The Best Times to Visit the Caribbean on a Sailing Holiday


The Caribbean is a land of dreams for most people. It conjures up images of azure blue oceans and sun dappled beaches like a vision of heaven on earth. 

However, it is important to remember that it is not a single country, but a region made up of coasts and islands in the Caribbean Sea.

That is why it is one of the popular choices for a sailing holiday. The ability to cruise between different parts of the region at your own pace will ensure a memorable Caribbean break.

There are good and bad times to take such a trip there though, so let’s look at what you need to know about planning a sailing holiday in the Caribbean.

Why Sailing is the Best Bet

A sailing trip in a specially chartered vessel isn’t the only Caribbean vacation available, but it is the one that you should choose. The fact that the Caribbean is made up of several islands makes sailing preferable to a land-based holiday, because it will let you visit more of them.

As beautiful and fascinating as Puerto Rico and Jamaica undoubtedly are, why spend your entire holiday tied to one part of the region when you can explore it all with your own personal boat? Of course it means choosing a vessel and booking it, but that does not need to be a complicated matter in 2022.

There are a few things that you will have to decide on before you actually charter a boat though.

The Type You Want

The two main types of boat that people typically sail to the Caribbean are yachts and catamarans. The latter is the vessel that most people choose, as it offers a couple of pretty important advantages.

  • More space

Being twin hull vessels, catamarans are usually wider than yachts and that means they can provide greater cabin and deck space. That makes them more luxurious for a holiday, while the bigger ports – or windows – are better for savoring those divine Caribbean ocean views.

  • Greater stability

Catamarans provide a greater degree of stability on the water than yachts. That will help to make sure that your trip is not ruined by seasickness.

Of course, everyone is not the same and some people do prefer a yacht. As these are smaller, they are usually a bit less expensive to hire and to berth.

The best way to check out different prices for a BVI’s yacht charter is to book online using a company like Borrow a boat. They will provide both bareboat and crewed charters, with many other aspects that would benefit your experience. 

You should only choose bareboat if you are a confident sailor. If this is going to be your first sailing holiday, having a small professional crew with you will be much safer and catamarans are sizeable enough to guarantee your privacy even with them on board.

Really difficult conditions are less likely to be encountered if you visit the Caribbean during the peak sailing months, but it is better to err on the side of safety.

The Best Times to Sail to the Caribbean

With every sailing holiday destination there are good and bad times to visit. It largely comes to down to the weather and conditions on the ocean at different times of the year.

December to April – the Dry Season

This is the most sensible time of the year to take a sailing holiday in the Caribbean. It is known as the region’s ‘dry season’ because rainfall is much lower and it also offers sunshine without the extreme humidity of summer.

However the main reason it is the peak sailing period is that the waters of the Caribbean Sea are at their calmest. That will guarantee a smooth trip.


The excellent weather between December and April means that there will be lots activities available to you.

  • Scuba diving or snorkeling

You need a calm ocean for snorkeling or scuba diving to be safe and fun. The Caribbean waters can bring you into close contact with colorful tropical fish, coral reefs and even the odd shark!

If it is those scary creatures you want to see, the Bahamas will provide the best opportunity. On the other hand, Dominica and Silver Bank, off the coast of the Dominican Republic, will allow you to swim amid humpback and sperm whales.

  • Sunbathing

The ideal spots for sunbathing during the dry season are the islands in the south. That means places like Curacao and Aruba.

The beaches in northern parts like the Bahamas will be too cool for most tastes.

  • Nightlife

The dry season is party time across the Caribbean. You can come ashore to experience Carnival Season throughout February or the Saint Lucia Jazz and Arts Festival in April.

  • Water sports

The gentle waters on offer during the December to April stretch make it perfect for oceanic sports like waterskiing. 

When Not to Go

June to November – The Rainy Season

This period of the year sees the Caribbean hit with much more frequent and heavier rain. It is also known for extreme heat, hurricanes and tropical storms.

That makes it a dangerous time to sail. If you want to take advantage of the lower prices during the rainy season, avoid a boating trip.

Now you know how and when to take a Caribbean sailing trip, all you need to do is book.


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