Yacht Charter Caribbean

Book your Caribbean yacht charter with Borrow a Boat and enjoy sailing in this tropical paradise that has little competition in terms of a yacht charter vacation.

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Yacht Charter Caribbean

Book your Caribbean yacht charter with Borrow a Boat and enjoy sailing in this tropical paradise that has little competition in terms of a yacht charter vacation.

Comprising of 7,000 islands stretching 2,500 miles south from Florida to Venezuela, the islands are as rich and varied in culture and things to do as any sailing destination in the world. Perfect for a winter sun holiday, their steady winds and year round warmth make for one of the best holiday spots you will ever enjoy.

The Caribbean island group was inhabited for thousands of years by different civilisations of what we know as the Arawaks. The arrival of Christopher Columbus in 1492 changed that, and in many cases changing hands between European empires several times, they become centres of production of sugar and salt for nearly 500 years.

As the US gained in strength and the European empires fell, so today many are independent, while others remain under the protection of their old masters. This can mean a lot of stamps in your passport on even a week or two's sailing holiday. However, despite the bureaucracy they have still benefitted from their sun, sea, sand, reefs and beaches as major draws to their lands.

Wherever you go on a yacht charter Caribbean you will find a white sand beach to lie on, a coral reef to dive on, excellent, steady winds to enjoy water sports with, and a wide array of fun to be had ashore.

With Borrow A Boat you have a chance to get a taste of all this and more. Book your yacht charter vacation with us today!

Hiring A Yacht In the Caribbean

Whether planning a bareboat charter or crewed luxury yacht charter in the Caribbean, you will be spoiled for choice as to the activities you can enjoy. The sailing and diving is world class wherever you go, with the trade winds and beautiful reefs offering much on your sailing holiday.

As we will explain later, some islands such as St Maarten and St Thomas in the Lesser Antilles are very developed with a wide range of boutiques, restaurants and hotels to choose from. Others such as Cayman Brac and the Exuma Sea Park are almost forgotten as far as structured activities are concerned but no less beautiful and relaxed. There are beach bars with infamous reputations (BVI has a few, though you don't have to look far!) and family oriented fun on sandy beaches or in the sea can be enjoyed almost everywhere.

You can turn up to one of the many sailing events such as Antigua Sailing Week in the first week of May every year. You can either crew or charter a luxury yacht all to yourself to compete in one of these top end sailing regattas with some of the most beautiful yachts ever built competing.

Whatever you want from a yacht charter, the Caribbean probably has it. Read on to find out more about the islands and what you might enjoy on a Caribbean yacht charter.

Getting to the Caribbean

Not all islands (or even countries) in the Caribbean have international airports, though many will have regional airports connected to international hubs elsewhere. Here are a few hubs from which you can get to your charter yacht elsewhere in the region.

Miami Airport

Miami is a major international airport with flights direct from Europe, the Americas and much of the rest of the world. You can connect to islands in the Bahamas, Lesser Antilles, Jamaica Cayman Islands, Jamaica and Cuba.

St Maarten

Princess Juliana International Airport is a hub for the Leeward Island group, and is closer to the Virgin Islands than Miami for ferries and onward flights.


Jamaica has three international airports in Kingston, Montego Bay and Ocho Rios.


Jose Marti International Airport in Havana is the only one on the island. For a Cuba yacht charter, this will mean a 2-3 hour bus ride to the marina.


Grantley Adams international Airport is the major international hub for the eastern Caribbean.

Best Areas To Charter in the Caribbean

There are three main areas in which to enjoy your dream yacht charter with Borrow a Boat. There many countries and international borders within these too, so these are largely broken down by geography.

Bahamas and Turks & Caicos Islands

The smaller islands between Florida and Cuba/Hispaniola, these are just two countries but consist of hundreds of islands and cays.

The Bahamas are centred on Nassau and from here you can enjoy the northern Bahamas with their British colonial flair or the southern Bahamas around Exuma Sea Park with its protected land and waters.

The Turks & Caicos Islands (TCI) centred on Grand Turk are 40 islands and cays with world class diving and ashore, world class shopping and entertainment.

