How To Sail Around The Caribbean

By: Maxine Sheppard

August 5, 2010

Onboard chef and accomplished sailor Ayla Lewis follows yesterday’s post on sailing around the Caribbean with a beginner’s guide to chartering your own boat for the ultimate holiday adventure.

In an archipelago famed for its world-class sailing, there’s no shortage of opportunities for even the greenest landlubbers to try their hand at the wheel and feel the wind on their face. There are holiday options to satisfy everyone’s needs, from bareboat charters – which are cheaper but require some experience – to the five-star luxury of a professionally crewed charter yacht.


Best for honeymooners

Start off with a few days onshore at Stonefield Villas in St Lucia, a truly perfect cliff top paradise. The villas, overlooking the ocean from up high in the Pitons, offer complete privacy and seclusion. Then head out for a week aboard a professionally crewed yacht, where you only have to do what you want, when you want.



Stonefield Villas © Stonefield Villa Resort

Stonefield Villas © Stonefield Villa Resort


Exquisite five-star dining, service and sailing will all be tied into one idyllic package, allowing you to cruise wherever the mood (or wind) takes you. Sail ‘down island’ – the term used for going south of the Virgin Islands – towards Grenada and slow down your pace of life.


Best for families

Charter a boat out of the British Virgin Islands. Whatever your budget or experience there will be something to suit, and these islands offer the most protected, sheltered cruising grounds with anchorages being just a short morning or afternoon’s hop from each other.


Fantastic beaches like White Bay Beach in Jost Van Dyke and Smuggler’s Cove in Tortola offer child-friendly shallow waters for swimming. You can also have a go at sailing small dinghies and windsurfing at the Leverick Bay Watersports Centre in Virgin Gorda. These islands attract more sailors than the rest of the Caribbean, but there’s plenty of sea for all.


Jost Van Dyke, British Virgin Islands by Daniel McDonald on

Jost Van Dyke, British Virgin Islands by Daniel McDonald on


Best for adventure seekers

Take off down island from St Vincent to Grenada. The larger islands’ lush interiors offer endless rainforest and waterfall-riddled hikes, while the smaller islands offer secluded white sand anchorages and bays which are perfect for letting life float by.


Sailing in the Caribbean by Anne Oldengarm on

Sailing in the Caribbean by Anne Oldengarm on


The people here love their islands and want you to love them too; you’ll no doubt be approached by friendly locals offering you lobster and fish. Be ready for a true island escape if you head down towards Union Island, Bequia and Mustique though, as shops and restaurants are few and far between. You’ll be rewarded with wonderfully clear waters, immaculate beaches and technicolour sunsets that many visitors never get the chance to see.

A first timer’s guide to choosing a charter

Though the Caribbean sailing holiday itself may be the epitome of tranquility, it does require some careful planning. Important things to consider are:


  • When will you go? The winter months of December to April (the dry season) are preferable for their consistent trade winds, cooler temperatures and lower rainfall.
  • How long do you have? In order to really relax into the Caribbean vibe, it’s best to allow at least two weeks.
  • How experienced is your group? Will you be able to responsibly manage the yacht alone, and do you want to?
  • How many are in your group? Cabins can be ‘cosy’, so if you’re sharing then it’s best if you’re well acquainted.
  • Catamaran or monohull? The obvious advantages with catamarans are speed and accommodation size. What is not so obvious is that they can have an uneasy motion and manoeuvring can be a bit more tricky.
  • What’s your budget? This will influence the size of yacht you can hire, the number of guests in your party, and whether you can afford the luxury of being catered for.
  • What about toys? Does your party enjoy a particular water sport such as fishing, snorkelling, kayaking or diving?
  • How about the cooking? If you’re hiring a skipper, remember that you’ll still be responsible for all the cooking so if you’re after a more laidback trip then consider hiring a cook too.

More information

When you have a fair idea of what you’re looking for, these sites should get you started:


  • Bareboats BVI represents several different charter yacht agents, letting you compare both bareboat and crewed options.
  • Caribbean Sail represent luxurious, professionally crewed yachts chartering across the whole Caribbean.
  • Sunsail and Moorings have large fleets offering bareboat and crewed options.

For the very best fares on flights to the Caribbean, log on to, and read more about Ayla’s recommended sailing highlights in her previous post.


Maxine Sheppard

Maxine is the co-editor of the Virgin Atlantic blog. Travel and music are her joint first loves, and despite having written for Virgin for more years than she cares to remember she still loves nothing more than jumping on a plane in search of new sights and new sounds.

Categories: Our Places