Caribbean Yacht Charter | Yachts & Guide 2026-27

Caribbean Yacht Charters

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Perhaps the best tropical yacht charter spot worldwide, there are over 700 islands to choose from in the Caribbean. However, Caribbean yacht charters can be split into two main area: the Greater Antilles and the Lesser Antilles. The Greater Antilles is home to countries like the Dominican Republic, Jamaica and Cuba while the Lesser Antilles can be subdivided into the Windward and Leeward Islands. The Leeward islands include St Kitts and Nevis, the British Virgin Islands, Anguilla along with Antigua and Barbuda. The Windward Islands comprise the Grenadines, Grenada, Barbados, Dominica, St Vincent and St Lucia.

ALFA NERO | From EUR€ 812,000/wk

Oceanco

MALTESE FALCON | From EUR€ 480,000/wk

Perini Navi

SEVEN SINS | From EUR€ 270,000/wk

Sanlorenzo

SEVEN SINS offers a fantastic beach club

G2 | From US$ 85,000/wk

Vitters

Sailing Yachts Under 100' - Sailing Yachts Over 100' - Motor Yachts Under 100' - Motor Yachts Over 100' - Catamarans Over 50'

The stunning and diverse Caribbean beckons travelers back year after year. With its beautiful climate, fantastic coral reefs, palm trees and exotic tropical islands, there are lots of reasons to make this your next sailing destination. Don’t forget the rum cocktails either! As the second largest yachting area, only after the Mediterranean, there are many luxury yachts available for your Caribbean yacht charter and you can view some of the yachts below or here.

Reviews of Caribbean Charter Vacations | Caribbean Holiday Fact File | Top Caribbean Spots | Sample Itinerary | Charter Yachts Available

The Bahamas and Turks and Caicos are not really in the Caribbean although are known as superyacht destinations in the Caribbean. Wherever you decide to charter a luxury superyacht in the Caribbean you will enjoy a totally relaxing vacation and beautiful scenery.

How Much Does it Cost To Charter in The Caribbean?

Caribbean yacht charter prices vary according to the size, style and age of the yacht you rent. Our luxury superyacht charters rent from 30,000 USD to over 1,000,000 per week, plus expenses, in the form of an advanced provisioning allowance (APA). Conversely, smaller 'all inclusive' type vacations cost between USD 15,000 to 50,000 per week. View the list of yachts and prices here.

Caribbean Islands Map

Experience the luxury of Crewed Private Yachts in the Caribbean

A traditional hot spot for crewed charters, the Caribbean is considered “the king of yachting vacations”, so please contact us here to go on your private charter. Whether you agree with this or not, you like most people will have heard of the Caribbean as a great yacht charter destination. This is because this location covers a huge area and offer fantastic diversity. It is beautiful and warm, has amazing beaches, interesting cultures and perhaps most importantly, the Caribbean has a huge selection of crewed yachts, luxury yachts and superyachts which you can rent and experience a truly magnificent vacation around the various Island groups. The Caribbean is a natural wonderland onshore, but probably most importantly, it has an ocean laden with treasures, from tiny beach ridden coral atolls to substantial mountainous islands exuding rich and colorful cultures. An area which is famous for its beautiful waterways and islands, there is no better way to experience the Caribbean than on a crewed luxury yacht vacation.

Some of the Recommended Caribbean Yacht Spots:

Popular places to visit on a yacht include Antigua, St Barts, Anguilla, St Martin, The British Virgin Islands, The US Virgin Islands, the Grenadines and many more – see more below.

More than ever crewed luxury yachts are beginning to explore more exotic and remote Caribbean Islands, so ask your charter broker or captain for more information on some of these more remote treasures. Due to the scale and diversity of the different areas of the Caribbean we have covered the major charter locations individually. Please note that if there is a charter boat cruising area, not covered here that you are interested in, please contact us and we will provide you with that information personally in the form of a yacht charter itinerary.

