Bareboat destinations in the Caribbean including The Virgin Islands, Leeward Island and Windward Islands including the Grenadines.

The Virgin Islands

By far the most popular charter area (and the easiest to sail) is the Virgin Islands. These Islands are more sheltered from the open ocean than other Caribbean areas, they are much closer to each other and there are numerous quiet anchorages. You rarely need to sail more than an hour or two to get from one place to the next, and will quite often stop somewhere for lunch and end up somewhere else for dinner.

If you are a first time Charterer we strongly recommend the Virgins unless you have prior Blue-Water experience. This is unquestionably one of the finest sailing areas in the world and very easy to navigate. There are dozens of quiet anchorages to enjoy, many excellent spots for diving and snorkeling, a variety of shore excursions are possible and you can always find something going on in the evening, it that's your goal.

You can start your bareboat charter in either St. Thomas or Tortola.

The advantage to starting in St Thomas is that flights are less costly, more airlines fly there and you can get direct flights from the USA. You don't go through customs on the way in from the USA, and so you can bring as food and drink with you without worrying about import restrictions. Provisioning on St Thomas is easy and a little less costly than on Tortola. You can visit St John on the way to the British Virgin Islands, where you can still find some relatively uncrowded anchorages.

The advantage to starting in Tortola is that you are in the heart of the prime cruising grounds and, unless you must visit St Thomas or St John, will not need to enter or clear customs, as you will if you start in St Thomas. Your bareboat company will be closer and they'll be able to reach you quite quickly by chase boat, should this be necessary. Provisioning is a little more costly than it is in St Thomas.

You'll either have to take a small commuter flight from San Juan to Tortola, or else fly into St Thomas and take a ferry to Tortola (slightly more than $50 per person, round-trip). The only problem with chartering in Tortola and flying from St Thomas is that you'll probably have to take the 8 am ferry back from Tortola in order to make your afternoon flight home, as there isn't another ferry until noon.

The Leeward Islands

These islands lie southeast of the Virgins. St Martin, St Barts, St Kits, Anguilla and Antigua are most easily recognized names. Unless you care to stay close to home you'll do some day-long passages in this area, often in fairly rough conditions. For those who enjoy lots of sailing the Leewards are an excellent choice.

One of the things that's particularly Appealing about this area is the variety in both topography and cultures. Some islands are high and mountainous while others are low and sandy. Some islands were British and are now independent, like Antigua and St. Kitts. Anguilla remains a British protectorate, while St. Barts is French and St. Martin half Dutch and half French. Fierce battles were fought by the European nations for control of these islands before the days of refrigeration when salt, spices and sugar were valuable commodities used to preserve food. Each Island has it's own unique culture and is of great interest to history buffs. Excellent seven and ten day itineraries are possible in this area, and one-way sails between St. Martin and Antiqua can be arranged. One advantage to sailing in this area is that non-stop flights are available from the USA to St. Martin.

The French West Indies

The romance of the Caribbean comes alive in the French islands of Guadeloupe and Martinique, which lie mid-way between the Leeward and the Windward islands. There are fewer yachts cruising this area than others due to licensing restrictions by France. Some knowledge of French is useful when sailing here as the majority of the people you'll run into speak little if any English. The standard of living is higher in the French Islands than in those that were formerly British. Apparently French colonialism was kinder to the Island residents under their jurisdiction.

We particularly recommend stopping at the small group of islands just south of Guadeloupe known as the Isles des Saintes. You'll love them. In between Martinique and Guadeloupe lies the Island of Dominica (not French), one of the most lush and under-developed countries in the Caribbean. While the anchorage here is not the most comfortable (you'll probably roll if you don't set a stern anchor and align yourself with the swells) a tour of the island's interior is well worth the inconvenience.

There are some fairly long sails required in the French Caribbean, but much of your sailing is in the lee of a large island and rough passages between the islands rarely last more than three or four hours.

The Windward Islands

The seas are rougher going than in the Virgins but calmer than found in the Leewards, and sailing here is a logical progression after several charters in the Virgins. The highlight of your cruise is sailing in the Grenadines, which lie between St. Vincent and Grenada. Visiting the Tobago Cays is a must.... the water colors are so spectacular that you'll have a hard time believing your eyes!

Distance between islands is not as great as in the St. Martin area once you get down to the Grenadines. However there is a day-long sail from St. Lucia down to Bequia (the most northern of these islands) or a day long sail up from the southern end of Grenada to Carriacou, just south of the Grenadines. The Island of St Vincent is at the Northern end of the Grenadines. Union Island is smack in the middle of the Grenadines, but does not have very good air service.

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