When is the best time of year to sail the Caribbean?

17 December 2024 4 min

The best time to go to the Caribbean on a stunning sailing charter is between November-May.

We understand that planning a holiday can seem overwhelming and stressful which is why, at The Moorings, we are dedicated to supporting you every step of the way, from deciding which destination to set sail around all the way to choosing whether you want a bareboat, skippered or crewed charter. You deserve to feel relaxed and feel your troubles melt away before you even step foot on one of our state-of-the-art power yachts.

One of the key considerations when planning a sailing holiday is deciding the time of year you want to feel the wind in your hair and sun on your face. Whether you’re dreaming of an idyllic yacht charter in the BVI or a relaxing sailing holiday in St Thomas, you might be wondering, when is the best time to sail the Caribbean?

In this blog, we’re doing a deep dive into when to visit the Caribbean, looking at weather, season and cost. Before you know it, you’ll be sunbathing on powder-white sands and sipping rum cocktails. Let’s get started…

When to visit the Caribbean: Dry Season vs Hurricane Season

The Caribbean is unique in that it offers exceptional year-round sailing conditions, although it has three seasons that you need to be aware of when planning your dream yacht charter and deciding when to visit the Caribbean:

Dry Season – The dry season in the Caribbean is also known as the peak season due to its brilliant sailing conditions, sizzling weather and popularity. One of the best times to visit the Caribbean, is the dry season runs from November to April. During this time, you’ll also have the unique opportunity to celebrate cultural events and attend fantastic festivals, such as Cooper Island Rum Festival in the BVI which takes place in November and the Annual Seafood Festival in Antigua which happens in April.
Wet Season – The Caribbean’s wet season takes place between May and October. If you book a sailing charter during this time, you’ll experience warmer temperatures but, as the name suggests, more rainfall. If you’re an animal lover, you might decide this is the best time to sail the Caribbean as November also marks turtle nesting season so you may have the opportunity to come face to face with these majestic creatures.
Hurricane Season – Nestled within the wet season is the Caribbean’s hurricane season which falls between July-October. September and October are generally considered the peak months for hurricanes so you need to take this into consideration when planning your blissful yacht charter.

Each individual island may differ slightly when it comes to weather conditions, including rainfall, sunshine and temperatures, although one thing is for certain…the Caribbean is the perfect winter sun destination. Swap frosty mornings, snow-covered roads and dark nights for golden beaches, turquoise waters and breathtaking island views.

Best time to sail the Caribbean for cost

While the dry season is considered the best time to sail around the Caribbean, when it comes to sailing conditions and weather you might also be wondering, when is the best time to visit the Caribbean in terms of cost?

The most popular time of year to visit the Caribbean is during the peak season (November-May) which means you can expect to pay higher mooring fees and travel costs. In particular, the Christmas period can be a particularly expensive time to sail the Caribbean.

The wet and hurricane seasons often attract fewer crowds and, as a result, it may cost less to book your exciting yacht charter during this time.

Also, many of the picturesque Caribbean islands, such as St Lucia, are popular honeymoon destinations. With wedding season running from May to September, booking your peaceful sailing holiday outside of this time may result in lower costs. Dreaming of your perfect honeymoon? Take a look at our top romantic sailing destinations and read our blog on honeymooning in the BVI.

It’s important to note, however, that while costs may be lower in the wet and hurricane seasons, there is a much higher potential for rain and storms so you need to consider very carefully whether you want to set sail during the low season. Get in touch and speak to one of our Holiday Planners who can provide further insight.

Tips for choosing the best time of year to sail the Caribbean

While weather, season and cost are very important, when considering the best time to go to the Caribbean, you also need to factor in personal preferences.

When you book a sensational Caribbean sailing holiday with The Moorings, you have the freedom to design your ideal holiday, from the type of charter to the catamaran model and itinerary.

Picture yourself soaking up the sun as you swim in the crystal clear waters of the Caribbean Sea. Imagine yourself exploring uninhabited islands, admiring their natural beauty. To help you decide when to visit the Caribbean, ask yourself the following questions:

Who are you visiting with? The best time of year to go to the Caribbean may differ depending on who you’re travelling with. For example, if you’re embarking on an exhilarating family charter aboard one of our world-class monohulls, you might choose to wait until the School Summer holidays.
What will your itinerary look like? If you want a fiercely fun sailing charter filled with races and regattas, you’ll want to book during the peak racing season which runs from November to May. If you’re booking an Antigua yacht charter, you’ll love Antigua Sailing Week between 27 April-3 May. Setting sail around the BVI? The BVI Spring Regatta takes place between 1 April-7 April.

Whether this is your first or tenth time sailing around the Caribbean, you can rest assured we will support you every step of the way, including pre-charter briefings and our experienced base staff.

As well as caring for you, we also care deeply about protecting the environment and preserving the stunning destinations we have bases in. Learn more about our sustainable travel commitment so that you can set sail around the Caribbean responsibly.

If you have any questions about the best time to sail in the Caribbean, including the BVI, Antigua and St Lucia, please get in touch with us today and a member of our team will be happy to answer.

What are you waiting for? Choose one of our Caribbean destinations, build a quote and book your dream yacht charter today.