A trip to the Caribbean is all about the adventures of the sea. Warm winds, crystal clear cerulean waters and the reflection of the moon on midnight waves… The ocean calls to all of us, and whether you’re the type to lounge on the sundeck of a day-trip yacht or you’ve always dreamed of captaining a vessel of your own, the Caribbean is the answer. These islands are anyone and everyone’s perfect sailing destination.

If we still don’t have you convinced, rest assured that you can sail the Caribbean entirely on your own terms. With varying levels of experience on deck, some travellers prefer to have a professional crew do the navigating, and others are ready to take on the task for themselves. You can make it as easy as hopping on a charter with a pre-set itinerary and simply ride the waves, or you can be in charge of your own craft and plan out the perfect journey step by step. Just a few hours on the water is enough for those who prefer coming back for a good night’s sleep in a private villa on land, while letting your boat double as accommodation is a much better option for those who want to round-trip the islands for a few days. See where we’re going with this? 

We wouldn’t dream of telling you how to spend your holiday, but we thought we’d put together some options for you. In this blog, you’ll find some of our choice sailing spots and on-shore stops along the coasts of our favourite Caribbean islands. Each of these could serve as the destination of a day-trip, or you could easily slot them into your very own island itinerary. Happy sailing!

caribbean sailing routes

Before you get started…

  • Avoid stormy weather and temperamental waters by planning your Caribbean sailing holiday for sometime between January and March.
  • You have three main options for renting a yacht or sailboat in the Caribbean: “bareboat,” “skippered bareboat,” and “crewed charter.”
  • You can book your vessel directly with a charter company or you can go through a charter broker. A broker will act as a travelling agency, helping find the right boat for you. If you’ve chosen to travel with a professional crew, a broker will make sure they’re a good match too.
  • There are plenty of great small businesses across the Caribbean that offer fully catered day-cruises with pre-set itineraries. If this sounds like something you’d enjoy, have a look at these excursions in Barbados, St Lucia & Jamaica.  


caribbean sailing routes

The gorgeous coral island of Barbados covers just 166 square kilometres where it lies far out to sea, 98 miles east of the West Indies. Alongside its endless white sand beaches, Barbados’ epic shoreline hides secret caves and underground lakes. Above ground (but underwater) you’ll find some unparalleled snorkelling opportunities here, often featuring friendly sea turtles. That’s not to mention the island’s beautiful tidal pools, and incredible surf spots. But aside from these gorgeous natural phenomena, Barbados has a very rich culture and history. While you’re docked at the charming seaside towns, it’s definitely worth having a wander and visiting some of the old plantations.


  • Port St. Charles is home to one of Barbados’ main marinas, which can offer overnight shelter for your boat if you’re on a longer trip. The port is also home to a very exclusive resort, but Heywoods Beach (like all beaches on Barbados) is open to the public! 
  • Port Ferdinand is another large marina where you can dock overnight. If you find yourself doing so, walk along the quay and stop at the Fish Pot for an excellent dinner ashore.
  • Making your way south along the coast, you’ll come across Reeds Bay, a quiet and unspoilt beach which is ideal for a swim and a picnic on the beach. 
  • Leaving your boat in Alleynes Bay, pop into the iconic Ju Ju’s for a cocktail!
  • If you’re ready for a relaxed afternoon, make your way to the waters off Folkstone Marine Reserve and snorkel its brilliant waters. Among the fishes, you’ll be able to spot sea anemones, sea lilies, corals and sponges.
  • On the shores of world famous Sandy Lane Bay, head onto shore for lunch at the lush Sandy Lane Hotel and a bit of water sports by the beach.
  • As you close in on the city of Bridgetown, anchor in Carlisle Bay and take a tender to Browne’s Beach where you can lounge on the beach with some Rum Punch – and don’t forget to keep an eye out for those turtles!
  • Bridgetown is also home of  Barbados Yacht Club & Barbados Cruising Club, the only two Yacht clubs on the island.

