Top Sailing Destinations in the Caribbean – 7 Marvelous Places !

Ever thought of a place where you can contentedly relax and find utmost peace among the best water sceneries in the world? Well! The Caribbean is certainly the place you can’t go wrong when it comes to this.

From the calm waters admirably surrounded by the white sand beaches to the deep-sea volcanoes whose peaks are absolute “out of this world” and through the alluring palm trees that are always bending down over the tranquil waters to create such an overwhelming feeling, this renowned destination is definitely worthwhile for your sailing yacht ride.

So! Exactly which are the top sailing destinations in the Caribbean? Undoubtedly, this might be one of the biggest questions running through your mind right now, bearing in mind that there are over seven thousand islands, each with its unique beauty.

Without a doubt, it would be very difficult to single out the best of them all. However, there are seven destinations that absolutely stand out and that you can’t afford to miss setting foot on if you choose the Caribbean as your sailing destination.

Here is a recap of these marvelous places.

Caribbean Sea


This historical island is not only the center of natural beauty; it also encroaches with diverse sites and rich history that indeed make it a prime destination.

The list of things to do and see is endless; from the extensive pristine white sand surrounding the beach, to the calm irresistible blue ocean and the famous dockyards that date back to the 18th century,

Antigua is categorically a destination that deserves to top on the list of your priorities. If you find British history appealing, then this is the place to be. The British forts sit just on top of the green hills while their indigenous canons lie down at the bay.

The architectural designs basically date back to the colonial times where houses were typically painted white making the place an absolute “paradise” to have utmost fun.

If you think that that is all; wait until sundown when the fun actually begins with the delicious meals literally filling the tables.


St Barts

This is one of the most classy and luxurious destinations in the Caribbean typical for exclusive tours and holidays. In essence, everything about this island is exceptional especially when it comes to world-class restaurants and shopping boutiques.

This is basically a place to sail with your family on a holiday and watching or playing water sports including wreck diving at Gustavia port.

The saline beach offers one of the best views to watch as the sun bows down for the nightfall while the sandy stretches of the beach ensure that you don’t miss a thing on the island.

The fun does not end there; you can enjoy an aerial view of the island while in a plane that is always ready to take you on this journeying tour.

St Barts


This is one of the most esteemed islands in the Caribbean. In a real sense, the island is home to multiple stylish resorts that attracts “VIPs” from across the globe.

The environment ensures that you never get bored with the ever-sparkling water scenario ensuring you have memorable moments to carry back home.

When it comes to water sports, every single one of them is included ensuring that you never miss coming back for more and more fun.

Convenient enough, the Island is located near two of the most developed islands in the Caribbean, i.e. St Barts and St Maarten, therefore attracting high caliber designs and resorts.


St Maarten

With such a rich history of how the island came to be, St Maarten enjoyed the growth support of both the Dutch and the French who anciently divided it among themselves.

Basically, everything about this island is breathtaking; right from the mesmerizing water sceneries to the beautiful nightlife experience that you wouldn’t get enough of.

The mouth-watering dishes definitely spur the fun making the island one of the deserving sailing destinations in the Caribbean.

St Maarten

British Virgin Islands

These groups of islands (approximately 60 island and islets) are unquestionably the most popular destinations in the Caribbean. If you think that you have seen it all; wait until you get to these islands where you are sure of finding “the mysterious” wonders of nature.

The BVI island basically features every aspect of beauty; the palm trees that tower at the white sand beaches thoroughly ensures you don’t miss a thing when it comes to beach attractiveness.

Your tour on the island would not be complete without snorkeling in the serene waters where tropical fish have literally made a home and the wrecks and reefs are abundant.


The Grenadines

Surely one of a must visit islands in the Caribbean is the Grenadines. In actual fact, this is the “home of splendor.” Every moment that you spend on this island will certainly be worthwhile your time on this magnificent islet.

The sunny Tobago beaches offer extraordinary memories of the island especially if you enjoy swimming with the gorgeous sea turtles.

Obviously, your tour wouldn’t be complete without a visit to the Mustique for the supreme view of the island’s attractiveness.

Mustique Island


Notably the most famous and largest destinations of the Caribbean, Cuba offers ultimate tour satisfaction. The Cuban culture is indeed one to “die for” with a stay in Cienfuegos ensuring you fully integrate with the locals.

The spotless beaches are an absolute wonder to look forward to with palm trees flavoring the already gripping setting.

If you love exploring the underwater, you have not been left behind either, with the Cuban water offering the safest conditions to ensure you just do that.


Whether you are a first-time sailor or a seasoned captain, you certainly can’t get enough of this thrilling yacht destination.

In fact, every moment, from the rise of the sun to its downfall when the rays are startlingly shining over the waters, is absolutely breathtaking and etched in your mind.

