Caribbean Sea Yacht Charter and Sailing Vacation Guide

About Chartering in the Caribbean

The Caribbean is rightly referred to as a yachting paradise. Perhaps no other destination in the world can offer the range of beautiful islands, diving and snorkeling, clear water, and ideal sailing conditions than the islands of the Caribbean Sea. The waters are idyllic, the sights gorgeous, and the activities endless, providing the perfect adventure and holiday. Key destinations such as the Virgin Islands, St Barths, Antigua, the Genadines, St Martin and St Lucia are almost synonomous with palm trees, sandy beaches and great chartering!

While you can try to hop many of the islands, especially if you’re on a motor yacht, we normally would recommend taking a leisurely pace to fully explore a few islands and to absorb the culture. One of the key aspects of being on Caribbean Islands is to do some “chillin” – to ensure you enjoy the slow, natural and relaxed way of life in these tropical islands.

The islands themselves differ considerably, however they all offer beautiful and sheltered anchorages, palm trees, excellent marine life, and fine white sandy beaches with crystal clear waters. The character of the local people likewise varies from the charming and unspoiled modest Dominican, to the well-to-do and modern French of Martinique.

Caribbean Climate

Caribbean weather is normally very sunny, 12 hours a day, with a few billowy clouds and occasionally scattered showers. The climate is nearly perfect – the daily temperatures are fairly consistent all year round, with an average temperature of 80 Degrees Fahrenheit (27 Degrees C). There is only a 5 Degree difference between the warmest and the coldest months of the year.

The period between December-May is the dry season, apart from the occasional shower. During the Summer, conditions are still ideal with refreshing rain showers. There is a risk of Hurricanes during August and September. The Easterly trade winds that blow all year round and rarely exceed force 5 ensure splendid sailing conditions which, combined with the many beautiful and uncrowded island anchorages, have made the Antilles a boating paradise. High Season is the two weeks around Christmas and New Years, and Easter/Spring Break time. Prices are higher during this time, and it it recommended that you book at least 6 months in advance.

Charter Information about the major Caribbean Islands

Below is a short summary of the key Caribbean islands. We have also written in depth Charter Guides for most, just follow the links if you want more information on luxury yacht charter in the Caribbean. You will also see a link to the charter yachts in the area, if you just want to see our boats. In certain areas we also have itineraries and additional local interest articles.


1. Antigua and Barbuda

The beautiful beaches of AntiguaOnce the primary port for Admiral Nelson's Fleet, Antigua ("An TEE Ga") is now a charter and vacation paradise that offers a tremendous wealth of secluded, powdery soft beaches, stunning coral reefs and numerous beautiful bays.

Barbuda was once a scavenger's paradise because so many ships wrecked on its reefs. It is now home to one of the region's most significant bird sanctuaries, as well as a fantastic place to snorkel.

2. Barbados

Barbados is the most eastern island in the Caribbean, with an area of 430 square kilometres. Under British Rule from the 1600's until 1966 - it is a mix of British, African and Caribbean culture.

Barbados is the only all-coral Caribbean island, providing beautiful white sandy beaches and great diving (but fewer bays and inlets). Visitors can explore Colonial Bridgetown, mangrove forests with monkeys, the Mount Gay Rum refinery and of course miles and miles of beautiful beach.

3. British Virgin Islands (BVI)

Cane Garden Bay on Tortola, BVIA group of British-controlled islands 60 miles from Puerto Rico, the British Virgin Islands (BVI) are a mecca for sailing and yachting. These predominantly undeveloped islands, with beautiful sandy beaches lined with palm trees, excellent snorkeling, and plenty of interesting places to visit, are often recommended as the best place for your first sailboat or catamaran charter.

The BVI trade winds are constant, gentle and predictable, sailing is line-of-site in the protected Sir Francis Drake channel, and each island has its own charm and points of interest such as "the Baths" - a boulder field on a beach on Virgin Gorda that's fantastic for snorkelling and exploring. Key islands to visit are Tortola, Jost Van Dyke, Virgin Gorda, Peter Island, Norman Island, and Anegada each with it's own personality and attractions.