As one of the most popular locations in the world, second only to the Mediterranean in popularity, the types of boats available for rental in the Caribbean include all the main types such as motor, sailing, skippered, crewed yachts, catamarans, power boats, sailboat, luxury yachts as well as the ever growing superyacht and mega yachts. Both beginner and experts alike are drawn to the Caribbean for its warm winds, protected waterways and beautiful anchorages. The Caribbean is a special place that has beautiful tropical islands that lie snug within a tropical island necklace as laid out on a large blue sea.

The Caribbean is also steeped in a fertile history of sailing adventure. Ever since the days of galleons and pirates the Caribbean has been host to some of the most satisfying sailing anywhere in the world. On your Caribbean yachting vacation you can find, an incredible amount of choice and variety and all in a relatively small area - thriving bars and Caribbean nightlife; first rate cuisine; spectacular white powder beaches; lush tropical rain forest; cloud-fringed mountain peaks; exotic bird life; amazing diving and snorkeling and a serene blend of European sophistication and warm Caribbean hospitality. The problem is, with so many superb Caribbean yachting locations and charter boats to choose form, where do you start when planning a holiday? With CharterWorld of course…

The Time of Year to Charter a Yacht in the Caribbean:

The main Caribbean sailing season runs from November through to July. The Caribbean primary high season is from mid-December to March, when the winter escapees from North America and Europe arrive in their greatest numbers. The hurricane season is from late July to early October, although hurricanes are in general rare in the southern Caribbean. Unfortunately, they can be prevalent around Cuba, Bahamas and the east coast of the U.S. every few years. This is the least expensive time for chartering in the Caribbean and there are some really good deals are available. However, as well as running the risk of storms, this time of year also tends to be associated with lighter (or non-existent) winds.

As with many boating locations the Caribbean shoulder season, in this case from April to July, is also a great time to charter a boat as there are less shore based visitors, some lovely settled sunny weather, and warm yet steady breeze. The Caribbean is made up of many different multi-nation (and multi-cultural) volcanic islands. There are amazing sailing grounds stretching from Cuba and Jamaica in the west, through the Dominican Republic, Puerto Rico, The Virgin Islands, The Leeward Islands and the Windward Islands, finishing with Trinidad and Tobago off the coast of Venezuela.

Caribbean Yachting Hot Spots:

Here is a brief list of some of the Caribbean hot spots to consider experiencing when you rent a luxury crewed charter yacht. This is by no means an extensive list and there is more information on things to see and do in the Caribbean under each Caribbean private yacht location. Also, when you hire a yacht with us we will supply you with a customised hand written itinerary suggestion so that you and your crew have a few ideas to choose from on your charter.

General Places/Events Worthy of Experiencing:

- Gustavia Harbour in St Barts - shopping, nightlife, restaurants and European quintessence
- Nelson in Dockyards in Antigua - history and beauty in a harbour
- Sunset in St Lucia
- St Kitts for the beauty, history and magnificent views from Brimstone Hill Fortress
- Anegada for its deserted beaches, fringed reefs and the unique flora and fauna of the salt ponds, home to the pink flamingo
- The BVIs for the beautiful beaches and anchorages
- Guadeloupe for its diversity - one side offers cosmopolitan flair, bordered by beaches and coral reefs and the other has open lands with the fertile, volcanic peaks , rain forest and waterfalls.

Yacht Harle - Caribbean

How to get to the Caribbean

There are direct flights from the UK and the US to Barbados, Jamaica, St Lucia and Antigua. Some Caribbean islands require a connecting flight as they have small airports which cannot handle large aeroplanes. Across the Caribbean, many islands have private jet facilities with fantastic runways.

What is the currency in the Caribbean?

Various currencies are used in the Caribbean. For instance, in Anguilla, Dominica, Grenada, St Kitts and Nevis, St Lucia, St Vincent, the Grenadines and Antigua, the East Caribbean dollar is the currency. Jamaica, Barbados, the Cayman Islands and the Bahamas have their very own currency. US dollars are accepted on most of the islands however the ATMs tend to have only the local currency.

