Top 5 best places to sail in the Caribbean Sea—including the top ports, their conditions, and prices per day

best places to sail in the Caribbean Sea
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With its deep blue seas and white beaches, the Caribbean Sea and its thousands of islands, is nothing short of paradise on earth. Cruising between these islands, taking in the sunlight, listening to the birds, and eating colorful foods produced in local markets are all reasons why you should put the Caribbean Sea high on your destinations list.

With 7,000 islands, divided by endless cultures and beaches to visit, how could this not have something for you? Find the incredible colors of fish and coral underwater or catch the perfect wave on the surface. Find yourself immersed in centuries-old cultures, with your toes in the sand of the many impeccable beaches while enjoying joy-inducing music. The Caribbean really offers it all!

When it comes to weather, the Caribbean is known for offering the most sought-after climate on the planet. Temperatures generally fluctuate between 75-85°F (24-29°C), rarely cold and never too hot. Plus, only a reasonable amount of rainfall year-round. The best time to visit would be from December to April when it's a little cooler, drier, and less humid than the rest of the year. This would be a great time to escape the colder winter months up north. Though, really, the best time to visit the Caribbean sea depends on your interests.

To visit the Caribbean from the U.S. has its advantages. It's a paradise so close to home, while still being incredibly different in its beauty, cultural diversity, and vibrance. It's the perfect place to get rest and find that flawless boating experience. Did we mention several locations don't require visas?

In this article, we will talk about five ideal destinations for your boat trip. We will mention the port amenities and the best time of year to visit the island. We'll also round up the size of ports, prices, and distances between the islands. With 7,000 to choose from, we won't be able to mention all of them of course. The only way to find out which islands are your dreamiest, you'll just have to go and explore the Caribbean yourself. Ready to take the plunge into paradise? Let's go! 😎

The destinations

Cayman Islands

cayman island sailboat

Made up of three individual islands, the Cayman Islands offer miles of sandy white beaches, as well as the best diving spots. No matter what you're looking for, the Cayman Islands have it. A beautiful melting pot of cultures and nature, the Cayman Islands are a place worth visiting. Plus, U.S. citizens don't need a visa to visit the three idyllic islands making this boat trip hassle-free.

Besides having the finest beaches and clearest waters, the Cayman Islands are also known for their stingrays. You can visit Stingray City, a group of sandbars where you can walk between these magnificent fish. Other places to visit include George Town, the splendid capital, the Cayman Turtle Center, where you'll be able to join the Cayman Island's famous old residents, and the Crystal Caves, filled with beautiful stalactites and stalagmites.

The Cayman Islands offers harbors and marinas on their biggest island (Grand Cayman) and harbors, but no marinas on the second biggest island of the three (Cayman Brac). The biggest marina, the environmentally friendly Barcadere Marina, offers 85 slips and includes all facilities necessary for your stay. The rates differ depending on the amount of time you'd like to stay at the marina. Daily rates go from 1.80 U.S. dollars per-feet per day to 1.20 U.S. dollars per-feet per day if you're staying for more than four weeks. Plenty of reason to plan a long stay!

Saint Lucia

saint lucia sailboat

Saint Lucia is a clear melting pot of English, French, and Dutch influences. In the 1600s they all descended on the island in hopes of setting up a New World. The strong heritage and cultural identity that belong to the island are still vibrantly celebrated by locals. The history of piracy and colonialism have left their marks too, but that doesn't take away the breathtaking views and unstoppable optimism of the Saint Lucians.

The island is rich with mountains, jungles, beaches, and historic sites that tell the winding history of Saint Lucia. An unmissable landmark is the Pitons, two volcanic plugs that inspire many visitors and climbers to travel to this island. You can walk around them and see the many beautiful flora and fauna native to Saint Lucia. Another famous landmark on Saint Lucia is the town of Soufrière, named after the sulfurous aromas coming from the volcanoes. The best way to discover the island of Saint Lucia is to ask the locals. They are super welcoming and happy to tell you their favorite hiking trails, beaches, or nightclubs.

According to Oprah Winfrey, Saint Lucia is one the top five places to visit and since U.S. passport holders do not need a visa to visit Saint Lucia, planning a trip here is fairly easy. The island has multiple harbors and a marina next to the capital city of Castries. The Marigot Bay Marina, proclaim themselves as the most secure anchoring spot in the Caribbean. The Marina has 42 slips and has all the amenities needed to make your stay worth the visit.

Antigua and Barbuda

antigua and barbuda sailbaot

The two tropical islands of Antigua and Barbuda are in the heart of the Caribbean Sea. Although 28 miles apart, the two islands together form a nation, part of the Commonwealth. Antigua was born more than 30 million years out of a volcano. Reefs started forming on this volcano and now the greater part of Antigua is low-lying and composed of lime rock. The majority of the population (80,000 people) live on Antigua. Barbuda, on the other hand, is less populated with 1,200 people living on the island.

