Where to Sail in the Caribbean – 5 Best Sailing Destinations!

As one of the premier sailing destinations in the world, the Caribbean needs no introduction to its many attractions, both natural and cultural.

The region is home to some of the most stunning islands anywhere in the world, rich tropical landscapes, spectacular weather, picture postcard beaches, and clear blue waters.

The conditions for sailing are, for the most part, ideal, while the extensive sailing infrastructure ensures that yachtsmen are never too far away from their provisioning, fueling, and other assorted needs and requirements.

Nevertheless, it is also true that, geographically, the Caribbean is a huge region with many island nations and jurisdictions.

And most importantly, not all of them are equal in terms of natural attractions, amenities, and even security. It, therefore, becomes important that you know where to sail in the Caribbean to get the most out of your sailing adventure in this region.

The theme of this article introduces some of the best-known sailing destinations in the Caribbean and tells you what sets them apart from the rest.


St. Maarten

Probably one of the most coveted destinations in the Caribbean, St Maarten is an unusual island governed as it is by the twin jurisdictions of France and the Dutch Antilles.

The idyllic island, with its white sandy beaches and unsurpassed beauty, has established itself as a prime sailing destination.

With other neighboring islands such as St Bart’s, St Kitts and Nevis, and Anguilla in close vicinity, visiting St. Maarten allows yachtsmen to see and explore more of the Caribbean.


The weather on this island is warm throughout the year, with an average of 27 degrees Celsius. June to September marks the late summer and onset of fall when tropical storms become somewhat frequent.

Aside from this, the weather is perfect and stable throughout the year, leading to immaculate sailing weather.


For the visiting yachtsmen to this island, there is no shortage of activities. From the popular Regatta at Great Bay in Philipsburg to luxurious marinas, St Maarten stands out as a giant sailing playground.

In addition, the island offers excellent opportunities to explore the culture of this island on both its French and Dutch sides.

For those in need of retail therapy, St Maarten’s reputation as an international shopping destination would cause much excitement.


St Maarten has deservedly earned the title of being the gastronomic capital of the Caribbean, on account of its thriving restaurant scene.

The exotic mix of local Caribbean cuisine with French and Dutch influences has created a culinary experience that is unique to St Maarten.

Whether you are looking for an upscale fine dining experience or something more lowbrow, you are sure to find something agreeing with your palate among the 300 restaurants on this island.

Beach in St-Maarten island

Leeward Islands

Located to the east of Puerto Rico in the Lesser Antilles of the Caribbean, the Leeward Islands offer an enchanting mix of unspoiled beaches, top-notch shopping options, and a tantalizing cuisine.

No surprise, therefore, that the Leeward Islands, with Anguilla and St Bart’s being the most popular, have become increasingly popular among the sailing community.

The French influence in this part of the Caribbean also brings a bit of Mediterranean magic to your overall experience.


These islands are close to St Maarten and experience similar warm weather throughout the year. The islands here have natural harbors, although not all are protected from all sides. There are also marinas with all the modern amenities and provisioning facilities that yachtsmen typically require.


There is no shortage of onshore activities on these islands, with their numerous natural and man-made attractions.

There are countless pristine beaches waiting to be explored, while the chic shopping establishments are sure to provide you with a truly international experience.

If you have a taste for adventure, there are a lot of options for daring water sports.


The French influence on the local culture, especially at St. Bart’s, is most visible in the cafes and restaurants on this island.

Aside from this unique fusion of French and local cuisine, visitors can sample cuisines from the world over, with modern twists by experimental chefs.

Whether it is gourmet restaurants, or a romantic dinner overlooking the calm blue sea, you can find it all on these islands.

View on Leeward island


Located in the eastern Caribbean, as part of the Leeward Islands, Antigua has earned itself a name as one of the premier island getaways of the region.

The colonial past of this island, thriving local culture, spectacular natural beauty, and a variety of shopping and entertainment options have made Antigua a favorite among the sailing crowd.

