Destinations and routes

Discover the Caribbean aboard a sailboat

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  • Blog photo
By Álvaro Casanova y Jason Loughnane
21 November, 2019
When we associate the Caribbean Sea with nautical activity, the stories of pirates and sailors that we have enjoyed so often through literature, film and other media immediately jump into our heads. They are stories from another era where these waters of the New World were crossed each day by a multitude of navigators, who, whether operating on commerce or piracy, made the sea their usual place of work. The exotic pleasures, the natural wealth of the area, and the endless legends about the treasures that were supposedly hidden there gave color to the motives of these navigators.

Although the myths about gold and hidden riches have been forgotten, the Caribbean continues to remain a precious sea for boating enthusiasts. The aforementioned incentives are joined by another very important one for Europeans: the pleasant temperatures. It is no secret that the climates of autumn and winter that the Old Continent experiences from October to March is a deterrent for many people when sailing. For this reason many skippers decide to cross the Big Pond and head towards America in search of a more desirable place to hoist the sails and enjoy the sea.

If you want to discover in person the best spots to sail in the Caribbean, Sailwiz has several plans on offer to get you aboard a sailboat with an experienced skipper at the controls, and navigate this legendary sea in a safe and enjoyable way.
Table of Contents
To show
  • How do I prepare to sail in the Caribbean?
  • The best sailing spots in the Caribbean
  • Tall Ships: The Ultimate Classic Essence

How do I prepare to sail in the Caribbean?

For many Europeans, the biggest obstacle to sailing the Caribbean is probably the fact that it is a far from home. This means investing additional time in finding and choosing a way to get there, in addition to booking more days off for the holidays in order to make it worth it. One option that many have in mind to alleviate the first aspect is to cross the Atlantic on a sailboat. In this way, you will be able to quench your desire to navigate for about three weeks onboard, allowing you to then explore the Caribbean at your own pace, either from the boat or on land. But if you decide to sail directly there, it is important to book return flights with schedules that give you a certain margin, especially after boarding.

It is also necessary that you have all the documentation in order and have a valid passport. You may have chosen to navigate an island where it is not mandatory to present this kind of document and it is enough for you with a national identity card, as is the case for example in the French overseas territory of Martinique. However, the most logical thing is that you want to sail more than one island and to disembark on many of them you will need to be in possession of the aforementioned passport. If, as in many cases, you want to navigate the Caribbean between the months of December and May, it is also advisable to study the temperatures well, and pack according to the climate that you will find there.

A very important issue is to choose the right boat and captain to sail with, relative to the trip. Climbing aboard a good sailboat and under the command of a skipper with experience in the area increases both the comfort and safety of the sailing itself. The sailing plans in the Caribbean that you will find in Sailwiz are carried out aboard sailboats of proven quality and with skippers of proven experience, so you can enjoy much more peace of mind when enjoying your nautical experience when sailing these seas.
A spectacular beach in the Dominican Republic
A spectacular beach in the Dominican Republic

The best sailing spots in the Caribbean

While it is true that the entire Caribbean hold the virtues that we have previously mentioned, the different islands washed by this sea have very different characteristics from each other. These are the most frequented areas by sailors that sail the seas aboard their sailboats:
  • Cuba and Dominican Republic. Two large islands that have ideal coasts to travel to by ship. The Cuban keys are must-see exploration, as well as the coastal seabeds if you have diving as a hobby. Not to mention all the well-known tourist attractions you will find when setting foot on land and going to one of the most important cities ...
  • Antigua. If what you are looking for on your journey through the Caribbean is an island that encompasses everything that falls under the adjective "paradise", this is your place. Its beautiful and endless beaches divide the turquoise waters from an earthly space where virgin nature coexists with an architecture and culture that runs centuries deep.
  • Guadeloupe, Martinique and Dominica. Three neighboring islands but very different from each other. Guadeloupe and Martinique surprise the curious fusion between French and Caribbean cultures, while in Dominica you can contemplate the green nature that permeates every piece of land.
  • Trinidad and Tobago. The southernmost islands of the Caribbean stand out for their rich beaches, which open the door to a tropical area where flora and fauna reflect the most spectacular biodiversity of this area.
  • Panama. The San Blas archipelago belongs to the Panamanian nation and is also counted among the favorite places of the Caribbean sailors, who see in these islands a perfect opportunity to definitely get away from civilization and discover, from the sea, all the beauty that in They hide.

Tall Ships: The Ultimate Classic Essence

Over the years, boat trips are increasingly safe and comfortable. Good materials, better construction techniques, constant revisions ... Everything designed to make the trip perfect. It is obvious that all parties win with these foresight actions, nevertheless, it is also true that some sailors miss  what those sailors could feel when they crossed the seas centuries ago. The answer to that desire is granted through Tall Ships, or tall-mast sailboats, boats whose classic design and large size have peculiar characteristics. In terms of sailing, there are also clear differences when compared to other sailboats of more standard appearance.

It is not very difficult to imagine that life onboard a Tall Ship can evoke something very similar to what sailors of past eras experienced. Imagine sailing the seas of the Caribbean aboard one of these boats, combining this delight of this classic ship with the comforts of the present day that we mentioned previously. Sailing aboard one of these sailboats is the ultimate experience for many sea lovers.

In Sailwiz you have at your disposal several plans to sail the Caribbean in one of these Tall Ships. You only have to look at the exterior and interior photographs to see what you will find upon embarking the vessel and, above all, when the candles are blown and the crossing begins.
One of the Tall Ship you can sail on if you book in Sailwiz
One of the Tall Ship you can sail on if you book in Sailwiz
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    Álvaro Casanova
    Booking manager in Sailwiz. If you are looking for a plan to navigate, you can write to me and I will find what you need. And if you have a boat, you are probably interested in sharing your boat activities with thousands of users.
  • Blog photo
    Jason Loughnane
    International Development Manager. Always on the search for new and exciting things to experience, my aim is to offer the Sailwiz community the best selection of sailing trips out there. I'm here to help you find your next (or first) sailing experience, or help you find crew members to join you on board. You can reach me at info@sailwiz.com.
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