Greater Antilles

Including the Cayman Islands, these are primarily the larger islands of Cuba, Jamaica, and Hispaniola (Dominican Republic/Haiti).

Jamaica has a reputation all of its own with its unique and free living culture. Montego Bay has its own airport and is a major yacht charter destination.

Cuba has a fast growing yacht charter industry, centred on Cienfuegos on the south coast. Out of Cienfuegos you can bareboat charter or get a skippered yacht charter to the cays and islands to the south.

The Cayman Islands are two halves: Grand Cayman is a cosmopolitan international finance centre with top end bars, restaurants and boutiques, while the two smaller islands are more quiet, paradise islands.

Lesser Antilles

With Puerto Rico at the top, these stretch in a curve for a good thousand miles to just off the coast of Venezuela and Belize.

Comprising of more than 1000 islands and cays, these in turn are split into two:

The Leeward Island group to the north include the three Virgin Island groups, Anguilla, St Maarten, Antigua & Barbuda, St Kitts & Nevis and Montserrat.

The Windward Island group to the south and east include Guadeloupe, St Lucia, St Vincent and the Grenadines, as well as Barbados, Martinique, Trinidad & Tobago.

Best Islands To Charter A Yacht In the Caribbean

With the island chain so long, there are of course certain centres for you to enjoy your Caribbean yacht charter. Based on the three regions above, let's look at some highlights.


Nassau is the main hub in the Bahamas. From here you can either fly to or sail to the charter base and sail from there. The three main areas are the Berry Islands (notable for their fishing), Abaco Islands (golf, spas and colonial towns) and Exuma (protected land and sea wilderness).

Turks & Caicos Islands

Among the 40 islands, Grand Turk is the cosmpolitan centre and main base for your sailing vacation. Scuba divers and free divers flock here for the 700 metre deep waters off the nearby continental shelf.

Greater Antilles

Cuba is a fast growing and under-appreciated island for chartering a yacht. Much of the industry is based in Cienfuegos on the south coast, and you can visit different cays on your holiday.

Jamaica is another jewel in the Caribbean Sea with its lush forests, mountains and idiosyncratic subcultures. Montego Bay is the main centre here.

The Cayman Islands are another important charter base. Grand Cayman is a major cosmopolitan centre thanks to its banking and insurance industries. For those who want to drop after they have shopped, head to Little Cayman or Cayman Brac!

Leeward Island Group

The US Virgin Island archipelago is very developed and have their own international airport. St Thomas, St John and St Croix all have their draws from laid back beach bars to full throttle city fun.

To the north of USVI is the British Virgin Island group (BVI) that has no international airport but does have a reputation for wicked parties and beach bars. Tortola is the most 'developed' with marinas, towns and shops, as well as the Little Sisters to the south (including Norman Island, Peter Island and Salt Island). If you're down that way, head for Virgin Gorda and Jost van Dyke as these are well worth a visit!

Heading SE, you have St Maarten in Anguilla, one of the most tourism oriented islands in the whole of the Caribbean. To escape the madness, head over the border to St Martin, the less developed French side of the border!

Antigua and Barbuda are famed sailing centres - Nelson's Dockyard is one of those places so beautiful it will never leave you.

Windward Island Group

Guadeloupe, Dominica and Martinique are still part of France and have their very French twist to local culture.

South again, and you hit St Lucia, and newly independent from the UK, Barbados has the main airport for this part of the Caribbean. Both are noted for their beautiful white sandy beaches and scenery.

St Vincent and the Grenadines are some of the furthest south before you hit Venezuela. Do consider hitting the Tobago Cays to the south of here too - the diving is quite special.

Types Of Yachts To Hire

Where it comes to chartering you can hire a motor cruiser, a monohull sailing yacht or a catamaran. Each have their benefits. Let's take a look at highlights from the three regions above.

Sailing Yacht (Sailboat)

From US $100 or so a day up to whatever you can afford, monohull sailing yachts are fun to sail at all points of the wind, whether nose into a building sea breeze or blasting under all canvas downwind. A luxury yacht charter at an affordable price!


Far more luxurious than a sailboat these often have en suite toilets and showers in the staterooms as well as ample entertaining space in the saloon and on deck. They have twin engines to compensate for their lack of windward ability but are great sailing with wind abaft the beam.

