March 5, 2024

12 min


Sailing Caribbean Waters: the Rubicon 3 Guide for Sailors

st lucia pitons

Ready for an unforgettable sailing adventure? Look no further than the Caribbean. With its endless exotic destinations, constant winds, and crystal-clear waters, this sailing paradise offers an experience like no other. From the soft white sands of its beaches to the vibrant underwater world and delicious cuisine, the Caribbean has everything to make your sailing trip exceptional. Trust us – don’t miss out on the opportunity to discover this stunning part of the world, encompassing hundreds of unique and breathtaking places that will leave you in awe.

If you’re interested in sailing in the Caribbean and want to know more about the best tips and recommendations for your trip, you’ve come to the right place. In this article, we’ll cover:

  1. What makes sailing in the Caribbean so special
  2. The best seasons to sail. in the Caribbean
  3. The sailing conditions you can expect
  4. The state of the islands and their infrastructure
  5. The costs involved
  6. The best sailing destinations
Tobago Cays

Why sail in the Caribbean? 

The Caribbean is a beautiful archipelago with over 700 islands, cays, and islets, each offering a unique blend of history and culture. This is part of what makes it such a perfect destination for sailing enthusiasts, as it all but guarantees an unparalleled sailing adventure along with perfect sailing conditions. The region is one vast expanse of azure waters and sun-kissed islands, where one can spend years exploring and still leave with many secrets undiscovered (meaning of course you need to come back!)

You will find some of the most beautiful islands in the world, including the British Virgin Islands, Antigua and Barbuda, Saint Martin, Guadeloupe, Dominica, Martinique, Saint Lucia, Saint Vincent and the Grenadines, and Grenada. For practical purposes, the region encompasses larger nations like Cuba, the Dominican Republic, Haiti, and Puerto Rico, as well as the quaint Dutch ABC islands of Aruba, Bonaire, Curacao nestled near South America, along with Trinidad and Tobago.

crew sailing in the caribbean

The Leeward Islands encompass Antigua in the north, then Guadeloupe, Dominica, Martinique and St Lucia, making for a wonderful adventure. They are only 250 miles from one end to the other, so you have almost line of sight day sailing and an endless list of spectacular places to explore.

To the south of them, St Vincent and the Grenadines, also known as the Windward Islands, are a tropical paradise, with the film star favourite of Mustique and the world famous nature reserve of the Tobago Cays as their absolute stars.

To the west of the islands, Jamaica makes for a very special downwind sail in the trade winds and if you dare, Cuba is one of the most wonderful and off the beaten track adventures imaginable for a sailor.

Martinique slaves

The Caribbean is great for:

  • Recreational sailors who are looking for some leisurely sailing, exploring and fun. The Grenadines are particularly good for this, as are the BVIs although they are increasingly commercial and crowded.
  • Offshore sailors looking to head off into the Caribbean Sea and take on a more challenging passage. The powerful North Easterly trade winds are perfect for this type of sailing. One of the great passages is to sail from the Leeward Islands to the exotic locations of Jamaica or Cuba.
  • Divers and coral reef seekers will love the underwater scenery, particularly of the Grenadines and Grenada archipelago and the Tobago Cays.
  • Explorers will not be able to get enough of the volcanoes, waterfalls, wildlife, flaura and fauna and rainforests on these islands. Every time you dock or anchor somewhere, the adventure is only just beginning
  • Lovers of dance, flowers, rum and rich fauna and flora will stay cheerful anywhere in the Caribbean

12 Days of Adventure: The Leeward Islands: Emeralds Of The Caribbean

What is the best sailing season in the Caribbean?

The Caribbean sailing season runs from January through to May. During these months, the weather conditions are more stable, the trade winds are steady, and the temperatures are comfortable. This period also avoids the hurricane season, which poses a high risk from June through November, with the most severe weather usually occurring from August to October. During the peak season, sailors can expect warm, sunny days, cooler nights, and minimal rainfall, making it an ideal time to explore the crystal-clear waters of the Caribbean both for novices and more experienced sailors.

Caribbean turtle

What are the sailing conditions like in the Caribbean?

When sailing in the Caribbean, you’ll encounter the northeast trade winds that blow steadily, allowing you to avoid worrying about sudden changes in the wind direction or strength. This makes it a great sailing ground for novice sailors. That said, there are poeriods of calm and sudden squalls can also hit, so you must always be vigilant. If you are sailing on the Atlantic side of the Antilles in the northern Caribbean, you’ll experience the impact of the Antilles Current. This flows in a northwest direction and merges with the powerful Gulf Stream above the Bahamas.

