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Caribbean Sailing Holidays

Anchor off your own white sandy beach. Dive into warm turquoise seas to snorkel among the rainbow colours of a coral reef. Relax with a rum punch sundowner on the deck of your yacht while you watch another glorious sunset....

Click on the cruising areas below for more details on sailing in the Caribbean. 


Sailing holidays in British Virgin Islands

British Virgin Islands

Come and see for yourself why the BVI is the most popular cruising area in the Caribbean. Perfect sailing conditions and sheltered passages round the islands make this area a delight for all levels of sailors wanting to relax in a Caribbean paradise. Great choice for a first Caribbean charter.

Sailing holidays in the BVI
Sailing holidays in St Martin

St Martin

This surprisingly little island embodies a dual personality - half French, half Dutch. St. Martin/St. Maarten and the surrounding islands of Anguilla and St Barths offer some of the most spectacular sailing in the Caribbean. Experience beautiful anchorages, stunning sunsets and outstanding restaurants.

Sailing holidays in St Martin
Sailing holidays in Antigua


With 365 palm-fringed beaches and numerous anchorages, Antigua offers excellent sailing round the island. As part of the Leeward Islands, Antigua boasts a spectacular choice of picturesque coves and bays, with fine sand, blue seas and some of the best watersports in the Caribbean.

Sailing holidays in Antigua
Sailing holidays in Guadeloupe


Cruise around this butterfly-shaped island with a French Creole flavour or sail to neighbouring Antigua. On Guadeloupe the beaches are secluded and the smell of fresh croissants and pastries mixes everywhere with the spicy aromas of West Indian cooking in restaurants and charming bistros.

Sailing holidays in Guadeloupe
Sailing holidays in Martinique


Martinique is more relaxed than the Caribbean islands to the north and more sophisticated than the islands to the south. The French influence ensures excellent restaurants. Spend a whole week exploring Martinique or head north to undiscovered Dominica or south to St Lucia.

Sailing holidays in Martinique
Sailing holidays in St Lucia

St Lucia

St Lucia is a tropical treasure trove with some of the most beautiful anchorages in the Caribbean. The beaches are stunning, the nightlife is active and the island has a relaxed atmosphere. From St Lucia you can also explore Martinique, a delightful island with a distinctly French flavour, or head south into the Grenadines.

Sailing holidays in St Lucia
Sailing holidays in Grenadines


Explore these Robinson Crusoe islands with soft white sand, turquoise seas and spectacular coral reefs. The Grenadines are undeveloped and unspoilt. Nightlife is conspicuous by its absence, peace and solitude are unsurpassed, and the dress code - like the lifestyle - ranges from informal to barefoot casual.

Sailing holidays in Grenadines
Sailing holidays in Belize


Belize is located on the Caribbean coast of Central America, South of Mexico. Home to the second longest barrier reef in the world, Belize offers superb calm water sailing, diving and snorkelling, Mayan ruins and more - truly an unspoilt holiday getaway.

Sailing holidays in Belize
Sailing holidays in Bahamas


Cruise the "out islands" of the Abacos, just 1 hour flying time from Miami, an archipelago of pale sandy islands, tranquil bays, sheltered harbours and sleepy historic villages. The beaches are spectacular, mile after mile of white sand and plenty of reefs for fantastic snorkelling and scuba diving.

Sailing holidays in Bahamas
Sailing holidays in Florida Keys

Florida Keys

The Florida Keys are known for their spectacular coral reefs, excellent marina facilities and quiet restful anchorages. Often called "America's Caribbean Islands" the Keys are warmed by the Gulfstream, and, sheltered by the only living coral reef in the U.S., the Keys offer splendid sailing conditions year round.

Sailing holidays in Florida Keys
Sailing holidays in Cuba


Cuba is a magical new destination for experienced sailors with some of the world’s finest beaches, a rich cultural heritage and a vibrant approach to life. Dive and snorkel on some of the most exquisite coral reefs in the Caribbean and when the sun goes down, party to the salsa rhythms.

Sailing holidays in Cuba

"We all had an amazing week and had great support from Helen and Harley. They gave us so many great ideas and recommendations that made the week run smoothly and was more enjoyable. Thanks again for an awesome week!"

Trogir Flotilla 2019 - S.R.

Sailing Qualifications

To skipper a bareboat charter or flotilla yacht, you need to hold a practical sailing certificate equivalent to RYA Day Skipper Practical qualification or RYA International Certificate of Competence (ICC). For charters in Greece, you must now have the ICC certificate. You must also be assisted by at least one competent crew member over the age of 18.

The port authorities in Greece are now insisting on one of the following practical certificates: RYA ICC (International Certificate of Competence), RYA Coastal, RYA Yachtmaster, ASA IPC (International Proficiency Certificate) or the IYT (International Yacht Training) Passport. If you hold an RYA Day Skipper or ASA104 it will no longer be accepted and you need to obtain either an ICC or IPC from the corresponding issuing body (RYA or ASA). If your RYA Coastal/Yachtmaster or ASA105/106 certificate is more than 12 years old and does not have a photo ID, then we would also strongly advise applying for an ICC or IPC. If you are a member of the RYA or ASA, you may qualify for a discount or free certificate, otherwise, you will have to pay. The approximate cost is £50. Please use this link - RYA application for the ICC or ASA application for the IPC.

For charters in Croatia, Malta and the Canaries, at least one member of the crew or the skipper will also need a VHF licence.

RYA qualifications can be obtained by RYA sailing schools in the UK or alternatively choose from one of our overseas centres in Gibraltar, Greece or Turkey.

For Seychelles, the local authorities require an ICC for the skipper of a bareboat or flotilla yacht charter.

For Caribbean and Tropical charters, formal qualifications are not compulsory, however, you should be Day Skipper standard and be assisted by at least one competent crew. A brief sailing resume should be provided to outline your experience.

If you don't hold the relevant qualifications then why not add a skipper?

Sailing Levels

Level 1

Winds force 2-3 (4-11 Knots)combined with generally shorter distances. Good for beginner or intermediate sailors. Line-of-sight navigation but basic knowledge of charts and ability to plot your position required.

Level 2

Winds force 3-5 (7-21 Knots) with approximately 15-20nm per day. Intermediate experience required. Predominately line of sight navigation but an understanding of how to sail in open water.

Level 3

Winds force 4-6 (11-27 Knots) with mileage of approximately 20nm+ per day. Ideal for experienced skippers looking to venture out to new destinations. Day skipper standard but with experienced crew would be recommended.