Weather & Passage Planning for Sailors in the Caribbean

In a Nutshell...

For sailors in the Caribbean, Caribbean weather for sailors is defined by the consistent trade winds, the occasional but manageable squall, and the distinct hurricane season. Successful passage planning relies on understanding these patterns, staying alert to local conditions, and always having a plan B. The key is to be prepared, not scared.

Beneteau 473 under full sail in perfect sailing conditions, somewhere in the Caribbean

Perfect sailing conditions, but it's not always like this in the Caribbean

What's the best time of year to sail the Caribbean?
What are the prevailing winds & how do they affect sailing?
Getting to grips with local weather patterns
Northerly Swells
How do you handle squalls & heavy weather?
How do you create a safe passage plan?
Navigation & Technology
Emergency Procedures
What are the effects of the hurricane season?
A Guide to Hurricane Season Preparation
Summing Up
Frequently Asked Questions

When's the best time of year to sail the Caribbean?

The Caribbean sailing season is typically split into two main chunks: the high season and the low season. The high season, from roughly mid-December to April, is when the weather is at its most stable and pleasant. During this period, the North East Trade Winds are pretty reliable, often blowing between 15 and 25 knots. This makes for exhilarating sailing conditions with long, steady swells. The air is less humid, and while you'll still see rain, it's usually in the form of short, intense squalls that blow through quickly. This is also the period for the 'Christmas Winds', which can really kick up to 30 knots or more, so be ready to reef.

The low season, from June to November, is the official hurricane season. While this might sound daunting, it's important to remember that hurricanes are infrequent and highly predictable, unlike a sudden squall. Early in the season (June and July) and late in the season (November), the weather is often fantastic, with lighter winds and calmer seas. Many experienced sailors find this a cracking time to cruise, enjoying the quieter anchorages and often better prices. But you've got to be vigilant and have an escape plan, which often means heading south to islands like Trinidad and Tobago, or Grenada, which are considered to be below the main hurricane belt.

What are the prevailing winds & how do they affect sailing?

The prevailing winds throughout the Eastern Caribbean are the North East Trade Winds. As a rule, they're your best mate, offering a steady, reliable source of propulsion for your boat. For a sailor, this means you can plan your passages with a high degree of confidence, knowing you'll have wind on the beam or a little aft of it as you island-hop down the chain from north to south.

However, these winds aren't without their quirks. From personal experience, I can tell you that they do occasionally swing around to the southeast, particularly in the summer months. This can make a planned passage feel quite different, sometimes necessitating a bit more motoring or a change of tack to keep the sails drawing properly. The key is to be flexible and have a good weather forecast.

Another significant effect of these winds is the acceleration zones found at the ends of islands. As an air mass hits the land, it's compressed and forced around the headlands, causing the wind speed to increase dramatically. The northern end of St Vincent is a classic example. I've sailed down the lee side in a gentle 15-knot breeze only to round the corner and be hit by a solid 25-knot gust, with the accompanying short, steep seas. It's a jolt to the senses and a reminder that local knowledge and careful passage planning are crucial.

Getting to grips with local weather patterns

While the trade winds are the dominant force, local conditions can have a huge impact on your daily sailing. The most common phenomenon is the daily thermal breeze. During the day, as the land heats up faster than the sea, warm air rises over the islands and cooler, denser air from the ocean is drawn in. This creates a predictable sea breeze that blows onto the shore from around 10 a.m. to 4 p.m. In the evening, the reverse happens: the land cools faster than the sea, causing a land breeze to blow from the island out to sea. This is why many anchorages become calm in the evenings, offering a peaceful night's sleep.

For a sailor, this means that an early morning departure from an anchorage can often be calm and easy, but a late afternoon arrival might require a bit more motoring into a building sea breeze. Reading the clouds is also a crucial skill. A well-developed line of cumulus clouds over a particular island can indicate an acceleration zone or a squall line forming over the landmass. Learning to interpret these visual cues is just as important as checking a weather app.

Northerly Swells

The Caribbean is generally known for its gentle, long Atlantic swells, but there's a specific, seasonal threat that can catch you off guard: northerly swells. These aren't generated by local winds but are the result of powerful winter storms that form far up in the North Atlantic. These storms can create massive wave trains that travel thousands of miles and arrive, seemingly out of nowhere, at the northern shores of the Caribbean islands.

