Best Places to Sail in the Caribbean

March 21, 2024 9 min

Are you dreaming of palm-tree-lined beaches, rum cocktails and turquoise waters? It’s time to book your next sailing vacation, and there’s no place better than the sensational Caribbean. Hot and sunny with a vibrant culture and delicious cuisine, what’s not to love?

As you begin planning your Caribbean yacht charter, you might be wondering about the best places to sail in the Caribbean. Of course, the best destinations to sail may change depending on several factors, such as:

Who you’re setting sail with (some islands may be perfect for families, while others are ideal for couples)
What time of year you want to visit (read about when the best time to sail in the Caribbean is)
Why you’re visiting the Caribbean (St Lucia is a romantic honeymoon destination, while the BVI offers some of the world’s best snorkelling opportunities)

Whether you’re planning a fast-paced Power charter, an all-inclusive crewed charter or taking the helm on a bareboat charter, this blog will take you on a journey around the best places to sail in the Caribbean, from Antigua to St Martin.

1. Antigua

Antigua english harbour — English Harbour from Shirley Heights

First on our list of the best sailing destinations in the Caribbean is Antigua. The rugged coastline, lush green hills, and vibrant coral reefs surrounding Antigua create a breathtaking backdrop for every sailing vacation, and we know you’ll fall in love with the island’s charm the second you set sail.

From pristine beaches to fun-filled sailing events, why is Antigua one of the best places to sail in the Caribbean for sailors of all experience levels?

Incredible sailing conditions – Much like our other Caribbean destinations, Antigua is world-renowned for its brilliant sailing conditions. With consistent trade winds, warm waters and low tidal ranges, you’ll find sailing a breeze in Antigua. Learn more about the fantastic cruising conditions in Antigua.
365 Beaches – Another reason why Antigua is one of the best sailing destinations in the Caribbean is because of its breathtaking beaches. With 365 beaches lining the shores of this beautiful island, Antigua is a true paradise if you want to soak up the sun.
Regattas – While the BVI is known as the sailing capital of the Caribbean, Antigua is known for being the regatta capital of the Caribbean. How did it earn this reputation? Every year, Antigua is home to world-class sailing events and races such as Antigua Sailing Week which draws in novice and experienced sailors alike.
Island Hopping – Antigua’s location among the Leeward Islands makes it a perfect starting point for exploring neighboring destinations like Barbuda, Guadeloupe, and St. Kitts and Nevis, each offering its own unique sailing experiences.

Looking for more inspiration? Take a look at our blog on the best things to do in Antigua, and view our Antigua Itinerary.
Does Antigua sound like the perfect place to relax, unwind and switch off from the world on a sailing vacation? All that’s left to do is find out the best time to set sail in the Caribbean, build a quote and book your sensational Antigua yacht charter today.

2. British Virgin Islands

Moorings 534PC Power Catamaran in the BVI

From the legendary sailing grounds of the Sir Francis Drake Channel to the natural beauty of The Baths, every sailing charter around the British Virgin Islands uncovers new treasures. Get ready to channel your inner adventurer as you chart your course around these stunning islands.

Why is the BVI one of the best places to sail in the Caribbean, and the whole world?

First time sailors – The BVI is universally known as being a fantastic sailing playground for first-time sailors because of its line-of-sight navigation, reliable trade winds and sheltered waters. Find out more about the sailing conditions in the BVI. Heading on your first ever yacht charter? Take a look at our top tips for your first BVI sailing vacation.
Island hopping – Similarly to Antigua, the BVI is also an incredible sailing destination if you want to explore a variety of islands. With over 50 islands, islets and cays making up the British Virgin Islands, you’ll find opportunities for exploration everywhere you turn. Some of the best islands to sail around in the Caribbean are part of the BVI, including Virgin Gorda and Jost Van Dyke.

Sailing events – The British Virgin Islands host prestigious sailing events such as the BVI Spring Regatta & Sailing Festival, attracting sailors and spectators from around the world to participate in exhilarating races and celebrate sailing.
Natural beauty – From the iconic Baths on Virgin Gorda to the stunning coral reefs of Anegada, the British Virgin Islands are blessed with breathtaking natural beauty both onshore and in the crystal clear waters that surround them.