The Caribbean is certainly the place to be this winter; and which other way can you enjoy this wonderful beauty more than to charter sailing yacht entourage which is absolutely stylish, comfy and worth every penny you spend on it. So, book your space now and cruise your way to these beautiful islands.

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31 thoughts on “Top Sailing Destinations in the Caribbean – 7 Marvelous Places !”

  1. Oh I would love to go to the Carribean! It looks so beautiful and peaceful.
    I would love to swim with sea turtles, can you only do this at The Grenadines?
    A trip to the Carrribean would be really peaceful, there is nothing more serene than snorkeling and watching all the sea life!

    • Hi Lynne,

      Yes, the Caribbean is magical without a doubt!

      You can do a lot more than swimming with sea turtles:)

      Here are some ideas; you can do some hiking in the volcanic mountain of St Vincent, snorkeling in the Tabaco Cays, do some shopping in Clifton Harbour, you can stroll in the morning market in Kingstown, the capital of St Vincent, you can visit the botanical garden in St Vincent, and do so many other great activities. I wish I could write everything in one post, but I am afraid I won’t have enough space for it:) Fortunately, this is not the last blog, There are more coming soon!

      Thank you for the comment and I wish you a great day!

  2. Wow. The beautiful scenic photos that you have included make it very difficult to just choose one destination! I feel that you would almost HAVE TO take in the beauty of all the destinations listed! Do you have a favorite? What would you recommend for a Caribbean first-timer? How far in advance should I begin planning a charter?

    • Hi Nicki,

      Yes, you’re right it makes it really difficult to choose on of these beautiful destinations. I would have started my trip in Antigua as I love history, restaurants, and beaches.

      You need to book at least few months in advance to plan correctly a sailing trip, you can take the chance to book few days in advance, but then you take the risk not to be able to choose your boat and the destination desired, so take your precaution.

      Thank you for the comment

      Wish you a wonderful day!

  3. I wanted to let you know how impressed I was while looking through your website. For starters, visually it is stunning. The destination pics made me want to click further on to see and learn more about each destination. I imagine you should do quite well with your site as it definitely drew me in and kept my interest in the materials and information you presented!

    • Hi Mike,

      Thank you for the compliment, I am really glad you like the website because I put all my heart in it every single day:)

      Again, thank you and wish you a nice day!

  4. Hi Danielle,
    I am glad you enjoyed reading the article and the pictures.Yes, effectively these pictures are extremely attractive and I am sure many of us would do exactly the same, drop everything to sail to these beautiful islands right away!
    Thank you for the comment and I wish you to sail very soon!
    Have a wonderful day

  5. Hi Daniella,

    I would love to go to Cuba, where the exact place of the photo now! I’ve always wanted to go and yes as you say, it’s the place to die for! Also I’m interested in Antigua now, since you mentioned about British history, and I’m from Britain, I’d like to see what’s there. Caribbean islands are certainly exotic and each one seems to have its own character. Thanks for the great information!


    • Hi Ray,

      Never been to Cuba also, but plan to visit soon! Even though the population live in poverty, it still is one of the most popular destination in the Caribbean. Very attractive place!

      Antigua island is rich in history, if you want a melange of sensations, then Antigua is definitely the place to be!

      Thank you for the comment and wish you to sail soon!

  6. I love the pictures and it really gives a refreshing sight and very inviting and tempting makes me want to swim the waters. I never knew Carribean could offer a wide arrays of sailing destinations and I really find it so loving and serene. I would love to try different beach and island activities especially in Cuba.

    • Hi Jezza,

      Yes, it is very tempting like you said.The Caribbean is fantastic and so peaceful. I would have chosen Cuba as well 🙂

      Thank you for the comment!

  7. Wow Daniella, I knew that the caribbean was made up of islands, but 7 thousand! I have always wanted to go to Cuba but the other island that stands out to me is Antigua (although they ALL look amazing). One thing that attracts me to the caribbean is not only the beaches, but the history and mix of cultures and languages. I also love the architecture of the Antiguan buildings and think this could be such an interesting destination!

    • Hi Stacey,

      Yes, as I said in the article the Caribbean is an amazing destination to see. Cuba is on my list for the next sailing holiday! I was in Antigua last year and I would definitely go back there:) Not just because I didn’t have the time to view all the places, but this spot is a must to revisit again.

      Thank you for the comment and wish you to sail soon in the Caribbean:)

  8. Hi Daniella,

    These are all amazing destinations and the pictures that you have included are beautiful.

    In addition, one of my favourite places in the Caribbean is Jamaica. The beaches there are absolutely breath-taking, there are some great diving spots and the food is to die for. 🙂

    I think out of all the places that you mentioned I would be most intrigued to go to St. Barts, as the wreck diving sounds very interesting.

    Thanks for your great article.


    • Hi Vivia,

      I agree with you, St Barth is a beautiful destination, and definitely a place not to miss out!