Being the birthplace of bareboat chartering, the BVI has a well established infrastructure for sailing, hundreds of charter yachts to meet just about any need, and plenty of great beach restaurants and boating destinations.

4. Dominica

Because Dominica is the youngest island in the Caribbean, there remains a stunning sharpness to her terrain. Beautiful, dramatic angles abound, rivers run clear and fast and forests remain untouched. The uncompromising beauty of the island is everywhere - rolling hills, secluded coastlines, virgin woods. Dominica is often called “The Nature Island of the Caribbean”. Besides sailing, visit Dominica to hike, raft, bike, dive and generally enjoy the multiple wonders of nature.

5. Grenada

Grenada is a rolling, mountainous island, covered with fragrant spice trees and rare tropical flowers. In the interior of this volcanic island are cascading rivers and waterfalls, lush rainforests, and one of the most breathtakingly beautiful mountain lakes imaginable. The capital, St. George's, is widely held to be the loveliest city in the Caribbean.

Grenada offers plenty of beaches and coral reefs to explore. The island is ringed with miles of picture-perfect strands, including both black (volcanic) and sugar-fine white sand beaches.

6. Guadeloupe

The beautiful coast of GuadeloupeGuadeloupe consists of the twin islands Basse-Terre to the west and Grand Terre to the east, along with several smaller islands. Basse-Terre is a thickly forested mountainous island of volcanic origin. Grand-Terr is a limestone island of coral origin with low hills rising to 150 meters and extending through the central and southern part of the island.

Guadeloupe was a French colony and as a result of its heritage, offers the height of the Caribbean's Creole culture - a blend of French and African influences. The archipelago offers a mix of modern cities, rural towns, rainforests and secluded beaches, as is as well known for its sugar and rum as it is for its beaches and resorts.

7. Martinique

Martinique is truly "A little bit of France in the Caribbean islands." It exudes a distinctly French feeling -- In the excellence of it's caribbean cuisine, the beauty of its language.

The sailing infrastructure of Martinique is well developed, with plenty of charter boats (more catamarans than monohulls) in le Marin. You can explore Sainte-Anne, the southernmost village to Saint-Pierre, famous for the 1902 volcanic eruption of Mount Pelée, sail near HMS Diamond Rock and explore the many wonders the island has along her shores.


8. Vieques and Culebra, the Spanish Virgin Islands

Often referred to as the Spanish Virgin Islands - the islands of Vieques and Culebra lie to the west of the US Virgin Islands and are part of Puerto Rico.

With water depths rarely exceeding one hundred feet Culebra is ideal for snorkeling and scuba diving. Hard and soft corals are found in the shallows and magnificent reefs encircle the island where tropical fish and other sea life abound.

Vieques offers the lush, unspoiled Caribbean of the past with ample diving, hiking, bicycling, horseback riding and several other activities for nature lovers.

9. St Barthelemy/St Barths/St Barts and Anguilla

A view on beautiful St Barths during high season St Barts is more rugged and less lush than islands such as Martinique. Steep hills divide the island into several valleys, usually open on one side to the sea. The shoreline includes around 20 beautiful white sandy beaches, most with a coral reef, and several offshore Marine Reserves.

St Barts is a prime spot for all boats, but it's especially known for its superyachts, as the island is a hideaway for may rock stars and celebrities. It has great cuisine derived from it's French ancestry, but is also quite expensive.

10. St Kitts

A view of a secluded black sand beach at St KittsThe combination of natural beauty, great weather, warm waters, and white sandy beaches make St. Kitts one of the most seductive spots in the Caribbean. Christopher Columbus first spotted St. Kitts in 1493, when it was populated with native tribes, but the Europeans did not colonize until the British arrived in 1623. Its strategic location and valuable sugar trade led to an advanced and luxurious development that was among the best in the Colonial Caribbean.

Development of St Kitts has been well controlled, keeping the island uncrowded and unspoiled. If you enjoy nature you can tour lava formations, tropical forests, and seaside lagoons. Plantation homes with a colonial feel have been transformed into nice hotels, and there are several quaint shopping areas.