When they arrive, what was once a calm, serene anchorage can become a wild, uncomfortable, or even dangerous place to be. The northerly swells can wrap around the northern tips of islands, making anchorages on the leeward (west) side of the island untenable. I've had to pull anchor and find a new spot more than once because a beautiful bay had become a rolling mess overnight. Always check the long-range swell forecast during the winter months, and be prepared to move if heavy northerly swells are on the way.

How do you handle squalls & heavy weather?

Squalls are a fact of life in the Caribbean. They're typically localised, intense rain and wind events that can blow up in a matter of minutes. The tell-tale sign is a menacing, dark cloud on the horizon. The trick is to spot them early. You'll often see a visible line on the water, marking the leading edge of the wind.

When you see one coming, your first action should be to assess its trajectory. Is it going to pass ahead of you, or are you in its path? If it's going to hit you, don't wait. Prepare for the worst-case scenario. This means:

Reduce sail: Reef your mainsail and perhaps roll up the genoa entirely. It's far better to be a bit under-canvassed for a few minutes than to be overpowered and out of control.

Secure everything on deck: A sudden gust can send loose items flying.

Close all hatches: The rain that accompanies a squall is often torrential and can flood a cabin in seconds.

Wear appropriate foul-weather gear: Even in the tropics, a sudden dousing from a squall can be chilling.

Once the squall hits, it's a bit like being in a washing machine for a few minutes. You'll likely experience a sudden increase in wind, sometimes up to 40 knots or more, and a near-total loss of visibility due to the driving rain. It can be unnerving, but they are almost always short-lived. The wind will ease, the rain will stop, and the sun will often reappear as if nothing ever happened.

An approaching squall, although you might miss the worst of ir.

If you haven't reefed your sails, now would be the time...

How do you create a safe passage plan?

A well-thought-out passage plan is the cornerstone of safe sailing in the Caribbean. It's not just about drawing a line on a chart; it's about anticipating conditions, understanding the quirks of the local geography, and being ready to adapt. Here's my process, honed over many years of sailing in these waters:

Consult multiple weather sources: Don't rely on a single app. Use a combination of forecasts from sources like PredictWind, Windy, and local weather reports. Look at the general wind direction and strength, but also pay attention to any mention of squall activity.

Factor in wind & sea conditions: Consider how the prevailing wind will affect your chosen course. If you're sailing upwind, are you prepared for a bumpy ride? Downwind, are you ready for the large swells? My experience is that sailing between islands is where you truly appreciate the long, Atlantic swells. They're magnificent and rarely uncomfortable.

Plan your departure & arrival times: Aim to get to your destination in good daylight. Anchoring for the first time in a new bay is challenging enough without doing it in the dark.

Consider "plan B" anchorages: Always have an alternative in mind. The ideal anchorage might be full, or the wind direction might have shifted, making it untenable. Knowing a few other options along your route can save a lot of stress.

Review the charts for local hazards: Pay attention to any reefs or shoals. While most charts are excellent, a quick look at satellite imagery on apps like Navionics can give you a better visual sense of an anchorage's layout.

Navigation & Technology

Modern technology has transformed passage planning, but it's a supplement, not a replacement, for traditional seamanship. While paper charts should always be on board, apps like Navionics and Savvy Navvy offer invaluable real-time data. Navionics, with its community-sourced SonarChart feature, can show highly detailed bathymetry (water depth) that can be a lifesaver when navigating tricky anchorages or reefs. Savvy Navvy, on the other hand, is great for its intuitive route planning, which automatically factors in wind and current data to plot the most efficient course.

Beyond chart plotters, a reliable AIS (Automatic Identification System) is a must for collision avoidance, especially when crossing shipping lanes or in crowded anchorages. It allows you to see other vessels’ courses, speeds, and names on your screen. When in areas without mobile service, a satellite communication device like an Iridium GO! or a Garmin inReach is critical for receiving up-to-date weather forecasts and for emergency communication.

Emergency Procedures

Being caught in an unexpected weather event is a test of preparation. The most common emergency for a Caribbean sailor is getting caught in a severe squall. While the article discusses what to do before one hits, a good emergency plan also covers what to do if you are caught out.

Heave-to: If the wind becomes too strong to sail or motor comfortably, heaving-to is an excellent way to slow the boat down and manage the conditions. This involves backing the headsail and setting the rudder to create a balanced helm, allowing the boat to ride out the worst of the weather with minimal input.

Emergency Anchoring: If you are near a lee shore or have a sudden engine failure in high winds, knowing how to execute an emergency anchoring procedure can save your vessel. Ensure your anchor and rode are always flaked and ready to be deployed.