      Yes, the Wreck diving site is very interesting, it would be a good idea to drop anchor and do some diving during your visit.

      Thank you for the comment, I truly appreciate it!

      Have a nice day:)

  9. Oh my god…these beaches are so beautiful! Just by looking at them makes me feel relax already. The Caribbean is definitely a must visit holiday destination for me. Can’t wait to soak in the sun while lying on the sandy beach sipping that glass of champaign. Thank you very much for sharing such great places.

    • Hi there,

      Well, you are right, there is nothing better than to soak in the sun and relax, plus a glass of champaign, Awesome idea! I would suggest you the Moet & Chandon, absolutely delicious:)

      Thank you for the comment and wish you a wonderful day!

  10. Hello, Beautiful places and photos you have good information.I love to travel have never been in Caribbean but I hope I will be able to go one day. My favorite place is Santorini Greece, have been there many times, but it is also nice to see other places. Anne Line

    • Hi Anne,

      Thank you for the compliment:) Santorini is a beautiful place to visit, I went there many time and I just loved it!

      Thank you for the comment and wish you to visit the Caribbean soon!

  11. Hi there,
    This basically made my mouth water for a break in the Caribbean – it doesn’t even have to be sailing, although I do love it! Right now, we are still having quite wintry weather including some snow showers and freezing temperatures over the last few days. I’ve never been to the Caribbean, but I thought your summary of some top destinations was really inspiring. I particularly like the sound of St Maarten. Is there a hurricane season in the Caribbean, or a time of year best avoided?

    • Hi Mara,

      Thank you for passing by and for the comment:)

      The huriccan season in the Caribbean runs from June to November, but not in all regions, for example in the US East Coast and along the eastern Caribbean, it is much busiest between August and September.

      I hope it helped and if you need more information, please don’t hesitate to contact me, I’ll be glad to assist!

      Have a wonderful day!

  12. I look forward to going sailing in these places you have reccomended. I am really looking forward to it, you have reccomended some beautiful waters and is incredibly breath taking.
    Well done these have been some great reviews and i love the articles you have been writing on your website.

    • Hi Matthew,

      I am glad my website inspire you:)

      Yes, I agree with you, the Caribbean is a beautiful place to visit especially by boat and let me know if you need any help with the planning; I’ll be glad to help:)

      Thank you for the comment and wish you a wonderful day!

  13. The Grenadines looks awesome, is there any place in particular where I can find some places like in the picture?
    I really want to make a trip to the carribbean this year, and I don´t want to take a cruise, I just want to go to the best place availble and relax for a week or two. You think the Grenadines is the best place for this?
    Thanks a lot for the tips 😉

    • Hi Keven,

      The Grenadines is a beautiful and a peaceful place to relax, Tobago beaches are exceptional, I am sure you will enjoy!

      Thank you for the comment and if you need any help, please let me know I’ll be glad to assist!

      Have a wonderful day:)

  14. Hi Daniella,
    I have never been to the Caribbean before but it does look stunning and very tempting.

    I fancy Cuba as we know a few people who have been and all say the beaches were spotless and a wonderful place for a holiday. However I would be happy to have a holiday cruise in all 7 of these destinations.

    I’ll let my wife take a look and we’ll make a decision.
    Which place would you pick for a first timer?

    • Hi Simon,

      Yes, I totally agree with you, these Caribbean islands are absolutely beautiful, there is no doubt about it!

      To answer your question about which place to choose for the first time sailing, it will depend on your wishes.

      I personally like Cuba because this island just attracts me so much so it’s hard to say.

      All of them are completely different and that’s what make them unique and beautiful!

      Thank you for the comment and if you need more information, please don’t hesitate to contact me, I’ll be glad to help:)

      Have a wonderful day!

  15. I just love going on a cruise vacation because I love traveling and also the water. It’s the perfect combination for me. And these places looks heavenly and just perfect for going on a cruise vacation. Thanks for this visual treat.

    • Hi Mallick,

      Indeed, cruising is a fantastic way to enjoy visiting beautiful islands and all sorts of watersports.
      As you said, the Caribbean is a real paradise!

      Thank you for the comment and wish you a lovely day!

  16. I am a sucker for beaches, sand, sun and the ocean, and these photos have me drooling! I am heading to St Marten next month (along with a few other ports), and I cannot wait! Cuba and Antigua are two places that have peeked my interest after reading this. I am going to have to include them in my next cruise. I live in Florida, so the Bahamas are close and fairly inexpensive. I am not sure where Cuba and Antigua are to the states?

    • Hi Matt,

      Antigua is about 1200 miles ( 4 days at 10-knots vessel speed) away from Florida and Cuba about 300 miles 1 to 2 days at 10 knots vessel speed) from Florida.

      I hope it helped! Let me know if you need more info. I’ll be more than happy to help!

      Thank you for the comment and wish you a fantastic day!


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