St Lucia

caribbean sailing routes

Little St Lucia lies at the heart of the Eastern Caribbean chain offering up beautiful palm-fringed beaches, expanses of untouched rainforests and, of course, the iconic Piton mountains. St Lucia is known for is champagne sunsets and clear starry skies, making it the dream destination for a romantic couples holiday. On a trip along its shores, you’ll come across waterfalls and luxury marinas, mineral baths and seaside art cafés. Something new and unexpected hides around every corner. You’re sure also to find that the locals are incredibly hospitable and that you’ll be well taken care of wherever on the island you end up.


  • At the very north of St Lucia, you’ll find Pigeon Island with its two beautiful beaches and old military ruins. You’ll get the best views if you hike all the way up to the old naval fort. 
  • Sail into Rodney Bay where the nightlife is lively and the food is fresh. And while you’re at it make a stop at the golden sands of Reduit Beach.
  • Pass by the spectacular vista of Choc Bay and take a swim in the still waters. If you keep making your way south from here, get onto shore and visit the nearby town of Castries.
  • The hurricane hole of Marigot Bay is not only a site of natural marvel but also the filming location of the original Dr Doolittle film! This is an excellent overnight anchorage and the nearby Marina Village is great for shopping and restaurants.
  • Take mooring outside Bennie’s Restaurant where your boat will be taken care of as you explore the surrounding area and marine park.
  • Anse Cochon is one of the top beaches to put on your itinerary, with amazing snorkelling and great surroundings for a picnic.
  •  Soufriere. It is booming with culture and makes a great base for inland explorations. From here you can hike the majestic Pitons and the visit drive-in volcano at Sulphur Springs.


caribbean sailing routes

Jamaica is one of the most colourful islands you’ll ever come across, even by Caribbean standards. Its tropical landscape blooms in all the hues of a rainbow, and the wildlife is just as exotic. Everything you have in mind when you’re dreaming about the Caribbean can be found on Jamaica. Making stops along the island’s 350 miles of lush coastline you’ll be able to indulge in all kinds of adventures, waterfall climbs to rainforest hikes and epic snorkelling adventures. You’ll also find that the local cuisine is unlike any you’ve tried before. Explore a whole world underneath the turquoise waves or dig your toes in the sand… this truly is paradise. 


  • Any good trip to Jamaica begins or ends in the capital of Kingston where all the urban action happens and Kingston Harbor dominates the shoreline.
  • Head east, to where Port Morant offers up stunning scenery. Dockage is free, so you can explore the area for as long as you’d like.
  • Rounding the tip of the island now, stop off at Port Antonio and the world-renowned Errol Flynn Marina which is known as one of the best sailing spots on Jamaica where enthusiasts from all around the world cross paths.
  • You’ll encounter the most authentic Jamaica at Orcabessa, as well as an excellent fish sanctuary and turtle-hatching programme.
  • Ocho Rios might hit on the touristy side, but the nearby St Ann’s Bay and Discovery Bay are where the cruise ships dock, inevitably filling the area with lots of fun activities.
  • Treasure Beach is a calm and peaceful area to spend some time relaxing.
  • Make a stop at the Errol Flynn Marina which is known as one of the best sailing spots on the island. Located in Port Antonio, sailors from all around the world cross paths here.
  • In Falmouth, you’ll find some incredible architecture in the Falmouth Historic District, definitely worth a short visit at the very least.
  • Montego Bay is the home of the Montego Bay Yacht Club, another can’t miss along the coast with its stunning beaches. 
  • On the west coast of Jamaica, stop by the beautiful and protected Negril which is known to be one of the most beautiful coastal areas in the world with its stunning Seven Mile Beach.
  • Last but not least, a tour up the Black River is one of the most unique experiences you can have while sailing Jamaica.

Have we got you in the mood yet? If you eager for more, check out our other blogs on the Caribbean. Or perhaps you’re looking for a great place to stay on the islands? In that case, go straight to our Caribbean villas page! 

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