Running Under Bare Poles: In extreme conditions, even a deeply reefed mainsail can be too much. In such a case, dousing all sails and simply steering the boat under bare poles—without any sail up—can be the safest option, allowing you to ride with the wind and waves in a more controlled manner.

Emergency Equipment: Ensure your grab bag is easily accessible and contains essential items like a handheld VHF radio, flares, a first-aid kit, and an EPIRB (Emergency Position Indicating Radio Beacon). Every crew member should know its location and contents.

Sailing the Caribbean is a fantastic experience, but it’s always wise to be prepared. For more in-depth information on all aspects of cruising the region, from customs to provisioning and local knowledge, our comprehensive article on Sailing in the Caribbean: Information for Skippers & Crew is an invaluable resource.

What are the effects of the hurricane season?

The Atlantic hurricane season runs from 1st June to 30th November. While it's a very real threat, it's also a highly monitored one. Unlike a squall, a hurricane doesn't just pop up unexpectedly. They form over days, sometimes weeks, giving you ample time to prepare and get out of the way.

Many experienced skippers take advantage of the much less crowded anchorages and are happy to continue cruising during the hurricane season. The strategy is simple: vigilance and a plan. The US National Hurricane Center (NHC) provides excellent, up-to-the-minute information on tropical depressions, storms, and hurricanes. You should be checking their updates daily.

If a storm is heading your way, your options are:

Move south: The further south you go, the less likely you are to be affected. Grenada, Trinidad & Tobago, and the ABC islands (Aruba, Bonaire & Curaçao) are all considered to be outside the main hurricane belt.

Find a hurricane hole: These are well-protected anchorages or marinas designed to offer maximum protection from strong winds and storm surges.

Haul out: The safest option is to have your yacht hauled out of the water and secured on land. Marinas in the southern Caribbean are well-equipped for this.

The bottom line is that while the threat is real, a proactive approach and a solid plan makes it a manageable risk for any sailor.

Antigua, English Harbour mangroves. A well-known hurricane hole

The mangroves in English Harbour, a well-known hurricane hole, in clement conditions.

A Guide to Hurricane Season Preparation

Action	Description	Why it's important
Monitor Forecasts	Regularly check weather updates from the NHC and other reliable sources.	Early detection provides maximum time to execute your plan.
Have an Escape Plan	Identify a route to a safe zone, such as south of the hurricane belt.	Having a pre-planned route minimises panic and wasted time.
Prepare the Vessel	Remove all sails, biminis, & anything on deck that can be blown away.	Reduces windage and prevents costly damage to your boat.
Secure the Rigging	Ensure all shrouds and stays are properly tensioned.	A well-secured mast is less likely to suffer damage in high winds.
Arrange for Haul Out	Book a haul-out at a reputable marina well in advance.	This is the safest option & peace of mind is invaluable.

Summing Up

Successful sailing in the Caribbean hinges on respecting the elements and planning ahead. The consistent trade winds make for fantastic sailing, while the occasional squalls and the more serious threat of hurricanes demand a prepared and vigilant skipper. By understanding the local weather patterns, using multiple resources, and always having a "Plan B," you can ensure your Caribbean cruise is a safe and memorable one.

This article was written by Dick McClary, RYA Yachtmaster and author of 'Offshore Sailing' published by the Royal Yachting Association ( RYA) and member of The Yachting Journalists Association (YJA).

Frequently Asked Questions

What's the difference between a squall and a storm?

A squall is a localised, short-duration event with a sudden increase in wind and rain. A storm is a much larger, more organised weather system, which can last for days and have far-reaching effects.

Do the trade winds blow all year round?

Yes, they do, although their strength and direction can vary. They are generally stronger and from a more northerly direction in the winter, and can be lighter and from a more southerly direction in the summer.

How do I check for heavy northerly swells?

During the winter, strong storms in the Atlantic can send heavy swells down to the Caribbean. Check swell forecasts on marine weather apps. If heavy northerly swells are forecast, be aware that many anchorages on the north coast of islands will be untenable.

What is a "hurricane hole"?

A hurricane hole is a naturally or artificially protected harbour or bay that offers shelter from high winds and storm surge during a hurricane.

How far south do I need to go to get out of the hurricane belt?

While no place is completely immune, islands like Grenada and Trinidad & Tobago are generally considered to be below the main hurricane belt and are popular choices for yachts to shelter.