11. St. Martin/St. Maarten

The beautiful beaches of St Martin The smallest island in the world ever to have been partitioned between two different nations, St. Martin/St. Maarten has been shared by the French and the Dutch for almost 350 years. Each side has managed to retain much of the distinctiveness of its own national culture. You will find comfort and style on the French (St Martin) side, with secluded beaches, plush accommodations, and restaurants that offer some of the finest dining in the Caribbean. St. Maarten is more bustling and has been developed with more of an informal Dutch flavor.

Boat enthusiasts will find plenty of charter boats on the island, as it's a charter hub and there are several of regattas. It's also a great stopover if you are cruising the Antilles on a yacht.

12. St Lucia

The mountainous terrain of St LuciaSt. Lucia is the sort of island that travelers to the Caribbean dream about--a small, lush tropical gem that is still relatively unknown. St. Lucia has a south Pacific feel to it, with its soaring peaks, rain forests and colorful birds.

St Lucia offers great diving and snorkeling, and exploration of the rainforest and the Soufriere volcano, the world's only drive-in volcanic crater.

13. St Vincent and the Grenadines

A quiet anchorage on St VincentSt Vincent and the Grenadines are remote (most easily reached from Barbados) and therefore not as touristy or glitzy as some Caribbean islands, but just as beautiful! They are the perfect for travelers searching for quiet, getaways surrounded in natural beauty.

St. Vincent is a very lush island that is spectacular in terms of rain forests, high mountains, deep valleys, and dramatic shorelines.

Mustique is 18 miles south of St. Vincent and 110 miles west of Barbados. It is a very secluded island where growth is controlled by the Mustique Company, and offers quite relaxation, beauty and plentiful possibilities for exploration, both on land and in the water.

There are several other small islands - Bequia, Canouan, Union - all beautiful, secluded and great destinations for beach, diving or exploring.

14. Trinidad and Tobago

A deserted beach in TrinidadTrinidad can offer both a bustling city - Port of Spain - and quiet seclusion. The island has gorgeous, sandy beaches and dense forest along our North Coast, and miles of protected beaches and wetlands on the East Coast.

Tobago is less developed than Trinidad, offers the oldest protected rainforest in the Western Hemisphere, and of course has plenty of palm-lined beaches, lush rain forests and pristine coral reefs teeming with rich marine life.

15. US Virgin Islands: St Thomas, St John, St Croix

The three major American Virgin Islands are St Thomas, St John, and St Croix. They form part of the Virgin Islands chain adjacent to the British Virgin Islands.

St Thomas - the most developed island - offers all you would want for a Caribbean holiday - beautiful water, green hills, soft breezes, with an American flavor of efficiency and comfort. You can find just about anything you want on St Thomas - quiet villas, night life, white sandy beaches, golf, interesting cuisine. Its international airport is often the starting place for Americans on holiday, and offers easy boat ferries to the other islands.

St. John is just 20 minutes by ferry from St Thomas, but offers a completely different experience. Two- thirds of the island is a protected National Park offering quiet sailing, breathtaking views and beautiful coves to anchor in for the night or diving.

St. Croix, the largest of the Virgins, lies 40 minutes south of St Thomas. St. Croix, besides the beaches, offers ruins and restorations of sugar mills and plantation houses everywhere. It is less mountainous than St. John and St. Thomas, but offers a wide variety of landscapes, from rolling hills to rain forest, to cactus-covered plains.

Chartering a Yacht in the Caribbean

If you’re chartering a Luxury or Super Yacht, you can start your holiday on any of the major islands – often determined by availability of flights. Those coming from North America often Start in St Thomas, because of the many flights, and Europeans can often more easily get to St Maartin, Martinique, Barbados or St Lucia. Sailing yachts often choose the British Virgin Islands (an easy ferry from St Thomas) - please see our 7 Day Sailing itinerary in the British Virgin Islands or Luxury Virgin Islands Itinerary.

In just about any case, a Caribbean Island holiday will provide ample sun, activities, and chance for both exploration and relaxation!

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