6 Steps to the Ideal Caribbean Yacht Charter Holiday


How to plan your ideal Caribbean trip

The sun-blushed Caribbean is a fantastic yacht charter destination, with consistent trade winds, sensational sea life, warm waters and even warmer people. From the Grenadines' spice islands to the Bahamas' swimming pigs and Belize's untamed jungles, this diverse sea includes some of the world's foremost sailing and an abundance of land-based delights.

There are many charter bases littered along the island chain, and it can be hard to know where to start. One thing's for sure, you'll never be short of options.

Our guide takes you through the 6 steps to planning a superb Caribbean yachting holiday, tailored to fit you.

Browse Caribbean yacht charters here

Caribbean top tips

Friends On A Boat

Step 1

Gather your crew

Perhaps the hardest part of planning any holiday is getting your group together. Finding the right fit of personalities is important, as you’ll be spending a lot of time with these people.

Head off on a romantic break for two, grab a gaggle of buddies, or spend quality time with your nearest and dearest.

Whatever you choose, the size and make up of your group is an important precursor to choosing the right yacht for you and your group


Step 2

Choose your dates

Once you’ve decided who’s coming, the first thing you’ll need to do is figure out when you want to go. There are many factors involved here, from school term dates to optimal seasons to visit each region and island.

The Caribbean is blessed with perfect sailing conditions almost all year round, which gives it an enviable flexibility you can’t find in other sailing areas like the Mediterranean. That said, there are optimal times to visit each island, from the BVI to Antigua, which vary depending on location.

Naturally, you’ll want to avoid the worst weather. Thankfully, the Caribbean has a reasonably predictable Hurricane season, which usually runs from late August, through September to early October. There is even a useful mnemonic to help remember this: June too soon, July standby, August it must, September remember, October all over.

Step 3

Pick a place

Now you know the who and the when, it’s time to choose the where. Your dates will obviously inform this decision – perhaps you want to go somewhere with a big regatta or festival on, or you’d prefer a quiet and relaxing week away from the hustle and bustle.

Think about what you’re looking for from a Caribbean yacht charter holiday – chic European towns, rich history or an abundance of sun-drenched, palm-fringed beaches?

Young family? Best to go somewhere with lots to keep the kids entertained, like the British Virgin Islands and their abundant pirate lore. Keen sailors? Then you can’t beat the long legs in the Grenadines. Want something completely different? Belize's lush jungles and Mayan temples could be the answer. Looking for easy direct flights? Then Antigua will be ideal for you.

Step 4

What type of holiday?

Are you a group of salty sea dogs who live for the rush of gliding through the seas? Then Bareboat would be your best option.

Not a sailor but love the idea of a holiday on the water, travelling around and seeing the best of the Caribbean? A Skippered holiday would be just the ticket

If you prefer the added luxury of a private chef and host to look after your every need, then you would enjoy a Crewed yacht charter.

Sailing-to-Korcula Croatia | Helm


Ideal for experienced sailors who just want to take the ‘bare’ boat and sail themselves around the islands, in total control of where they go, when.

You’ll need a skipper’s certificate and extensive sailing experience to bareboat charter.

Helm Skipper Article 9


The answer for anyone looking to kick back and relax. A professional captain takes care of the navigation and sailing, leaving you to get as involved as you like.

But more than this – they’ll also act as your expert local guide, showing you all the hidden gems in your chosen sailing area.

Crewed 5800 Table Setting


A real step up, crewed yacht charters are the best way to experience luxury on the water.

Your professional crew will take care of the boat handling, shopping, cooking, cleaning and be on hand to look after your every need.

A holiday to leave you wanting for nothing

Step 5

Choose your Vessel

Now you have a better idea of your group, dates, and destination, it’s time to choose your yacht. You’ll need to decide between a monohull or a catamaran.

Monohull - The purists’ sailing yacht. As the name indicates, a monohull has a single hull. Good for sailing upwind, and doesn’t require much space in crowded harbours.

Catamaran - The ultimate yacht charter holiday platform. Catamarans are perfect for non-sailors, as they provide a stable and safe place, where everything is always on an even keel.

The sheer amount of space they offer makes them very attractive, especially in the Caribbean, where you’re mostly on mooring buoys, and there aren’t many harbours or tight spaces. Sail and power models available.

Peter Simon Shadow

Step 6

Ask the pros

This is what we’re here for, to help you sort the best from the rest. All of our expert brokers have spent considerable time in the Caribbean, both professionally and on holiday, so are well placed to advise you on the best places to go and things to see and do. We love planning itineraries, so get in touch if you’d like any help figuring out your route.

We’re always looking to improve our networks, and make regular trips to inspect the fleets and meet the providers we work with. This helps us be extraordinarily picky about your holiday. We’ll only ever work with the best, the yachts and companies we know and trust.

We use all of our yachting knowledge to tailor every package to fit your group and requirements, so that you get the absolute most from your holiday.

Enquire today to start building your ideal Caribbean yacht charter holiday

Create your Caribbean Yacht Charter

This site uses cookies. By continuing to browse online, you are agreeing to our use of cookies