Best Time to Sail the Caribbean

20 March 2024 4 min

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

The sailing season runs from November-April, which is generally considered the best time to sail the Caribbean as you’ll experience the most incredible sailing conditions and weather.

However, the Caribbean is unique in that it’s a year-around sailing destination, meaning you will enjoy an exceptional bareboat charter or skippered charter whenever you decide to visit.

So, the question remains… when should you visit the Caribbean?
The answer depends on a number of factors, including who you’re travelling with and what you plan on doing when you set sail. To help you make a decision as to when to visit the Caribbean, we have created this guide which. Covering everything from the best time of year to visit the Caribbean for families to water sports lovers and couples, you’ll be booking your dream sailing holiday in no time at all.

Best time to sail the Caribbean for families

We think the best time to sail the Caribbean as a family is during the peak season because it’s generally more popular which means more opportunities for children to socialise and make friends.

We understand that finding holiday destinations for families can be difficult, particularly if you are limited by School term time. However, this is partly what makes the Caribbean such a family-friendly option as there are several times of the year that are great for sailing.

If you decide to book a sailing charter during the peak season (November-May), the best time to go to the Caribbean would be during the Christmas or Easter holidays, both of which fall into this time. If you have young children who aren’t yet in School, any time during the peak season would ensure a blissful yacht charter.

If you want to avoid peak season costs, the best time to visit the Caribbean is during the Summer holidays, between July-September. It should be noted, however, that this is the Caribbean’s hurricane season which means you could be faced with particularly adverse weather conditions. No matter what time of year you’re setting sail, your safety is our highest priority. To learn more about how to keep safe while cruising in the Caribbean, take a look at the ‘useful information’ tab on the individual destination pages.

Whenever you decide to visit the Caribbean, we know you’ll enjoy a family holiday to remember.

When to visit the Caribbean as a couple

Whether you’re celebrating an anniversary, escaping for some winter sun, or marking your retirement, there’s no better feeling than booking a romantic couples holiday.

We understand that you might want a more intimate, private holiday outside of the high season, without compromising on the weather and sailing conditions. This is why we believe the best time to visit the Caribbean for couples is during the wet season.

The wet season runs from May-October and, while you’ll experience more rainfall and higher humidity, you’ll still enjoy fantastic temperatures, brilliant sailing conditions. If you visit between May-June, you’ll likely experience sizzling temperatures ranging from 78 to 87 degrees.

This is also considered the best time to sail the Caribbean as a couple if you’re looking for less crowds and lower costs, as expenses rise during the peak season.
If you have any questions about when to visit the Caribbean as a couple, whether you want to set sail around Grenada, Martinique or beyond, please get in touch with us today.

When is the best time to go to the Caribbean if you love water sports?

Do you love the thrill of adventure holidays? Is your itinerary always filled with swimming, snorkelling and scuba diving? You might be wondering, when is the best time of year to visit the Caribbean for water sports.

Taking into account visibility, marine life and activities, we think April is the best time of year to sail the Caribbean if you love water sports.

Why is April the best time to sail the Caribbean if you love water sports?

Many sailing races and regattas take place during April so you can immerse yourself into sailing culture and surround yourself with like-minded adventurers. Heading to Antigua? Antigua Sailing Week is April 27th-May 3rd. Booking the BVI? The BVI Spring Regatta is April 1st-April 7th.
The Caribbean is renowned for its abundant marine life and majestic reefs. You’re most likely to spot beautiful marine life between October-May which means, when you book a sailing charter in April, you may have the incredible opportunity to discover Whale Sharks in Belize, Atlantic spadefish in Antigua or Angel Fish in the BVI. Protecting and preserving marine life and their environment is incredibly important. Take a look at our sustainable travel policies and learn more about eco-friendly sailing.
April is part of the peak season in the Caribbean which means you’ll have near-perfect visibility for snorkelling, dry weather for swimming and calm waters for scuba diving.

Best time to visit the Caribbean for culture

From embracing laid-back island living to sipping on rum cocktails and enjoying exquisite Caribbean cuisine, one of the best parts of any sailing holiday in the Caribbean is immersing yourself into local culture.

While you’ll get a taste of Caribbean culture whenever you choose to climb aboard one of our yachts, there are certain times of the year where you can experience it more than others. The best time of year to visit the Caribbean for culture will depend on which of our idyllic destinations you’re visiting.

To find out the best time to sail the Caribbean from a cultural perspective, head to our individual destination pages and find out the following information:

Cultural events that take place annually, for example Christmas in July in the BVI.
Activities, attractions or excursions that may only be open at particular times of the year.
National holidays that take place annually.
Seasonal cuisine that is only available (or at its best) at certain times of the year.

All of this information will help you work out which time of year is best for setting sail if you want to capture the essence of the Caribbean.
So, what are you waiting for? Choose your dream Caribbean sailing destination and book your idyllic yacht charter today.