Luxury Yachts and Superyachts

Want your own personal cruise ship for you and your group to leave the world behind? A luxury yacht in the Caribbean with crew to look after you from breakfast to bedtime could be just the ticket. Often carrying scuba diving equipment and in some cases even a diving guide, you can get the very best from a sailing vacation in the Caribbean in this way.

Motor boat

Whether a motor yacht with cabins or a day boat for a fishing trip / blasting up the bay, these are comfortable seagoing boats with a kick of speed should you want to cover a bigger distance on the day or just for the fun of having a 10 metre wide wake and 10 tons of steel flying along at 30 knots!


Very much day boats for fishing and day cruising, RIBs are a lot of fun for a day afloat. They can be very quick and are great should you be in a town on holiday and fancy seeing the coast or finding secluded white sand beaches from another perspective.

Skippered Yacht Charter or Bareboat?

Where it comes to a yacht charter in the Caribbean you have two choices - bareboat charter or skippered yacht charter. Both have their own advantages.

Skippered charter in the Caribbean

Fancy going on a sailing trip yet have no sailing qualifications or lack the confidence to go it alone? A skippered yacht charter gives you the advantage of being able to get afloat without having had to invest in getting sailing qualifications beforehand. You will pay over $100 a day extra for the skipper, as well as their food and a tip at the end but they will show you the best that the area has to offer with their local knowledge.

You will also be able to explore further afield than the traditional cruising grounds of bareboat sailing vacations.

Bareboat yacht charter in the Caribbean

For those who seek a bit of adventure off their own back without the expense of a paid skipper aboard, a bareboatcharter could be just the ticket. You will need sailing qualifications but for that you get to be the author of your own story afloat as you explore the coast and islands of Belize.

Do you need a licence to charter in the Caribbean?

If you want to bareboat charter you will need an approved boating qualification. Below is a list of relevant qualifications:

ASA 104 Bareboat sailing certificate: The American Sailing Association skipper minimum qualification for hiring bareboat yachts. BoatUS and US Sailing also offer bareboat charter qualifications, as does CANsail.

RYA: The Royal Yachting Association's qualifications (minimum Day Skipper level) is necessary for bareboat charterhire, it's also worthwhile seeing do you need to have done a VHF radio course as well as some boatowners will require this.

There are also many other European national boating qualifications that are accepted here too, it's worthwhile checking these details before hiring.

If you want a skippered boat rental as a charter yacht then you don't need any sailing certification at all, you just turn up and off you go.

Best Times To Hire

Unlike Europe, the sailing season in the Caribbean runs from November to May - perfect for a dose of winter sun. The NE Trades are settled and you will encounter weather between 25-35 degrees C.

Within this period, March and April after the winter northerlies have passed are cooler yet the sailing is just as fun as the rest of the year. Belize is after all a tropical country!

For those who want to try something a little outside their comfort zone, August and September are said to be the very best sailing months of all.

There's a problem with this - many yacht charter fleets will not be in the area thanks to hurricane season that runs between July and October. If booked and a hurricane is on its way your holiday will be cancelled. There is no minimising the danger of being in the region in a hurricane - there is no high ground and with the general trend for ever fiercer storms, it is not an experience to even risk being around for.

The Climate

North East Trade Winds: Similar to those of the Canary Islands these are regular and can get up to F6 at times, but steady and predictable.

May to November is hurricane season, and while the sailing can be fun it can be dangerous. With climate change as it is, hurricanes have increased in ferocity and frequency, and it really isn't worth the risk.

How much does it cost for a Carribean Yacht Charter?

There's almost a yacht for every budget when it comes to chartering. For US $120 a day - $840 a week - you can take a sailboat monohull out with five other adults. That is going to be cheaper than a week in a hotel for everyone.

Catamarans cost a lot more - expect to pay anything from $500 to $2,000 a day depending on the season.

Motor boats taken on a bareboat basis can cost as little as $500 a day if they have sleeping acommodation - much less if they are day boats.

RIBs can cost as little as $50 for an afternoon.

