Are you planning to sail the Caribbean? Are you familiar with the hazards associated with sailing to the Caribbean? Have you thought which season or month would be best for sailing the Caribbean?

When To Sail The Caribbean

The Caribbean is a region that consists of the Caribbean sea, many islands, and coastal areas. The Caribbean sea is one of the most popular offshore destinations for most sailors. 

The best time to sail across the Caribbean is during the start and end of the fairly warm summer season when the weather conditions are almost stable. Thus, it is best to sail the Caribbean when there is less chance of hurricanes.

This blog will provide an insight on when it’s the best time to sail the Caribbean.

Let’s dive in.

Reasons to Sail the Caribbean:

Some people just love to explore the world and would love to explore the Caribbean as well. But what if the sailors consider sailing the Caribbean for some other reasons?

When To Sail The Caribbean

Let’s provide you with some details.

  • It is home to the most beautiful beaches in the world.
  • The water of the beaches is crystal blue in color as there are no industries and wildlife is found hovering near the beach, such as dolphins.
  • The weather is warm all year round, around 75F to 85F.
  • Strong winds blow for 15-25 knots from the east -the best time to sail considered by sailors.
  • The Caribbean covers over 20 different countries. For example, if you sail from St Lucia to Martinique (5-hour sailing distance), you’ll find yourself in a new diverse country.


People love to visit the Caribbean from all over the world, especially from Africa, Europe, and the United States. These are some of the reasons for which the sailors decide to sail the Caribbean.

Sailing Hazards in the Caribbean:

Now comes the most dangerous part of sailing in the Caribbean. 

Sailing in the Caribbean is not as easy as you think. You won’t believe that regardless of the warm weather conditions, there is a chance of hurricanes and thunderstorms.


Thunderstorms are the main characteristic of the Caribbean, and many sailors face them. The thunderstorms consist of elevated waves, rain, hail, lightning, and stormy winds. The Caribbean thunderstorms are extreme but short-lived. Plus, thunderstorms usually occur in the summer season, so it’s better to be careful when sailing around.


Hurricanes usually occur from May to October with sustained winds around 100 knots or more. They are around 100 miles wide and are more hazardous than the not-so-damaging thunderstorms.

Usually, warnings are available beforehand a hurricane development. So most people tend to avoid sailing in these months. 

Best Months to Sail the Caribbean 

The best time to sail across the Caribbean is those months that have fewer chances of thunderstorms and hurricanes.

The perfect months for sailing are:

  • May – Less chance of thunderstorms and hurricanes.
  • June – Thunderstorms are rare and fewer chances of hurricane development.
  • July – No chance of thunderstorms, but hurricanes have occurred in July.
  • August – Hurricanes, and storms are common.
  • September – The weather conditions are severe, and it’s not safe to sail this month.
  • October through November – High risk of encountering extremely severe weather conditions.



Have you made your mind up to sail the Caribbean regardless of the dangers associated with it? If you have, then, now you must be thinking about buying a sailboat. Let’s suggest the best and affordable boat dealer.

Massey Yacht is one of the best boat providers. They have a variety of unique designs, and you should surely check out what we have to offer.

Feel free to contact us if you have queries and concerns.