The islands are famous for their beautiful sunsets and gorgeous views, but that's not all they have to offer. The famous Fig Tree Drive takes you through banana trees (locally called 'figs'), mango trees, and rainforest teeming. Another famous landmark is Boggy Peak, famously named Mount Obama between 2009 and 2016 to honor the 44th U.S. President Barack Obama. Lastly, for snorkeling and diving fanatics, Cades Reef offers amazing views of the reefs, sunken wrecks, and beautiful caves. This place shouldn't be overlooked if you're a snorkeling fan.

If this hasn't made up your mind to visit Antigua and Barbuda, maybe the visa requirements will. For U.S. citizens, no visa is needed as long as you have proof of a plan to return to the U.S. Both Antigua and Barbuda offer marinas and harbors, both having plenty of slips available. One of the famous marinas is AYC Marina & Resort. This marina offers slips for different boat sizes. Prices differ from $2 per-feet per day for small-sized boats to $2.50 per-feet per day for bigger vessels.


St Brth sailboat

This tiny Caribbean island has endless possibilities for shopping, beach-going, eating, and drinking. St Barth (as the locals call it), has a well-documented reputation for glamour and is commonly known as a seaside sanctuary. Many visitors come to relax on the white beaches, having their toes in the sand while having lunch or dinner in a pristine restaurant–with a bottle of the finest French wine. Known as the Caribbean's culinary capital, the island offers world-class dining and every season foodies flock to St Barth for newly open restaurants and to have a private chef serve dinner. And we haven't even talked about the shopping...

St Barth lays in the northeastern corner of the Caribbean, only 15 miles away from Saint Martin. The island, with its eight square miles, is small even for Caribbean standards. Its serpentine roads are characteristic of the volcanic disruption that created the island some 50 million years ago.

Many people visit St Barth because of its strong maritime history. The St Barth Bucket Regatta is one of the most famous regattas. The international regatta attracts thousands of people every year and has been held for 36 years. Another one is the famous Les Voiles de St Barth Richard Mille, a five-day racing event that focuses on eco-friendly racing. (Interested in eco-boats? Check out our selection.)

The Gustavia Port Marina is a perfect place to moor your boat as it's completely surrounded by St Barth's capital Gustavia, making it easily accessible for day trips around the island. The fees to moor at Gustavia Port are surprisingly cheap. The prices differ from $0.25 per-feet per day to $0.50 per-feet per day. And you guessed it: no visas are required for U.S. passport holders—making the trip even more pleasant.


Martinique sailboat

With an active volcano and two mountains on a relatively small piece of land, the island of Martinique is hilly, to say the least. Martinique offers it all; from high culinary delights to famous hiking trails, from waterfalls to the best rums of the Caribbean Sea.

The island uses the euro, flies the French flag, and has French as its official language, but its character, food, and musical heritage lean a lot more towards their Afro-Caribbean roots. The famous Martinican gastronomy combines the highlights of French cuisine, Indian spices, and African generosity. The dishes made in one of Martinique's 375+ restaurants show the generosity and cheerfulness the Martinicans have to offer. Besides its food, Martinique offers award-winning rums that will make all the rums you've tasted before disappear in vain. Dubbed the rum-capital of the world, the island is home to 12 different brands, each unique in their own way.

It's not only food and drinks Martinique has to offer. The island's majority is still covered in rainforest with beautiful hiking trails along the coast and mountain ranges. If you add the beautiful diving spots and white sand beaches to this equation, you have an ultimate get-away island, in the middle of the Caribbean Sea.

And that's not all. U.S. citizens are allowed to stay on the island for three months without needing a visa, although a passport is necessary. Besides this, Martinique offers many marinas to moor your boat. You'll need it, because this island is in dire need to be explored.

So there you have it. We've talked about some of the amazing islands in the Caribbean sea. We're aware there are many more islands in the Caribbean Sea that deserve a mention, and that this is only a small part of the islands worth visiting. The Caribbean Sea has so much to offer for boating that it makes us wonder why we're not there yet: the turquoise water, white sandy beaches, bright green rainforests, never-ending sunny days, culinary treasures, tastiest cocktails. There's an abundance of reasons to visit these islands and each and every one has its own hidden gems.

When you decide to visit, be sure to tag us in your photos on your favorite spots, restaurants, ports or beaches.

If you're looking for your own vessel to take with you on this trip, be sure to check out BOATIM and find your future boat! 🚤

Disclaimer: With COVID-19 restricting the travel possibilities, make sure to visit governmental websites to find out if you're allowed to travel to your destinations.

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