Language spoken

There are four main languages spoken in the Caribbean, French, Spanish, Dutch and English. English is the first or second language and is mostly used when tourists visit. The official language of Haiti is Haitian Creole while Papiamento is used in Curacao, Bonaire and Aruba. Different creoles and local patois are also spoken on the various islands.

Time Zone in the Caribbean

Two time zones are used in the Caribbean. GMT -5 and GMT -4. Daylight saving time is implemented in many countries including Bermuda, Cuba, Haiti, the Bahamas including the Turks and Caicos Islands.

Visas and customs immigration

British and American tourists do not need visas if they are staying in the Caribbean for less than 90 days. It’s advisable to check the exact requirements for the countries you intend visiting. American tourists are still not allowed to visit Cuba although this may change in the future.

What to consider medical/health wise when chartering a superyacht in the Caribbean

There aren’t any extra medical issues for travelers in the Caribbean but check with your travel agent for any current warnings. The most common are complications form insect bites, jelly fish stings, cuts from coral and heart-related illnesses.

Short List of Caribbean Sailing Yacht Events:

- Antigua Sailing Week – held during the last week of April each year, yachts from all over the world arrive in English and Falmouth Harbours for an action packed week on fun sailing.
- St Bart’s Bucket
- Grenada Sailing Festival
- Heineken Regatta – a Caribbean sailing and party Regatta – The Heineken St Maartens.
- Here is the full list of Caribbean yachting and sailing events.

95m (312ft) · Golden Yachts · 2020 · 12 Guests

From EUR 1,100,000 / week

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All Yachts in Caribbean

Client Testimonials

What our clients say about their charter experience.

They absolutely loved the boat and described it as phenomenal. The meeting with the captain at a café the day before departure was excellent and helped establish a great rapport. They loved the flexibility of having the captain tailor each day around their preferences. The boat would typically move in the morning, although some evenings they would travel as well. The food onboard was exceptional. They did not want to miss a single meal and were consistently impressed with the quality. The crew's service was a major highlight. They loved that the crew knew one another well and were all Croatian, which created a very warm and cohesive atmosphere. The crew offered two massages each day, allowing everyone to take turns enjoying them. The captain would regularly go into town to purchase fresh produce and local fish, which added a wonderful local element to the experience. One day, the captain went out diving for octopus and later enjoyed it as part of their onboard meal. Overall Takeaway: The clients were exceptionally positive about the trip, with the yacht experience, crew, flexibility, food, and personalised service standing out above everything else. They repeatedly emphasised how much they loved being onboard and how little they wanted to leave the boat.

What can we say? Unbelievably amazing experience. You are all such wonderful people whom we can now consider friends we hope to have long into the future. Thank you for sharing your hospitality and incredible country with us; we could not have asked for a better experience. We look forward to seeing you all in the very near future – in Croatia or Florida. All the very best and with much affection

Thank you all so much for such an amazing week! We had such a fabulous time thanks to each & everyone of you! Looking forward to seeing you in Dublin.

You guys knocked it out of the park again – we had such a super time! Thanks again to all for looking after us so well and all welcome in Dublin at any time!

Spectacular in every way! We were only your third charter, yet seeing how well all of you already mesh with each other and us (especially on the dance floor!) was a delight in itself. Unlike some other charters our Primary has made, she said you were excellent at offering ideas on where to go and what to see. You were all exceedingly professional and constantly helpful, caring and pleasant, which made this adventure even more memorable. I’d say you are like family, but you’re better than family. The thoughtfulness in every aspect of design, and the ongoing attention to cleanliness and comfort were immediately evident. And the food – oh, the food – Always outstanding. No one wanted to leave this beautiful vessel, but since we have to, know that memories of you and this life-changing experience will make us smile all the rest of our lives.

Thank you so much for the wonderful time you have all given us this week. The boat is beautiful but you all made it with your warm personalities, kindness and care every day – the food and cooking was amazing, your brilliant cocktails and the help with all the watersports made it such great fun. Thank you for your professionalism and smiles – we have great memories to cherish