Skip to main content

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 tall ship, 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 guest 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.

Latest Voyages

There are currently no voyages matching this page.


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 turquoise seas and the canvas sails look magnificent against the deep blue skies. 

Blue Clipper relaxing in a hammock under sail in the Caribbean

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

There are few things which 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 rainforests 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 conscious 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.

North, South, East or West?

Zoom in and Explore

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.



What others say about us


Facebook reviews

"A life changing experience with talented crew who gave us hope for mankind ...and biscuits"

Customer comments

Read what the press say about our holidays

Magazine articles


Why book with Classic Sailing?

The call of the sea

Destinations for sailors & explorers

Over 300 voyages a year

11, 051 customers introduced to

traditional boats and tall ships.

Tell us your sailing dreams


Office Team of Skippers

6 Times Around the World between Us

Selling Holidays for 22 Years

2 Dogs to make us laugh

Contact Us

How to Book

Voyage Applications Online 24 /7

How to book a voyage

Terms & Conditions   Travel Insurance

Loyalty Discounts & Price Match

Frequently Asked Questions