Antigua is also the largest English-speaking jurisdiction in the Caribbean. Part of the island country of Antigua and Barbuda, the island is endowed with hundreds of pristine beaches and coral reefs.


The weather is warm and ideal for sailing throughout the year except during late summer and early autumn when the island experiences sporadic storms.

The island has a number of top-notch marinas and anchorages, making it ideal for the sailing community.


There is no shortage of activities on this island for the visiting yachtsmen. If you are lucky to visit during the Antigua Race Week, one of the most coveted regattas in the world, you can witness professionals compete for the prestigious Lord Nelson’s Trophy.

In addition, Antigua affords top-notch scuba diving, snorkeling, and diving opportunities. If you want a slice of the local culture, you can head down to the bustling streets of St John’s.

While romantic couples can always head to the dozens of virgin beaches to admire some of the most astonishing sunsets ever.


Antigua has a unique cuisine of its own, distinct from other nearby islands. For example, their national dish called fungi, is a pot stew made of several kinds of meats and vegetables that you would not find anywhere else.

While seafood obviously dominates the culinary landscape, the colonial past of this island means that you would discover some truly unique dishes in Antigua.

Beach in Antigua


Located on the southernmost tip of Grenadines, the island country of Grenada comprises a total of 7 islands. With its capital at St George, Grenada lies in close vicinity to Trinidad and Tobago and St Vincent.

Grenada and the 6 islands that make up its territorial jurisdiction are heavily influenced by the European and South American settlers’ culture, visible in their architecture, language, and cuisine.


Quite like most of the Caribbean, the weather here is warm throughout the year, making it ideal for sailing. While there are tropical storms during the onset of early fall during the months of September, the weather is still good enough for the sailing crowd.

In addition, these islands are blessed with some beautifully protected harbors and anchorages for the yachtsmen to secure their yachts.

The sailing infrastructure in Grenada is highly developed, enabling visiting yachtsmen to meet their provisioning and other related needs and requirements.


Grenada has earned itself a reputation for its beautiful and pristine beaches, calm and clear waters, and stunning coral reefs. Visiting yachtsmen would find excellent opportunities to unwind at these superlative beaches and take part in exciting water sports and related activities.

Whether it is scuba diving, snorkeling, or surfing, or enjoying a water scooter ride, there is no shortage of adventure sports in Grenada.

In addition, there are wonderful opportunities to enjoy the local culture at the some of the most wonderful museums in all of the Caribbean.


The confluence of European and South American settlers in Grenada has meant that the local cuisine here is a unique and delicious fusion.

Aside from the wonderful local cuisine, there are top-notch fine dining restaurants in Grenada, allowing visitors to sample tantalizing cuisine from the world over.

Needless to say, just like all Caribbean destinations, you can expect nothing but the finest when it comes to seafood.

Restaurant on the water in Grenada

St Vincent

Part of the Windward Islands, St Vincent, and the Grenadines are a group of the island close enough for yachtsmen to easily sail between them. Unlike some of the more visited regions of Caribbean, St Vincent is still relatively less developed and less explored, adding to its idyllic charm.


Aside from the storm bearing months of late June through September, the weather in this region is ideal for sailing.

During the winter months, the winds are mostly from the north to south, enabling a leisurely sail southwards to Union islands.

While sailing upwind north can be difficult, the islands are close enough and yachtsmen can accomplish a round trip within a week.


As mentioned above, St Vincent is one of the less developed parts of the Caribbean, adding to its idyllic appeal. However, the unspoiled natural beauty of the island offers plenty of opportunities to unwind.

For example, the volcanic island of St Vincent itself offers the best trekking opportunities in the whole of Caribbean.

The islands of Bequia, Mustique, and Canouan offer mesmerizing beaches that are a treat for the sore limbs.


St Vincent is home to old West Indian-style plantation houses turned resorts that offering a taste of its colonial past.

