When is the Best Time to Sail the Caribbean?

08.04.2021 Fiona Mokry

Read our expert advice on the best time of year to visit the Caribbean in a luxury yacht. Abundant sunshine, turquoise waters, year-round warm temperatures, and ideal sailing conditions make the Caribbean a top choice for a sailing holiday. From the southern tip of Florida to South America, the Caribbean’s thousands of islands provide a surplus of destinations each with unique culture, experiences, and appeals.

Best time of year to visit the Caribbean

The best time of year to visit the Caribbean is widely considered to be December to April. These months have the driest weather and moderate temperatures (averaging between 25 – 30°C). This is the most popular time to travel to the Caribbean and people flock to the region for a dose of winter sun.

The Caribbean’s low season of May to October is popular among Sailors. The weather tends to be humid during this time and the chances of rain is greater, but you’ll still enjoy plenty of sun and hot temperatures. This is a great time to visit if you are interested in certain natural and cultural occurrences such as turtle nesting season and local festivals. During May to October there are fewer tourists and more affordable prices. So depending on travel preferences it may be an even more ideal time to visit the Caribbean.

While low season can be divine, those embarking on a yachting holiday should be aware of the hurricane season.

Hurricane season in the Caribbean is from July - November. The peak hurricane months are September and October. The islands within the hurricane belt, mainly Northern islands such as the Bahamas, Cuba, and Turks and Caicos are the most affected destinations. While those that lay on the cusp or South of the hurricane belt are more likely to be passed by.

Information specific to each islands’ hurricane season can be found below. 

Md 800 voyage 500 yacht turquoise caribbean water

Best time to visit Bahamas

The Bahamas encompasses 700 islands, only 30 of which are inhabited. One of the major perks of a yacht charter in the Bahamas is the ease of finding your own slice of Caribbean heaven. Whether you choose to visit the popular Bimini or Exuma islands, or break free from other sailors and head to the uninhabited, more remote (and aptly named) Out Islands, the Bahamas has something to offer sailors of every experience level.

The best time of year to go to the Bahamas is December to April. This is the time when temperatures are just right, rain is infrequent, and winds are ideal. The shoulder months of May and November are also good because they still offer great weather and fewer sailors.

While hurricane season exists in the Bahamas, history shows us that hurricanes often veer north and the island avoids a direct hit. If your boat holiday falls within the hurricane season of July to November, the Bahamas may be a good choice.

November Shoulder month - great weather, less sailors
December to April Best time of year - Dry, perfect winds, good temperatures
May Shoulder month - great weather, less sailors
July to November Hurricane season



Best time to visit Turks and Caicos

Turks and Caicos is known for its tranquil vibes, and while there’s not much in the way of nightlife, there’s plenty of pristine beaches, diving and snorkelling opportunities, and stunning natural beauty.

The high season of November to April attracts the most boaters to Turks and Caicos idyllic shores. Beautiful weather is likely all year round, making the islands a dreamland for a yacht charter holiday.

Our favourite months to visit Turks and Caicos are April or May, the cusp of the low season. At this time you can expect perpetual sunny skies and average temperatures around 25-26°C, making them advisable months for a visit. 

Hurricanes are possible on Turks & Caicos but the islands aren’t as commonly hit as other Caribbean destinations. On average, Turks & Caicos is hit by a hurricane once every seven years. August and September bring the highest risk of hurricanes, but they are relatively rare overall. If you’re willing to be flexible with your boating holiday, you’ll be rewarded with far fewer visitors and very reasonable prices on the islands if you travel in July to October.

November to April High season
April and May Very sunny, 25-26°C
July to October Fewer visitors and reasonable prices
August and September Possible hurricanes



Best time to visit St Barts

Blending laidback island vibes with an air of French sophistication, St Barts is an exclusive destination for your next yacht charter. Spend your days on one of the islands fourteen beaches, or head to dry land for shopping and nightlife. Regardless of your preferences, St. Barts delivers on all fronts.

St. Barts’ high season starts in December and runs through April, with December considered as the peak month. But high season doesn’t necessarily mean the best season.

April to June is also an excellent time for a St. Barts holiday. Daily highs of 30°C and daily lows of around 25°C make for more comfortable sleeping weather.

The fall season is considered more prone to storms. September is the month that is most likely to bring a hurricane, although the risk is low. Historically speaking, it’s unlikely for St. Barts to be severely impacted by a hurricane more than twice in 10 years, which stacks the odds in your favour. While the island sees more rain in September, October, and November, these months are a quiet time to plan a visit and see what local life is really like.

December to April St Barts High season
December Peak month
April to June 25-30°C, comfortable for sleeping
September Possible hurricanes
September to November More rain, quieter, experience local life



Best time to visit the British Virgin Islands

This volcanic archipelago of over 60 islands is the stuff of sailors’ dreams. With premiere dive sites, pristine national parks (both above the water’s surface and below), world-class beaches, and island-hopping opportunities galore, BVI is a top Caribbean destination for a yacht vacation. And don’t forget to come ashore to hit up one of Jost Van Dyke’s famous beach bars.

