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Caribbean Sailing Holidays on Tall Ships

The Caribbean is perhaps the most perfect sailing ground in the world in terms of wind, sunshine and variety of places to visit. What could be better than island hopping on a barque or three masted schooner in brisk trade winds, with the canvas sails white against the blue skies driving you along without fossil fuels but also offer cooling shade on wooden decks. On Classic Sailing ships you are participating in the sailing as crew so you can go ashore for a rum punch, talk to locals about your voyage, or a wander along another beautiful beach satisfied you have earned your place in the tropical sun.

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Why we love this sailing ground

The Caribbean for Trade Winds & Tropical Sun

The whole Caribbean Island chain from Grenada to Cuba  is perhaps the most perfect sailing ground in the world in terms of wind, sunshine and variety of places to visit. The Windward and Leeward Island Groups sits squarely in the North East trade wind belt and Classic Sailing only offer voyages outside the most typical hurricane season. Our tall ships revel in strong winds and boisterous turquoise seas and the canvas sails look magnificent against the deep blue skies. 

Rowing ashore. Grayhound Sailing Lugger explored the Caribbean in 2013.
Rowing ashore in the gig. Grayhound Sailing Lugger explored the Caribbean in 2013.

The Real Pirates of the Caribbean - Lush rainforests, mountains and waterfalls

There is few things to beat a tropical sunset below the yard arm whilst at anchor in a timeless setting. A sailing ship as your base gives you access to the unspoilt Caribbean; Fishing villages where the chickens roam the shore, or landing like an early explorer on a remote beach anchorage under a forest covered volcanic peak. 

If you have been dazzled by the natural scenery in the 'Pirates of the Caribbean' movies then both Guadaloupe and Dominica are much closer to that lush volcanic island paradise than more well known Caribbean tourism locations.  The second movie 'Dead Mans Chest' and 3rd Capt Jack Sparrow adventure At 'World's End' were filmed in the rain forests of Dominica, close to Guadaloupe.

Fishermen with dug out canoes in Dominica
Fishermen with dug out canoes in Dominica

Coral Reefs & Marine Wildlife

Some of the best dive sites in the world are in the Caribbean, but you don't have to be a diver to enjoy them. In Scott's Bay, Dominica you can swim off the beach with a snorkel and face mask and swim from shallow coral and 12ft of water to a sheer underwater wall of coral and cliff - descending 4000ft. Alive with fish and coral and upwelling plankton, this sunken volcanic crater is also deep enough for Sperm Whales to swim close inshore. Further North the Bahamas Banks contain approximately 5 percent of the worlds coral reefs and the crystal clear visibility over white sand bottom means you may see sharks, dolphins and turtles from the ships deck without getting wet.

Some of the best dive sites in the Caribbean can be enjoyed with a snorkel
Some of the best dive sites in the Caribbean can be enjoyed with a snorkel

Sailor to Sailor - Connect with Caribbean Island Life

The cliche is that the Caribbean is very laid back.  The reality is that every island community and culture is different. Compare the French sophistication and fashion concious young people of Guadaloupe and Martinique, where people watching is an art form, to the Caribs of Dominica pushing their solid dugout canoes out into the ocean with hand woven fish traps.

tall ship crew
Picton Castle crew finding it quite easy to relate to the local fishermen in their ships boats
Which ship for my adventure?

Blue Clipper - Three Masted Schooner in the Caribbean

Blue Clipper sailed to Bermuda in 2017, but she is heading for a whole winter season in the Caribbean in 2018. She has a couple of voyages from Bridgetown, Barbadosaiming to explore the Windward Islands  including Martinique, St Lucia, St Vincent, the Grenadines and Grenada. She is then pioneering a new area for Classic Sailing. Puerto Rico and its neighbouring Spanish Virgin Islands are rather isolated yet beautiful destinations. A tropical paradise with extensive beaches and mountainous interior and rainforest.  Nowadays, the island has a diverse blend of cultures influenced by Spanish, West Indians, Africans and Americans.  The Spanish Virgin Islands are a group of islands and reefs east of Fajardo.  The main areas are Vieques and Culebra, two unspoiled, undeveloped islands that offer perfect beach days.  