Does the BVI sound like a Caribbean dream come true? Take a look at the best time to sail in the BVI and start planning your relaxing vacation today. We think Power yachts are one of the ways to experience the magic of the British Virgin Islands as they’re faster and more powerful than sailing yachts which means you can spend more time uncovering the wonders of Tortola, Anegada, Jost Van Dyke and Virgin Gorda. Find out more about the benefits of chartering a power catamaran.

3. Grenada

Next on our list of the best islands to sail around in the Caribbean is Grenada. With its rich sailing history and captivating charm, Grenada offers a slice of heaven for experienced sailors, families, couples and everyone in between.

From the iconic Grand Anse Beach to the unspoiled shores of Carriacou, why is Grenada one of the best places to sail in the Caribbean?

Brilliant cruising conditions – Grenada is unique in that its tropical climate allows for year-round sailing, giving you the freedom to choose what time of year you set sail on your sailing vacation. Surrounded by well-protected anchorages, Grenada offers a safe and serene sailing environment with countless opportunities for exploration. Learn more about the sailing conditions in Grenada.
Unforgettable diving and snorkeling – Grenada is known for its world-class diving and snorkeling spots. You can discover vibrant coral reefs and underwater sculptures, adding an extra layer of excitement to your sailing experience. Are you a thrill seeker looking for the adventure of a lifetime? Take a look at our blog on the best snorkeling spots in the Caribbean.
Culture – Nicknamed the ‘spice isle of the Caribbean’, Grenada offers a unique cultural experience with its spice gardens, traditional markets, and flavorful cuisine. You can explore the island’s rich history and indulge in the aromatic scents of nutmeg, cinnamon, and cloves…our mouths are watering already.
Sailing regattas – Grenada hosts various regattas and sailing events, such as the Grenada Sailing Festival and Grenada Sailing Week. These events offer the chance to immerse yourself in the local sailing community and take part in exciting races.

Find out more about what you could expect to get up to during your yacht charter by taking a look at our Grenada Itinerary. Can’t wait to explore the beauty of Grenada? Build a quote and book your sailing vacation today.

4. St Lucia

With its towering Piton peaks, lush rainforests, and pristine beaches, St Lucia is a true sailing wonderland. Picture yourself gliding around the island’s coastline as you discover secluded coves and secret bays, what more could you ask for?

Why is St Lucia one of the best sailing destinations in the Caribbean?

The Pitons – We couldn’t write a piece about the best places to sail in the Caribbean without mentioning the iconic Piton peaks that rise majestically from the sea in St Lucia. These beautiful, towering mountains are a testament to the incredible natural beauty you’ll experience when you sail around St Lucia. Did you know…you can even snorkel around the base of Gros Piton? Find out more by checking out our St Lucia Sailing Itinerary.
Gorgeous beaches – St Lucia is home to some of the world’s most picturesque beaches with powdery white sand and crystal-clear waters, perfect for mooring up and enjoying a day of swimming, sunbathing, and switching off from the world. Our favorite beaches in St Lucia include Anse Mamin Beach and Anse Cochon Beach. Find out more about the best beaches in the Caribbean.
Exotic marine life – The waters surrounding St Lucia are teeming with vibrant marine life, making it a paradise for snorkelers and divers. Some of our favorite diving spots include the Wreck of the Lesleen M and the Key Hole Pinnacles, where you’ll come face to face with an abundance of marine life, such as golden-spotted eels, pufferfish and stingrays.
Sensational sunsets – The ultimate honeymoon destination, St Lucia is renowned for its magical sunsets that paint the sky in shades of orange and pink every evening. Whether you watch them from the deck of your yacht, one of the island’s stunning beaches or an outdoor restaurant, we know you’ll fall in love with the charming sunsets of St Lucia.

Find out more about why St Lucia is one of the best bareboat charter destinations in the world, alongside the likes of the BVI and St Martin. Whether you’re setting sail on a romantic honeymoon or simply want to experience the beauty of St Lucia on your next vacation, we can’t wait to welcome you aboard one of our world-class yachts in St Lucia. Build a quote and book your charter today.