In each of the examples above you can take on a skipper starting at $150 a day depending on what the vessel is and their required qualifications to sailit.

Superyachts and luxury yachts are a different league - expect to pay $15,000 a day and up to $100,000 a day if your budget can manage it.

Explore the Caribbean By Renting A Yacht

With everything from top end shopping to desert islands, party towns and of course the excellent sailing conditions, a Caribbean yacht charter can be almost anything you choose. One thing you won't need is your thermals! Book your Caribbean yacht charter holiday with Borrow a Boat today!


Is Yacht hire in the Caribbean Legal?

Though it is heavily restricted in Cuba, yacht charter in the Caribbean is legal. As with driving a car there do keep your documents to hand as it is a legal requriement to present your ID, licenses, insurance documents and charter contract on demand by the Marine Police or US Coastguard.

What kind of Yachts can I hire in the Caribbean

You can hire a motorboat, RIB, catamaran or sailboat on bareboat terms in Belize, or you can hire a skipper to help you. For a luxury yacht or super yacht you will hire the crew and skipper as part of the package.

What should I consider when hiring a Yacht?

Consider your budget, sailing experience, whom you are taking sailing and where exactly you wish to go. Have you the sailing qualifications to do the trip? They can be very tight as to these requirements.

What are the best time to hire a Yacht in the Caribbean?

November to May is the main sailing season in Belize, with the cooler months of March and April said to be the very best.

Do you have to pay a deposit when hiring a Yacht in the Caribbean?

You will typically pay 50% upfront on booking the yacht hire and the balance on arrival. You will either pay a security deposit with your credit card on departure or can get insurance covering damage in advance.

What happens if my Yacht breaks down?

If you are at sea and in danger, call MAYDAY on VHF Ch16. If you have a mechanical fault and can make it to/are on a mooring you will be able to phone a number given by the yacht charter company.

What should I think of before I hire a Yacht in the Caribbean?

You should consider do you have the experience to handle the yacht charter you want to book and where do you want to go. Bring warm weather and cool weather clothing if it looks like the weather can be cool as well as warm in Spring and Autumn - but at sea it can be cool on most evenings.

Do I need a visa to visit the Caribbean?

This can vary. Cuba is the most restrictive - you will need a Tourist Card from the Cuban Embassy before you arrive. You will have to pass through Customs almost every time you sail between islands - a frustrating part of life in travelling in this region.

The Caribbean is a mix of independent countries and those ultimately ruled by different European countries or the US. Depending where you are from will impact on how long you can stay - a Brit visiting a French island may not be able to stay longer than 90 days for instance.

That said for most yacht charter holidays or a week or two, you should be fine - keep your passport stamps as a souvenir!

Frequently asked questions
What should I consider when renting a Yacht or Boat?

The main points to consider are what is your budget, have you got the necessary sailing experience and qualifications to manage the boat if it's not going to have a captain, whom you are taking sailing, where exactly you wish to go and what will the weather be like on the proposed dates of your trip.

Do you have to pay a deposit when renting a Yacht in Antigua?

​You will typically pay 50% up front on reservation the yacht rent and the balance on arrival. You will either pay a security deposit with your credit card on departure or can get insurance covering damage in advance. In some cases (such as the recent Covid situation) charter companies may be more flexible but this depends on the individual charter companies themselves.

What happens if my Yacht breaks down?

If you are at sea and in danger, call MAYDAY on VHF Ch16 or ring the coast guard on your phone if you have reception. If you have a mechanical fault and can make it to or are on a mooring you will be able to phone a help line number given by the boat charter company.

What should I think of before I rent a Yacht or Boat in Antigua?

You should consider do you have the experience to handle the yacht charter or boat rental before you book and where do you want to go along with what the weather will be like. Bring warm weather and cool weather clothing if it looks like the weather can be cool as well as warm and remember at sea it can be cool on most evenings.

What Qualifications Do I need to rent a boat or yacht?

If you want to sail without a captain then you will need relevant qualifications like RYA Day Skipper/International Certificate of Competence (ICC)/ASA 104 Bareboat certificate or the US Sailing Certificate. For small 'day boats' or if you choose to have a captained on board your yacht charter you typically don't require licences.

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