Guide to Caribbean sailboat rental: 5 West Indies yacht charter tips

Oct 01, 2021 BY Luke Rees

Looking to sail in the Caribbean but don’t want to be on a boat full of strangers? Then you should read this guide to Caribbean sailboat rental and the five West Indies yacht charter tips below.

Guide to Caribbean sailboat rental 5 West Indies yacht charter tips Flickr CC image by Cowbell solo9

Why sailing in the Caribbean?

The Caribbean Islands is known for great weather, white sandy beaches and blue-turquoise waters. It is often described as paradise by landlubbers, but due to reliable trade winds this is even more true for sailors wishing to explore it’s 7000+ islands, cays and reefs.

Sailing the West Indies is fairly easy, meaning Caribbean sailboat rental is possible for people who would not do so elsewhere. This is due to easy conditions and most islands being less than 20 nautical miles from their neighbours. Although coast guard services are lacking so always sail prepared for the worst.

The politics and national division of the Caribbean is not simple. There are many independent nations plus overseas collectives usually with European ‘motherlands’. All of this means there is huge ethnic diversity among the islands. Carib indigenous, African, French, Dutch, Portuguese, Indian and British – to name a few.

The beauty of Caribbean sailing holidays is how flexible they are. You can have a quiet relaxing time in paradise, mooring in deserted coves and barely seeing other people. Or you can visit many great harbours so enjoy excellent food, frequent festivals and fun times.

Guide to Caribbean sailboat rental 5 West Indies yacht charter tips pixabay royalty free image from antigua

Guide to Caribbean sailboat rental

Winter and spring are probably the best time to charter a yacht in the Caribbean. The east-northeast trade winds are a reliable 12 and 22 knots from December through to April with minimal storm squalls.

You can of course sail in the West Indies all year round and off-peak does offer cheaper prices. However, it is hurricane season from June to November (worst months September and October) so it can be hit or miss. That said, most islands do not get hit each year so it is potentially a risk worth taking.

Whenever you visit the main thing to note about sailboat rental in the Caribbean is you have a lot of choice. From the Bahamas to Barbados, Saint Martin to Saint Lucia and Guadeloupe to Grenada you can charter a yacht and set sail on circular routes or one way journeys. The choice is yours!

5 West Indies yacht charter tips

This guide to Caribbean sailboat rental would not be complete without some tips to choosing the right charter. There are certainly a few things to consider before booking your boat.

Guide to Caribbean sailboat rental pixabay royalty free image from antigua

Type of sailboat

The first decision is what kind of boat will be most suitable for your trip. The main decision comes down to size, but you also need to choose between a traditional yacht, catamaran or gulet. Each is slightly different and has its own advantages.

Skippered vs self-sail

If you are new to sailing, inexperienced or out of practice, you should charter a sailboat with a qualified skipper. In some countries the law permits sailing without a licence, but a lot can go wrong and having a boat captained by a pro makes life a lot easier.

Crewed vs un-crewed

Depending on the the experience of the rest of your party and their willingness to get involved you may also need a crew. A large boat can be a lot of work to handle and a crew helps things run smoothly. You can also make it more relaxing and luxurious if they handle the cooking and cleaning etc.

Learn to sail

If you are helping out on the boat you will of course learn the ropes while on sailing holidays. However, you can make this official by chartering a yacht that includes sailing lessons. This is a great way to combine a vacation with learning a new skill.

5 West Indies yacht charter tips pixabay royalty free image of sailing in antigua

Where to go

This is probably the toughest decision you’ll have to make. For most people it makes sense to start and end at the same island. But there are so many to choose from…

I recommend you read this article about the best Caribbean ports for sailing holidays to help you decide. Alternatively book the cheapest most convenient flight and take it from there.

We hope you found this guide to Caribbean sailboat rental useful. Find out more about yacht charters in the Caribbean here.

Caribbean, Caribbean Sea
Sailing, Yacht Charter
Independent Travel
Travel Articles

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