5. St Martin

Whether you’re a seasoned sailor searching for an exhilarating cruising ground or a first-time sailor wanting to learn the ropes, St Martin is a dream come true for all sailors. From its fantastic blend of Dutch and French cultures to its calm waters and breathtaking landscapes, we love St Martin and know you will too.

Why is St Martin one of the best islands to sail around in the Caribbean?

Culture – St Martin is divided between French and Dutch territories, providing a diverse cultural experience and allowing sailors to explore two distinct sides of the island with unique atmospheres, cuisine, and attractions.
Natural beauty – Another reason why St Martin is one of the best places to sail in the Caribbean is because of its sensational natural beauty. St Martin enjoys the best of both worlds, with exceptional scenery on land and in the open waters. From lush green hills to colorful coral reefs, there’s no end to the island’s charm.
Watersports – When you’re not cruising on the water, you’ll want to be spending time in it when you visit St Martin. During your charter, you can look forward to snorkeling, scuba diving, swimming, paddleboarding and so much more. The Creole Rock is one of the most popular spots for snorkeling in St Martin, and also makes a great starting point for beginner scuba divers.
Island Hopping – Similar to Antigua, St Martin’s fantastic location means you can easily island hop around other Leeward Islands, such as St Barts and Anguilla. Take a look at our St Martin Sailing Itinerary to learn more about where you can explore during your relaxing yacht charter.

One of the cultural hotspots of the Caribbean, there is truly no other island like St Martin. Build a quote and start planning your blissful sailing charter today. Will you take the helm on an adventurous bareboat charter, hire a skipper so you can focus on admiring the views of St Martin, or book an all-inclusive crewed charter where you’ll be given the five-star treatment by our crew of skippers, chefs and housekeepers?

6. St Thomas

The last destination on our list of the best places to sail in the Caribbean has to be the gorgeous islands of St Thomas and the USVI. Home to secluded coves, crystal clear waters and some of the best shopping in the Caribbean, St Thomas is a wonderful destination for a sailing vacation.

Why is St Thomas one of the best places to sail in the Caribbean?

Smooth sailing conditions – St Thomas is a sailing haven for experienced and novice sailors alike. With calm waters, average temperatures of 75°F and 88°F and the iconic Christmas Winds producing up to 30 knots of wind, St Thomas is the ultimate cruising ground. Find out more about the sailing conditions in St Thomas.
Historic sites – Are you looking for a sailing destination in the Caribbean with historical and cultural importance? St Thomas has a wide range of incredible historical landmarks, including Blackbeard’s Castle and Fort Christian.
Stunning beaches – Another reason why St Thomas is one of the best places to sail in the Caribbean is because of how many exquisite beaches there are just waiting to be discovered by you. Some of our favorites include Lindqvist Beach, Sapphire Beach and Brewer’s Bay.
Location – St Thomas sits in one of the best locations in the Caribbean, with easy access to the rest of the US Virgin Islands and the British Virgin Islands. In a matter of days, you can explore the likes of St John, St Croix, Tortola, and Anegada. Each island has something different to offer, from beautiful beaches to sensational restaurants and friendly local communities. Take a look at our St Thomas Sailing Itinerary to learn more about the amazing islands you could sail around during your charter.

Can you picture yourself relaxing on the sandy beaches of St Thomas before setting sail to explore one of the nearby islands? Build a quote and book your yacht charter today. Still choosing the best place to sail in the Caribbean and need more inspiration? Check out our blog on the best things to do in the Caribbean.

Book your Caribbean yacht charter today

So there you have it, the best places to sail in the Caribbean. Want more inspiration before choosing your next Caribbean vacation destination? Take a look at our base pages and find out more about the wonders you’ll uncover when you explore them:

Whether you’re booking a Power yacht charter in the BVI or a crewed charter in Grenada, we can’t wait to welcome you aboard one of our Power yachts or Sailing yachts soon. If you have any questions about the best places to sail in the Caribbean, please get in touch with us today.