It’s important to be really careful of hidden dangers like coral reefs or shallows that may catch you off guard. Remember, not all obstructions are marked on maps or in applications so once you get near any dangers, you need to have someone on the bow keeping a sharp lookout. beyond that, hoisting someone up the mast and having them watch from the spreaders will give you an even better guide. Try to avoid sunset and sunrise, as you will struggle to see underwater hazards.

St Lucia Pitons

It is not advisable to go on night sailing trips between the Caribbean islands, even though it may seem a short distance and an appealing idea. The visibility of objects and coral in the shallow waters is almost non-existent during the night. There is also always the risk of being harrassed or attacked and having no one able to see you or be around to help.

When navigating between islands that belong to different countries such as St Lucia to Martinique, it is important to remeber the need to check out and check in and the various customs formalities. You will need to make sure you arrive at a designated “port of entry” for the specific island and register there. You can find these on This process can take anywhere from a few minutes to several hours, so it is important to consider this when planning your route. Additionally, it is not uncommon for customers inspections to occur at random intervals, so it’s best to be prepared for these as well.

yacht racing

The Caribbean Offshore 1000

What is the sailing infrastructure like in the Caribbean?

The Caribbean islands have a well-developed infrastructure that caters extensively to the needs of sailors and yachting enthusiasts. This region is a popular sailing destination and has established high-quality marinas, boatyards, and services across various islands that support a wide range of sailing activities. Let’s take a look at the available infrastructure:

Marinas: Numerous marinas dot the Caribbean islands and offer various services including berths for yachts of all sizes, electricity, water, fueling stations, and more luxurious amenities like restaurants, showers, and shops. Some marinas also provide customs and immigration services to facilitate the entry and departure of international sailors.

Boatyards and Repair Services: Access to repair services and boatyards is obviously crucial for maintenance and unexpected repairs. Many islands have facilities equipped to handle everything from minor repairs to major overhauls, with skilled craftsmen and technicians available to ensure yachts remain in top condition.

Sailing Schools and Charters: The Caribbean offers several options for those looking to learn sailing or charter a yacht for their adventure. Sailing schools offer courses for all skill levels, while charter companies provide a range of vessels from bareboats to fully crewed luxury yachts. Rubicon 3 believe in real world training and combining learning with actual adventures and our Caribbean adventures will give you this in spades

Provisioning and Supplies: Provisioning is easy with access to well-stocked supermarkets, chandleries, and local markets that offer everything from fresh local produce to marine supplies and equipment.

Safety and Rescue Services: The region is equipped with coast guard and safety services to assist in emergencies. Many areas also have well-established VHF communication networks for weather updates, navigation warnings, and emergency calls.

Anchorages and Mooring Fields: Besides marinas, there are numerous protected anchorages and mooring fields available for those who prefer to stay on the hook. These offer a more natural and often secluded experience, with guidelines and fees varying by location.

Navigational Aids and Facilities: The Caribbean waters are marked with buoys, lights, and other navigational aids to support safe navigation. However, sailors should always be prepared with up-to-date charts, GPS, and possibly radar to navigate safely, especially given the coral reefs and other underwater hazards.

RIB landing on beach

Here are some of the most beautiful bays and anchorages in the Caribbean

The following are some of the most beautiful and popular anchorages in the Caribbean that offer stunning natural beauty, exceptional snorkeling, and a peaceful and safe anchorage for yachts and sailors.

  1. The Baths, Virgin Gorda, British Virgin Islands: This geological wonder is famous for its huge granite boulders forming sheltered sea pools and caves, providing an unforgettable swimming and snorkeling experience.
  2. Marigot Bay, St. Lucia: Surrounded by lush hillsides, Marigot Bay is a tranquil and picturesque location that offers a safe anchorage popular with yachts and sailors.
  3. Tobago Cays, St. Vincent and the Grenadines: This group of five uninhabited islands surrounded by a horseshoe reef, offers crystal clear waters, exceptional snorkelling and scuba diving, and the chance to swim with turtles, making it a quintessential Caribbean anchorage for nature lovers.
  4. English Harbour, Antigua: Home to Nelson’s Dockyard, a UNESCO World Heritage site, English Harbour is famous for its rich history, protected waters, and vibrant yachting scene.
  5. Anse de Colombier, St. Barthélemy: Accessible only by boat or foot, this secluded bay offers pristine waters and peaceful surroundings, making it a perfect anchorage for those seeking tranquility and natural beauty.
  6. Chatham Bay, Union Island, St. Vincent and the Grenadines: This remote and peaceful anchorage is ideal for snorkeling, swimming, and enjoying stunning sunsets, and its unspoiled nature makes it a hidden gem in the Caribbean.
  7. White Bay, Jost Van Dyke, British Virgin Islands: This picturesque anchorage is famous for its powdery white sand beach and turquoise waters, and is home to the famous Soggy Dollar Bar, where the Painkiller cocktail was invented.
  8. Norman Island, British Virgin Islands: Reputed inspiration for Stevenson’s “Treasure Island”
  9. Deshaies, Guadeloupe: A charming anchorage set in a beautiful bay, Deshaies offers a quaint town vibe with colorful buildings, botanical gardens, and excellent dining options, providing a perfect blend of natural beauty and local culture.
  10. Salt Whistle Bay, Mayreau, St. Vincent and the Grenadines: This half-moon bay with its stunning beach offers a tranquil anchorage and is a perfect spot for relaxation, and is a popular stop for yachts cruising the Grenadines.
Caribbean beach anchorage

How much does sailing in the Caribbean cost?

