Sailing to explore the islands of the Caribbean can be quite an adventure. The diverse cultures found on the islands can provide an educational, cultural, and culinary experience for those visiting. If it is your desire to island hop in the Caribbean, then it is important to know when is the best time to sail in the Caribbean.


The Best Time to Sail

The months from February to June is the best time to sail in the Caribbean waters. This time of year is known as the dry season, but don’t be surprised by a rain shower popping up occasionally.

During this time of year, one can expect the temperature ranging from the mid-70s to mid-80s, allowing comfortable weather to sunbathe, shop, or play on the island beaches.

Depending on the island you choose to dock, during the end of February and the beginning of March, you may be greeted with the effects of the northern winds. Their arrival can produce swells that may make it difficult to drop anchor.

However, this is the beauty of sailing, instead of not visiting the island at all, just head for another calmer port on the island and continue your vacation.


Advantages of Having a Crew on Board

Choosing to charter a yacht at a time when there are the least vacationers is always a good idea. Using a charter to sail the Caribbean allows you to enjoy the voyage while someone goes about the business of the daily chores and cooking.

Another advantage of having a captain and crew on board is the experience they bring when it comes to clearing customs.

A charter captain is knowledgeable when it comes to monetary rates and documents needed to gain access to the island once you arrive in port.The captain can help to speed the process of entry so you can go on your way exploring the island.


What to Do Once You Arrive?

Now that you know what the weather is like during this time in the Caribbean, and the best way to vacation there, now we need to know what is there to do once you arrive?

Well besides the obvious of playing on the beach and water activities, this is the time when Carnivale is celebrated.

By preparing in advance by researching the island destination, you can arrive in time for the island celebration and join in the festivities, eat the delicious delicacies, and take pictures of the radiant colourful costumes native to each island culture.

Where to Drop Anchor?

One suggestion is to drop anchor in the location of the Windward Islands. This allows you to experience sailing between the islands of Grenada, St. Lucia, St. Vincent, and Martinique to experience French culture and British history.

There are plenty of open water between the islands to enjoy peaceful sailing in this part of the Caribbean that is loved by sailors and called one of the worlds’ best sailing destinations.

When planning a vacation. the time to take a trip sailing the Caribbean is before hurricane season, between February and June. Then you will experience warm sunshine and calm winds as you travel from island to island enjoying your sailing vacation.

Do you know when it’s the best time to sail in the Caribbean? Please let me know in the comments below


  1. I’ve never been the carbbean, but to does look lovely. It’s those deep blue waters and the clear blue skies that make it to beautiful. It’s a very long way to go, but I’m sure it must be worth it.

  2. Great article. I found it useful to know the best times to charter. I’ve always wanted to do this! Thanks for the information. Your pictures are beautiful!

  3. Beautiful places you show to Vacation on a Yacht. I have friends I will have to send to your site that likes that kind of vacation. Nice Job!

  4. Great information and good helpful advice for anyone taking a sailing holiday around the Caribbean, You give the best time to sail and also give the temperature. \\\\\\good advice also on what to do once you dock like researching the islands entertainment calander. A great post and with great content and fabilous photo’s.

  5. Excellent information on sailing in the Carribean and I totally agree that it’s a good plan to have a Skipper and crew. It does make life a lot easier. I have a friend who charters sailing boats in Greece and the Skippers know the people at each port and can get everything done pronto.
    Unfortunately I won’t be getting to the Carribean anytime soon so I’ll just have to bathe in the stunning photographs for now.

  6. Sailing in the Caribbean sounds amazing. I would love to go from island to island seeing the festivals and playing in the water. Maybe drink some rum on the beach 🙂 you have some good advice on when to do it for sure, nothing could ruin a vacation quite like a hurricane.


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