Awning on Blue Clipper in the Caribbean
Sun Awning on Blue Clipper in the Caribbean

Morgenster - Dutch Square Rigger

Morgenster is a brig that carries square sails on two masts and can set stun'sails too. She occasionally does a Caribbean season and with only 24 guest crew this is a laid back way of having fun in the sun. Yes the crew love to teach square rig skills but the style of sailing is more 'shared adventure' than character building sail training in the sun.

Morgenster has voyages from Martinique and St Maarten
Morgenster has voyages from Martinique and St Maarten

British Barques - Lord Nelson & Tenacious

British barque Tenacious and her sister ship Lord Nelson are regular visitors to the Caribbean. So much so, one of their relief Captain's now lives in Antigua. Lord Nelson (or Tenacious) typically offers a Trans Atlantic to Antigua from the Canaries and a few voyages based around Antigua and the nearby Leeward Islands. French Caribbean treats like Guadaloupe and Martinique are not far away either.

Tenacious and Lord Nelson have special features for disabled crew
On Tenacious and Lord Nelson everyone can enjoy the sunset - wheelchair bowsprit runway

Schooner Oosterschelde - Martinique, St Martin, Cuba

Three masted Schooner Oosterschelde typically spends part of the winter in Cape Verde and then she crosses the Atlantic for a short season in the Caribbean. Oosterschelde is a Dutch run historic trading schooner that was built in 1917 to carry cargoes under sail. She has been authentically restored as an adventure charter vessel with elegant and cool below decks accommodation and huge saloon which includes a piano.  Oosterschelde has explored the Southern end of the Caribbean island chain and likes to work out of Martinique with a cruising ground stretches from St Lucia to the Leeward Islands and Dominica.  In 2018 Oosterschelde explored North Caribbean from St Martin to the Turks and Caicos islands, Bahamas and onto Cuba, Florida and Bermuda.

Oosterschelde by Pieter Nijdeken
Oosterschelde by Pieter Nijdeken

Smaller Wooden Boats in The Caribbean - Chocolate and Rum Trade

Sailing Lugger Grayhound has sailed a Caribbean circuit in 2013-14 and Marcus and Freya have many friends in the Caribbean. They are currently concentrating on developing her regular sail cargo runs between France and the UK, may be back in Caribbean in the future. Classic Sailing are keeping an eye on another sail cargo ship called Ceiba that is being built in an eco-shipyard in Costa Rica.

To follow this exciting project go to Sail Cargo Website

Destination Vessels
North, South, East or West?
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South - The Windward Islands

These include Grenada, The Grenadines, Carricou, Tobago, Bequia, St Vincent and St Lucia. Out on a limb about a hundred miles to the East is Barbados.

We occasionally have ships using the Panama Canal with stops en route in the Dutch Antilles or Cartegena.

Middle of the Chain - French Caribbean

Dominica, Guadeloupe and Martinique have French sophistication, wild jungle and waterfalls.

Leeward Islands around Antigua

Antigua is famous for yachting and Antigua Classics is held every year. Our bigger ships often use English Harbour or Falmouth Harbour as a joining port and there are lots of flight choices out here. Nearby is Barbuda, the island with the volcano - Monserratt, Nevis, St Kitts and to the North is St Martin/St Maarten.

Northern Caribbean - Puerto Rico, Cuba and Bahamas

There is a break in the chain above St Martin with the Anegada Passage to cross before you reach the Virgin Isles and Puerto Rico. Further North still are the Turks and Caico Islands and the shallow Bahamas to navigate. Cuba is becoming a regular sailing destination for our adventure charter sailing ships.

Bermuda - Island out in the Atlantic

Bermuda is often considered part of the Caribbean Region but it is actually in the Sargasso Sea and really part of North America. It has coral reefs and beaches so what's not to like.

Schooner Blue Clipper in St Georges, Bermuda
Schooner Blue Clipper in St Georges, Bermuda

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