When is the best time to sail the Caribbean

March 06, 2024 5 min

If you’re looking to book a yacht charter with us soon, one of the first questions you’ll likely ask is: “When is the best time to sail the Caribbean?”.

In short, the best time for a stunning sailing charter in this part of the world is between the months of November to May. However, this isn’t the only time suitable for a sailing vacation to the Caribbean, and we’ll explain why in this guide.

Whether you’re dreaming of an island hopping adventure in the BVI or a relaxing sailing vacation in St Thomas, we’ll be here to help you to find the best time to sail based on your preferences so you can get the most out of your trip.

When planning your Caribbean sailing adventure, it’s important to consider not just the season, but also how wind patterns and the geography of the islands shape your route. The best time to sail might depend on your sailing experience, as different regions of the Caribbean offer varying challenges throughout the year.

Best Time to Sail the Caribbean for Beginners

For beginners, the best time to sail the Caribbean is during the dry season (November to April). The northern Caribbean is the perfect place to start out, especially in regions like the British Virgin Islands (BVI) where the trade winds are steady but gentle, typically blowing between 15-20 knots.

Why this is the best time:

The dry season offers clear skies, calm seas, and more predictable weather, making it easier for those new to sailing to navigate and enjoy short, comfortable island hops. The BVI is especially suited for beginner sailors, thanks to its well-sheltered anchorages and shorter distances between islands. Sailing from island to island during this period is both easy and enjoyable, with minimal risk of sudden storms or challenging winds.

If you’re sailing outside of the peak season, the early part of the wet season (May-July) can also be a good time for beginners to explore the northern Caribbean. The winds remain fairly consistent, and while you may encounter some rainfall, the crowds are fewer, and the prices are lower.

Best Time to Sail the Caribbean for Advanced Sailors

For experienced sailors, head to the more challenging Windward Islands and southern Caribbean during the dry season (November to April). For a more exhilarating adventure, focus on later in the season between March to May. During these months, the winds pick up slightly, averaging between 20-25 knots, which creates thrilling, more challenging conditions for seasoned sailors.

Why this is the best time:

The stronger trade winds during this period allow for exciting passages, especially when sailing southward from St. Lucia through the Grenadines and towards Grenada. The dry season ensures that, despite the stronger winds, you’ll enjoy sunny days and steady conditions without the unpredictability of the hurricane season. This time of year also coincides with major regattas, like Antigua Sailing Week, giving advanced sailors the opportunity to test their skills alongside the world’s best.

The late wet season (June-August) can also be appealing, though more suited to those comfortable with variable weather. The winds are still strong, but there’s an added challenge with occasional rain showers and the potential for larger swells, particularly along the Atlantic-facing coasts.

When is the Peak Dry Season in The Caribbean?

The Caribbean’s peak season between November to April is often considered the best time for sailing, especially for those looking for near-perfect weather and pristine sailing conditions. This period coincides with the region’s dry season, characterized by calm seas, lower humidity, and plenty of sunshine.

Weather Perks: Expect average daytime temperatures between 77-82°F and pleasant breezes that make for smooth sailing. The risk of storms is at its lowest, making it the perfect season for hassle-free, tranquil voyages.

Festivals & Events: Besides the fantastic sailing conditions, peak season is also prime time for exciting events and local festivals. In November, you can experience the Cooper Island Rum Festival in the BVI, where you’ll sample world-class Caribbean rums in a breathtaking setting. April brings the Annual Seafood Festival in Antigua, a gastronomic paradise for seafood lovers.

However, be prepared for higher travel and accommodation costs during this time. Due to the influx of travelers, everything from mooring fees to flights can be more expensive, especially during the holiday period. That said, for many, the premium prices are well worth the experience.

When is the Off-Peak Wet Season in The Caribbean?

From May to October, the wet season brings increased humidity and rain. While you’ll still have plenty of sunny days, there will be more showers, particularly in the afternoons. However, if you’re an adventurous sailor or a wildlife enthusiast, the wet season has its charms too. June through November is turtle nesting season, offering the chance to witness one of nature’s most extraordinary spectacles on many islands, including St. Lucia.

If you’re flexible with your travel dates, the wet season, particularly May through early July, offers a more economical way to experience the Caribbean. During this time, you’ll find significantly lower prices on charters, flights, and mooring fees.

The Caribbean’s hurricane season runs from July to October, with September and October being the riskiest months. If you decide to sail during this time, you’ll need to keep a close eye on weather forecasts and plan flexible itineraries. Some sailors actually relish the quiet during hurricane season, as the waters are less crowded, but it’s essential to weigh up the risks.

Best Time to Sail The Caribbean to Balance Cost and Weather

The sweet spot for balancing cost and weather is often found in the shoulder months, late April and early May, when the dry season is winding down, but the heavy rains haven’t yet started. You’ll still enjoy great sailing weather with far fewer crowds and better deals.

Moreover, if you’re planning your trip outside of popular wedding seasons (May to September), you’ll avoid the influx of honeymooners, which can also drive up costs in hotspots like St. Lucia or the Grenadines.

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 of year to sail the Caribbean, you also need to factor in personal preferences.

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

To help you decide when to visit the Caribbean, you will want to consider:

Who you’re visiting with. The best time of year to go to the Caribbean may differ depending on who you’re traveling with. For a family charter aboard one of our world-class monohulls, you might choose to wait until school summer vacation for a good block of time.
What you want to do on your trip. 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-May. An Antigua yacht charter would be perfect around the Antigua Sailing Week in late April or early May. And The BVI Spring Regatta takes place in early April if you’re planning to sail then.

If you have any questions about the best time to set sail around 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.