Planning a sailing trip in the Caribbean? The cost can vary significantly based on multiple factors such as the type of charter, boat size, season, and the islands you intend to visit. To give you a rough idea, here’s a breakdown:

For bareboat charter (rental-only), you can expect to pay anywhere from $2,000 to $10,000+ per week, depending on the boat size, model, and age. Catamarans are generally more expensive than monohulls due to their space and stability.

If you opt for a crewed charter (which includes captain and crew), the cost starts at around $10,000 per week and can go up to $50,000 or more for luxury yachts. However, this cost typically doesn’t include provisions and fuel.

There are also additional costs to consider, such as food and provisions (budget around $25 to $50 per person per day if you plan to cook on the boat), fuel and water (which can vary depending on your sailing distance and boat type), mooring fees and marinas (fees range from $30 to $100+ per night), insurance (charter companies often require damage waiver or insurance which can cost a few hundred dollars), transportation (including flights to the Caribbean and transfers), and customs and immigration fees (budget under $100 in most cases).

Rubicon 3 sailing trips in the Caribbean provide amazing value for money, with the price per person around the $2900 mark. If you’re looking to save or travelling solo, this is a brilliant way to do so.

Indian River Dominica

The best islands to explore in the Caribbean

So by now, you’ll be in no doubt that the Caribbean is a true paradise for sailors, with its azure waters, lush landscapes, and vibrant culture. Among the many islands, St. Lucia, Dominica, Antigua, Cuba, Jamaica, The Grenadines, and The Bahamas stand out as some of the very best destinations for those seeking a unique sailing experience. Here’s why:

St. Lucia, famous for its dramatic landscapes and white sand beaches, is a must-visit for sailors seeking adventure and luxury. Anchor at Marigot Bay or Rodney Bay, and explore the towering Pitons, underwater coral reefs, and stunning scenery. It has a good marina and great flight connections.

Dominica, known as the “Nature Island,” offers a truly authentic and untouched experience ideal for eco-conscious sailors and nature enthusiasts. Anchor at Portsmouth or Prince Rupert Bay, and hike through lush rainforests, swim in waterfalls and hot springs, and enjoy the island’s commitment to conservation. We LOVE Dominica and it has to be one of the best Caribbean sailing destinations of all.


Antigua, a sailor’s paradise, boasts 365 beaches and excellent sheltered anchorages steeped in naval history. Anchor at English Harbour or Falmouth Harbour and take part in the Sailing Week, one of the premier yachting events globally.

Cuba, the largest Caribbean island, is a great sailing destination and offers a unique blend of cultural richness and historical intrigue. Anchor at Cienfuegos or Varadero, and explore the island’s unique culture, colonial architecture, pristine marine environments, hidden coves and beautiful beaches.

Jamaica, famous for its lively culture and reggae music, offers a mix of adventure and relaxation. Dock at Montego Bay or Port Antonio, and enjoy deep-sea fishing, diving, and waterfalls set amidst lush mountains.

The Grenadines, the chain of small, mostly uninhabited islands are part of the Windward Islands and offer secluded beaches, clear blue waters, and vibrant coral reefs. Anchor at Bequia, Mustique, or Tobago Cays, and immerse yourself in the Caribbean’s natural wonders. Grenada is nicknamed the spice island because of the ubiquitous nutmeg.

Swimming Pigs

The Bahamas, an archipelago of over 700 islands and cays, are one of the great Caribbean destinations and offer some of the clearest waters in the world. Anchor at The Exumas or The Abacos, and explore the Exuma Cays Land and Sea Park, the first protected marine area in the world.

San Blas Islands, are a pristine archipelago off the northern coast of the Isthmus of Panama, in the Caribbean Sea. Comprising around 365 islands and cays, of which only about 49 are inhabited, this idyllic destination is home to the indigenous Guna Yala people, who have maintained their autonomy and cultural heritage. The islands are renowned for their spectacular natural beauty, featuring crystal-clear waters, powdery white sand beaches, and vibrant coral reefs teeming with marine life.

Tropical fish
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