Yacht Charter Caribbean

Explore Paradise on Earth

Why a Yacht Charter in the Caribbean?

Haunt of buccaneering pirates, these magnificent islands have been squabbled over by the French, Dutch, English and Spanish, these islands in the Caribbean Sea hold a Special allure to those who count Robert Louis Stephenson’s Treasure Island among their favourite books. This dark and troubled history has only served to enhance the romance that surrounds them.

For sometime the Caribbean has been the charter destination, a playground that promises steady trade winds, warm seas, sparkling colours and, of course, as many variations of rum punch as there are beachside bar tenders to mix them. Yet there is more than enough adventure for those seeking to get way from the crowd too, try Castro’s Cuba before it’s too late.

List of 6 Places To Visit in The Caribbean

Where to sail?

In the Caribbean, the dry season is from February to June, delivering only an occasional rain shower. From July to January, the wet season brings frequent showers with lots of sunshine and the occasional rainy day. Expect 26 to 30 Celsius degrees  with balmy winds all year round. Squalls produce intense rains and sometimes winds in excess of 40 knots. The winter months, November to March, produce strong Christmas winds. During this time, storms from the north produce swells and may create an unsafe anchorage, so be prepared to move to a safer location. In June, the winds diminish and clock to the southeast at 10 to 15 knots.


The British Virgin Islands  are rated as one of the world’s top cruising destinations. Along with some superb sailing and idyllic protected anchorages a yacht charter, flotilla vacation or sailing schools course in the BVI guarantees as much fun as you can handle – it’s the destination of choice for those who like a party as much as they like to sail.

The St Martin area offers a terrific blend of easy island-hopping and more challenging open-water passages in a truly stunning location. With Dutch and French influences being combined easily with the local Caribbean culture and the island’s reputation as the ideal place to throw a good party, you can be assured of some excellent food and great live music wherever you end up.

Whilst cruising the St Maarten sailing area, be sure to make a visit to Grand Case, also called the ‘Dining Capital of the Caribbean’! With numerous excellent restaurants to choose from, in Grand Case you can enjoy lunch or dinner right on the beach and enjoy the beautiful views and sunsets.

Another anchorage you should be sure to visit is Tintamarre. This island is just off the North-East coast of the French Side of St Maarten and is ideal for a beach-hangout. Tintamarre is perfect as a lunch stop or to do some snorkeling. Enjoy exploring the island or just relaxing on one of the best beaches we have. This anchorage is only accessible by boat so it rarely gets crowded – enjoy Tintamarre!

The Bahamas area offers easy island-hopping from one deserted beach to the next in crystal clear waters. Start your trip from Abaco and explore this fantastic place. An ideal choice for families and less experienced sailors, the sheltered cruising grounds of the Sea of Abaco are perfect for those who want to take life easy and enjoy a relaxed sailing vacation in the Bahamas.

Nassau & Paradise Island are great places to start your sailing trip, as you’ll find full-service marinas with electrical hook-ups, fuel, Internet connections and accommodation. The ideal period to visit the area is from December to May or June. From July to October, most of the bars and restaurants are closed due to the Hurricane Season.

The Antigua offers the perfect choice if you’re looking to mix the Caribbean party lifestyle with great sailing conditions and stunning white sand beaches (365 to be exact, one for each day of the year!). With warm, steady trade winds and so many idyllic safe harbors, Antigua is a fantastic Caribbean yacht charter destination.

This very special cruising ground offers some of the best coastal sailing and passage making you will experience. With a perfect climate of 27 degrees year round, the breeze is always easterly around 15 – 20 knots in high season; perfect conditions for couples, families and groups alike on your Antigua yacht charter.

Antigua is famous for having hundreds of white sand beaches and turquoise waters. If you are looking for an unspoilt charter paradise, you’ve found it here. The north of Antigua is protected by a cluster of tiny offshore islands which are perfect snorkeling spots. Green Island to the east offers the best spot for kite-boarding and paddle boarding.

St Vincent and the Grenadines offers great balance for those looking for a little more sailing that the British Virgin Islands offers, which still enjoying the wonderful warmth of the Caribbean people. It can be combined with a visit to Grenada and St Lucia if time allows it.

Only 9 of the 32 islands are populated. From St. Vincent’s lush tropical rainforest full of eco-adventures, to the idyllic beaches, coral reefs and turquoise lagoons of The Grenadines, SVG is a tropical paradise for yachting, scuba diving, enjoying nature, and relaxing in luxurious hideaways.

Grenada, “The Spice Island of the Caribbean”; a rolling, mountainous island, abundant with wildlife, sea life and plant life.  The island offers a world of itinerary options for sailors who are a bit more experienced and is the perfect placed to start your sailing vacation in the Windward Islands. Ideal for one way trips to St. Vincent.

St Lucia; the Jewel of the Windwards. Offering stunning views, picturesque harbours, lush rainforest and a spectacular dormant volcano you can actually venture inside, a sailing vacation here is the perfect place to begin your exploration of the beauty and riches the Caribbean has to offer.

Cuba is like a prince in a poor man’s coat. Travel to Cuba can be an exhilarating roller-coaster ride with rich history, intoxicating atmosphere and crumbling, but magnificent architecture. Particularly stirring in the Unesco-listed cities – Havana, Trinidad, Cienfuegos and Camagüey – where grandiose squares and cobbled streets tell erstwhile tales of opulence and intrigue.

The best area for sailing is around –  the Jardines de Reina, María la Gorda and the Isla de la Juventud – are all fairly isolated, making this adventure even more exciting. The turquoise waters are ideal for sailing – preferably on a cat – and exploring this area’s exquisite hidden beauty.

Bareboat Yacht Charter Caribbean

If you already have a valid qualification, you can easily bareboat charter in the Caribbean, as your experience will be enough to validate. Even if you only have your qualification for a few months, you are able to sail without any assistance. Sometimes, the operators require a minimum level of experience, even if you do have your license.  In this case, they can provide you with a free member of their crew for just a few hours, in order to show you the basics and ensure that you can handle the yacht yourself.

With numerous certified partners that are ready to offer you access to their great fleets, we are more than certain that we will find the perfect bareboat charter for you in the Caribbean. You can learn more about how the bareboat charter works here. You can send us your request either by sending an email to info@sailchecker.com or leave your enquiry here. An experienced Yacht Charter Consultant will be in touch shortly.

Crewed Yacht Charter Caribbean

Do you want to sail in the Caribbean, but you don’t have the essential qualification? No worries – we can find you the perfect crewed charter. We can simply add a skipper that will be with you and sail the yacht in the areas. You can prepare an itinerary yourself or compile your ideas with the ones of your knowledgeable captain hence creating the perfect route.

What’s more, we can even add a hostess or a chef to take care of the yacht and prepare the meals and drinks for you, while you enjoy the trip. Many people think that the crew can be hired only on luxury yachts; this is not true. You can choose the yacht of your liking, that perfectly meets your criteria and simply request for the crew.

You can learn more about the crewed yacht charter and how it works here. You can send us your request either by sending an email to info@sailchecker.com or leave your enquiry here. An experienced Yacht Charter Consultant will be in touch shortly.

Offers – Yacht Charter Caribbean

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