the Caribbean by boat. On the flipside if you prefer to leave the technicalities to someone else and spend the holiday with a glass of rose and a grilled lobster, most chartering services can provide a trusty and experienced skipper to take you to some of the most spectacular coastal stretches in the world. Once you’ve decided on whom to charter a boat from, you can get to the fun bit of deciding where to actually sail to.

Novice and intermediate sailors can also choose to go on a flotilla holiday – here a group of boats, all ‘bareboated’ will sail in convoy so that help is always on hand if something goes awry and there is more of a party spirit.

Where to go

If you are after some truly staggering marine life head to Grenada where sailors can leap off the yacht into pristine waters surrounded by a multitude of coloured fish, hawksbill turtles and even some wrecks. If you’re after a little bit of peace and quiet head to Carriacou Island (about 40km north of Grenada) or alternatively Clifton Harbour Union Island is the major yachting hub of the southern Grenadines and you’ll be greeted by an energetic marina filled with great restaurants and a lively bar and club scene.

Grenadines | Caribbean by boat
Grenadines is a great destination to experience the impeccable marine life © Medioimages/Photodisc/Thinkstock

Dubbed luxury yacht charter capital of the Eastern Caribbean – Antigua is much loved by the sailing community because of its large bays and harbours, extraordinary beaches and coves, and close proximity to neighbouring islands.  Among the most popular harbours on the island is The English Harbour and nearby Falmouth Harbour, both of which are locations where a number of key events are held including the highly anticipated Antigua Yacht Show.


If you want to go further afield, there is a reason why the British Virgin Islands are a favourite among sailors. The calm waters make it an easy and enjoyable journey and there are plenty of idyllic spots to anchor down and go for a dip in the cool blue seas. The only downside is that during peak season is does get busy. Around March/April each year the BVI Spring Regatta and sailing contest takes place. Here over 100 yachts gravitate to the picturesque isle for one of the Caribbean’s biggest sailing events.

Yachting | Caribbean by boat
Planning your own yachting trip needn’t be stressful © AngieDawson/iStock/Thinkstock

When to go

For obvious reasons chartering your own boat should ideally be scheduled outside of Hurricane season, which runs from June to November, unsurprisingly it is also the rainy season and while it is sailable (and you’re more likely to get a bargain) there is the risk of some serious storms especially in August, September and October. You will need to check forecasts and plan for any eventuality, although it is very rare for yachts to be caught up in hurricanes.

Sailing boat yacht regatta race on sea | Caribbean by boat
Catch one of the big sailing regattas that take place during the peak season © StevanZZ/iStock/Thinkstock

The busiest tourist sailing season occurs in the winter months – December through to May when many want to escape to sunnier climes. There are a few big sailing regattas during this time; so die-hard sailing fanatics will want to conveniently organise a trip to coincide with them. The Antigua Sailing Week usually takes place around April/May each year, and attracts thousands of yachts from all over the world. The traditional Regatta – Guadeloupe to Antigua Race – remains a highlight of the festivities and see if you can bag yourself a start number or a berth in a professional racing yacht.

The annual St Maartin Heineken Regatta, which starts in early March, is also another favourite among avid sailing enthusiasts. As one of the largest Regatta’s in the region, the Heineken Regatta sees over 200 entries across 32 different countries.  And when you’re done with sailing, you can let your hair down at one of the parties held each night on the island.

Header image: Explore stunning locales like Green Cay located in the British Virgin Islands © digital vision/Photodisc/Thinkstock

Virgin Atlantic operates direct flights to the Caribbean from London Gatwick. Book your flight today.

Have you explored the Caribbean by boat? Would you ever consider chartering your own yacht? Share your thoughts with us in the comments section below.

Written by Chantelle Symester


Chantelle Symester

Chantelle Symester is a writer and editor based in London. When she’s not chained to her laptop working she can be found hopping on a plane to far flung places across the globe. Trips so far include adventures to Mexico, South America and North Africa and she now has her heart set on discovering the East. You can find her @csymester

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