Aside from that, you can expect freshly caught seafood prepared in the most delicious of local flavors. The advent of French and other European influences has ensured that you are never too far away from the flavors of old Europe.

Newer restaurants established by daring and experimental chefs, trained in the latest culinary techniques, offer modern twists on local delicacies.

Two barman in a bar in St-Vincent


The Caribbean, owing to its tropical climate, is particularly favored by the sailing crowd as they can visit the region any time of the year.

The incomparable natural beauty, rich natural culture, the influence of European settlers, and delicious local cuisine has ensured that the Caribbean holds a special appeal to one and all.

In this article, I have highlighted some of the top regions where you can sample the very best of Caribbean sights and sounds.


If you have more recommendations to make, do get in touch via the comments section below.

8 thoughts on “Where to Sail in the Caribbean – 5 Best Sailing Destinations!”

  1. Hi Daniella,
    What a beautiful site! I’ve never been sailing but I love the ocean and some of my best vacations have been spent enjoying the beach. It’s been many years but right now I can hear the waves, feel the sand and taste the seafood 🙂 For someone primarily interested in snorkeling and relaxing on the beach, which of these 5 destinations would you recommend?

    • Hi Linda,

      Thank you for the compliment, I am glad you like my website:)

      I would personally suggest you, Antigua as it is the top notch place for snorkeling and scuba diving, you will enjoy snorkeling among tropical fish and fantastic coral reefs. Also, there are 360 beautiful beaches to delight and relax on Antigua island. Without a doubt, this island would be the perfect place for your requirements.

      If you need to know additional information, please don’t hesitate to contact me, I’ll be very happy to help!

      Thank you for the comment.

      Have a great day!

  2. Hi Daniella, I love the pictures you have of the Caribbean, it’s so enticing that it is making me feel like getting on a plane to go visit and enjoy some the delicious cuisine that you can experience in the Caribbean. Being from the Caribbean myself, I can surely understand your love affair with the warm weather, the food and the beaches.

    • Hi Reneea,

      I am glad that you like the pictures, and that it makes you want to visit right away:) Nice compliment, thank you!

      Hmm, you are from the Caribbean, that’s great, I am sure you enjoy every moment over there, such beautiful places to visit! However, feel free to share some of your experiences in the comment, only if you feel like doing it:) It will be a pleasure to hear from you!

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

  3. Hey, love this site, I’m currently learning to sail after my wife gave me a “Best Places To Sail” book for a wedding present. I love the thought of sailing round the caribbean like a pirate, and you make it sound amazing, but the one thing i’ve heard is it can be pretty expensive. Any idea of the costs involved?

    • Hi Dave,

      That’s wonderful that you learn sailing, I am glad for you:)

      The cost of a yacht charter will depend on many factors, for example the length and the year of the boat, the destination, with or without a crew, etc..

      A sailing trip can be really affordable, especially if you sail with a group of friends or with family, why? Because the price of the boat will be divided by the number of passengers. If you rent a room in a hotel, you won’t be able to split the cost with others, generally, it is for a couple, well, as far as I am concerned 🙂 However, there are a lot of advantages of renting a yacht for a vacation.

      Here is a great article to read about yacht charter vs hotel.

      If you need to know further details, please don’t hesitate to contact me, I’ll be more than happy to help you!

      Thank you for the comment and wish you a fantastic day:)

  4. Well that was quite a read!! Now I want to go sailing in the Caribbean!! I love how you point out not only what activities you can participate in, and what the local cuisine is like, but also the weather – obviously sailing is quite dependent on particular weather fronts 🙂 I love seafood and so this would be heaven to me, eating various dishes with all the different cultural influences. But I have to say I’m bemused at the national dish of Antigua…. fungi….? Haha! I’m kidding, it sounds delicious 🙂

    • Hi Jyl,

      Great, I love humor, it makes you live longer:)

      I am glad you found the article helpful and I hope you will get the best of it!

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

      Have a wonderful day!


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