The Caribbean

Traditional Sailing and Winter Sun

The Caribbean sailing season extends from mid-December to the end of April, and offers a fantastic playground for winter sailing in the sunshine. Many people’s image of the Caribbean is of lazing on palm-fringed beaches with a cocktail in hand. That’s all well and good, but the reliable trade winds also offer some properly exciting sailing, and there is so much to explore here, especially off the beaten tourist trail. Caribbean culture is vibrant and welcoming. Fantastic music, fantastic people and fantastic food. All in all this makes for a pretty perfect sailing holiday- great days’ stonking along under canvas, with evenings in stunningly beautiful anchorages or ashore, soaking up the atmosphere. Happy days!

As a sailor you will realise it’s easier to sail from the Windward Islands downwind to the Leeward Islands. In essence many of our Caribbean voyages follow this principle, although there are also plenty of round trips to choose from. Less frequent but worth looking out for are voyages to the Greater Antilles.

The selection of voyages is always changing, so sign up to our newsletter and keep an eye on our latest social media posts for new voyage announcements, if you don’t find your ideal trip straight away.

Greater Antilles

This group includes larger islands like Cuba, Jamaica, Hispaniola (containing Haiti and the Dominican Republic), and Puerto Rico. Situated further North and West than the smaller islands of the Lesser Antilles, the Greater Antilles are less often visited by ships sailing a North Atlantic circuit. It can make sense from a passage planning point of view to land at Antigua or St Kitt’s, and then strike out for Bermuda before setting a course Eastward across the Atlantic. Doing this you miss out the Great Antilles altogether.

While they don’t often pop up on our schedules, when they do the voyages to the Greater Antilles are worth the wait. These islands are brilliant to visit under sail- avoiding the resorts and getting under the skin of the real Caribbean.

Lesser Antilles

The Southern part of the Caribbean is made up of many smaller islands, known as the Lesser Antilles. These are further divided into Windward and Leeward islands. For those of you new to sailing lingo, ‘windward’ means upwind, leeward means downwind. The trade winds here run East to West, and Atlantic currents push Northward up the coast of the Americas. These two combined mean that a ship approaching the Caribbean having crossed the Atlantic from Europe will reach the Southernmost islands of the Caribbean first. These became known as the ‘Windward Isles’ (basically Dominica and all the islands to the South of it). Guadeloupe and all the islands North of it were reached later, and were dubbed the ‘Leeward Isles’. As with so many things, it’s the European viewpoint that won out when it came to geographical naming conventions…

Windward Islands

The main Windward islands are Dominica, Martinique, St. Lucia, St. Vincent, Grenada, and the Grenadines. The climate here is a bit wetter (especially further south), which feeds the lush rainforests. The islands are dramatic, with steep volcanic profiles. Think of the Pitons of St Lucia and you get a pretty good idea of the landscapes here.

The fertile farmland of the Windward islands gives them a more rural and traditional feel than further North. There is a stronger African-Caribbean heritage visible in music, food, and festivals, with French Creole culture prominent in Martinique, St Lucia, and Dominica.

Leeward Islands

The main Leeward islands are the British and American Virgin Islands, Anguilla, Antigua, Saint Kitts, Montserrat, and Guadeloupe. It’s drier here, with some of the islands semi-arid. Volcanic activity means there are still some dramatic peaks, but there are also more low-lying coral islands with long sandy beaches.

Tourism is more developed in the North, and there is a strong British colonial influence, with remnants of forts and naval history (Nelson’s Dockyard in Antigua is a fascinating visit- the world’s only remaining continuously working Georgian dockyard). Anguilla and St Martin bring in a French/Dutch flavour to the culture.