High season in the British Virgin Islands is December to April. These are excellent sailing months with steady wind and lively boating scene. The low season months of May, June, and November are also good times to set sail around BVI if you prefer a little more seclusion. 

July-October marks the low season and brings more rain. While rain showers can be sudden and sometimes intense, the sunshine is strong and plentiful year-round.

The British Virgin Islands are located in the more storm-prone hurricane belt, and although rare, the greatest probability of a hurricane striking the islands is between August and October. If you plan to travel then, you’ll still experience 29°C temperatures and lots of sun interrupted by tropical rain.

December to April High season
May, June and November Low season, good time to visit BVI
August to October Possible hurricanes, 29°C, lots of sun, some tropical rain



Best time to visit US Virgin Islands

Directly south of BVI, the U.S. Virgin Islands are composed of three gems: St. Thomas, St. Croix, and St. John. The tip of BVI is less than 20 kilometers off the northern coast of St John, tempting sailors with an irresistible multi-country yacht excursion.

December to March is peak season in the U.S. Virgin Islands with temperatures ranging between 23 – 30°C and ideal sailing winds.

April to June still claims an ideal climate for a yacht vacation with mild temperatures and very little rainfall. This is also the best time to catch Leatherback turtles laying their eggs on St Croix!

Similar to BVI, the U.S. Virgin Islands are located along the hurricane belt. On average, a major hurricane makes landfall on the islands about once every 8 years, while one will pass close by once every 3 years. September and October are the months when this is most likely to happen, however the hurricane season does run from June to October.

December to March Peak season, 23-30°C, ideal sailing winds
April to June Ideal for yachting. Mild with little rainfall
June to October Hurricane season
September and October Most risk of hurricanes



Best time to visit Colombia

You don’t have to island hop to get a taste of the Caribbean. There are plenty of mainland destinations lining the tropical sea that offer prime sailing opportunities, rich cultural experiences, and relaxing holiday vibes. A yacht charter in Colombia provides the chance to explore the northern tip of the country while still enjoying all the perks of the tropics. The port city of Cartagena is a welcoming harbor and gives sailors a chance to trade their sea legs for dry land. Visitors shouldn’t miss exploring the Old City Walls, visiting several noteworthy museums, and hiking the 500-foot hill to Convento La Popa de la Galera.

The best time to visit Cartagena is the summer season of December to April. Temperatures in Colombia stay around 28°C year-round, but the summer season sees less rainfall, making these months the ideal time to visit.

May to November ushers in the rainy season, however June and August receive less than the other months on average. If you want to take advantage of the outdoor attractions and beaches, it might be wise to steer clear of Cartagena in October and November.

December to April Best time to visit Colombia, 28°C, less rainfall
May to November Rainy season, 28°C



Best time to visit Belize

Belize’s dry season is from November through mid-April. This is considered the best time to visit the country and draws the biggest crowds. If crowds aren’t for you but prime weather is key, a Belizean yacht charter gives you the freedom to leave the people behind and explore Belize’s Barrier Reef and the hundreds of uninhabited islands off the coast.

If fewer tourists are more important than constantly clear skies, plan a visit between May and June. Your reward? Thinner crowds and comfortable temperatures with only a moderate increase in humidity. Showers pass through in the afternoons and overnight, but it won’t put a big damper in your plans. 

A yacht holiday in Belize feels enjoyable most of the year due to the pleasant climate and agreeable sailing conditions, however get ready to don a poncho if you visit in August to October. These are also the months when a hurricane is mostly likely to strike the coastal country. Perks of visiting Belize at this time include partaking in two of the country’s biggest annual celebrations - La Costa Mayan International and Independence Day - which can be a unique way to experience a new country. This is also a great time to discover Belize if lower prices are important to you.

November to Mid-April Dry season, best time to visit Belize, but biggest crowds
May and June Less crowded, comfortable temperatures, some brief showers
August to October Rainy season, possible hurricanes, International Costa Maya Festival, Independence Day



Best time of year to visit Cuba

December to May presents prime sailing conditions and warm temperatures of 26°C on average around Cuba.

If you don’t mind rainy spells, higher temperatures, and humidity, June to August and November are also good months to embark on a Cuban yacht charter adventure.

September and October bring the highest risk for hurricanes; however, it is very possible to travel to Cuba in these months and experience sunshine and dry weather. On average, hurricanes hit Cuba once every four years. There’s definitely appeal to visiting Cuba in low season.

If you love a good party, Cuba’s Revolution Day in July offers a peek into local traditions and a month-long festive atmosphere.

December to May Best time for sailing, warm temperatures average 26°C
June to August, November Good time to visit. Higher temperatures, humidity, rainy spells
September and October Possible hurricanes
July Revolution Day, local traditions and festive atmosphere


The islands of the Caribbean all possess tropical waters, ideal sailing conditions, and plenty of warm sunshine, and endless opportunities for avid sailors. The eclectic mix of culture and unique experiences each island offers is what makes a yacht holiday in the Caribbean special.

Which island will you choose for your next holiday?