Skip to main content

Caribbean Sailing - Cuba, Puerto Rico, Bahamas and Turks and Caicos

Caribbean Sailing Ground - St Martin to Bahamas

After the sophistication of St Barts or St Martin, the Caribbean chain takes a different turn. A 60 mile gap of open ocean seperates Northernmost island of Anguilla from the Virgin Isles.  There is even more open sailing to seaward of Puerto Rico and the Dominician Republic before you reach the divers mecca of the Turks and Caicos Islands.  They lie at the SE end of the Bahamas and many of the islands in the group are uninhabitied with coral reefs, white sands and mangroves.  Humpback whales migrate through here between December and April each year.  Between the Bahamas, Florida and Jamaica lies the long coastline of Cuba.

Latest Voyages
Vessel Start Date End Date Start Port End Port Price
Why we love this sailing ground

Anguilla, St Barts, St Martin (Sint Maarten)

On your way north from Antigua this group of islands offers lots of short but invigorating passages. The whole of Anguilla's coastline has offshore reefs and are rich in fish. Unusual destinations might be Prickly Pear Cay - an offshore desert island with a remote beach bar !

St Barts (St Barthelemy) has the allure of a small island whose economy has always been intricately linked to its excellent harbour. The fine harbour and many sheltered bays for ships meant that it was fought after by the British, Spanish, French, pirates and was eventually given to the Swedes by the French in exchange for free port rights to Gothenburg ! The Swedes made St Barts a free port which it remains today, which is a major reason for its prosperity.

Bahamas style sailing. This is not your charter boat !
Bahamas style sailing. This is not your charter boat !

British Virgin Isles

The definitive favourite for Caribbean yacht charter, the British Virgin Isles offer a vast variety of islands and anchorages to explore, wonderful sea swimming and many wooden jetties and waterside bars.

San Salvador - First Landing place of Columbus

If you want to take part in Classic Sailing skippers facination with remote islands then San Salvador is a good one for your logbook. Even a google search on the computer failed to turn up any more information about the first landing place of Columbus.  (Not to be confused with El Salvador !)

Turks & Caicos - Manta Rays

The Turks and Caicos Islands are about 40 low lying islands perched on on the Southeastern end of the Bahamas island chain.  The Caicos typical wild landscape is arid limestone lacking vegetation apart from dense coastal mangroves. They sit on a vast sandbank creating wonderful swimming and those classic turquiose seas that are so bright you need sunglasses on at breakfast time.

Eyeball Navigation Tips in the Caribbean: Always enter an anchorage with coral reefs with the sun behind you and a good pair of polarised sunglasses to spot the coral heads. A high vantage point for the lookout is ideal"

coral reefs make navigation interesting as they grow so charts are not always accurate
coral reefs make navigation interesting as they grow so charts are not always accurate

Humpback Whale Migration

The Turks are separated from Caicos group by the Turk Island Passage with a massive ocean trench 1.2 miles deep. A quintessential sleepy Caribbean set of islands that is quietly one of the top dive locations in the world. Even from the deck of a ship you could potentially see manta rays underwater- especially off the walls of the oceanic trench. Between December and April the Turks & Caicos islands sit in the path of the annual humpback whale migration.

Humpback whales have distinctive white flippers as well as a humpback
Humpback whales have distinctive white flippers as well as a hump.

Tall Ship in the Bahamas

The Bahaman chain consists of 700 islands and 2000 smaller sandy cays extending for some 750 miles from South East of Florida to Cuba. The combination of deep oceanic trenches and shallow seas around the islands creates a mecca for divers. They come seeking large wildlife encounters with dolphins, barracuda and sharks in crystal clear visability (regularly down to 100ft or 30m). Over 5 % of the worlds coral reefs are in the Bahamas so bring your diving mask or at least a pair of tinted swimming goggles.

Slightly more bizZare are the feral pigs on Exuma that like to swim in the sea.

1950's American cars are what many tourists think are the iconic images of Cuba
1950's American cars are what many tourists think are the iconic images of Cuba

Cuba

A hot steamy country with music on street corners and a coastline ringed with coral cays and offshore islands. Few Cubans have cars and cycling is becoming a popular mode of transport when you have had enough sailing. Tobacco and sugar cane are still important crops and the pre historic interior landscape of the Vinales is worth a visit.

Salsa and Latin rhythms still runs through the veins of every Cuban in a country where time seems to have stood still. The crumbling architectural grandeur, big american cars of the 1950's sit strangely with the "Socialism or Death" signs and images of Che Guevara and Castro. There are still restrictions on American's visiting. It has to be for a cultural and educational purpose which has created some inventive tourism enterprises where you can stay on a tobacco farm, learn to salsa or cycle with a guide around Havana.

Accommodation is incredibly cheap here so if you are sailing with us to or from Cuba, then it is well worth staying a few days. Founders of  Classic Sailing Adam and Debbie Purser sailed to Cuba on Oosterschelde in March 2018.

Read their travel blog LINK

 

Sailing in Cuba on Oosterschelde. Local musicians in Havana
Sailing in Cuba on Oosterschelde. Local musicians in Havana

Puerto Rico, Dominican Republic and the Spanish Isles

Blue Clipper will be the first of our ships to sail around Puerto Rico, Vieques, Culebra, Dominican Republic and Cuba. With unspoiled white sandy beaches, crystal waters, palm tree lined coasts, lush rainforests and historical cultural sites. 

The Islands of the Spanish lie in the North-eastern part of the Caribbean between the islands of Cuba and Puerto Rico.  The Dominican Republic occupies two thirds of the eastern side of Hispaniola, a popular and inviting destination.  Be enticed by the local gastronomy served at the many fine restaurants here .  One such famous dish being "pescado con salsa de coco" - fish in coconut sauce.  It is simply delicious.  

Puerto Rico and its neighbouring Spanish Virgin Islands are rather isolated yet beautiful destinations. A tropical paradise with extensive beaches and mountainous interior attracting all to its shores.  Nowadays, the island has a diverse blend of cultures influenced by Spanish, West Indians, Africans and Americans.  Take a trip inland to visit the El Yunque rainforest.  The views are simply stunning as are the impressive waterfalls and exotic wildlife.  

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.  Perhaps anchor in the world famous Puerto Mosquito (Mosquito Bay) Located on the southern shore of the island of Vieques, this magical bioluminescent bay has been officially declared the brightest recorded in the world by Guinness Book of World Records 2008. If you have ever wanted to swim amongst glowing phosphorence plankton this is going to be the warmest place to do it!

Puerto Rico jungle shorelines
Puerto Rico jungle shorelines

US citizens - on your doorstep ?

There are American owned tall ships sailing in the Caribbean but few are true 'hands on' sailing adventures where you are  relied on to be the crew, stand watches, steer the ship and work aloft (correct us if we are wrong). So if you are a sun starved Canadian or a US citizen who lives just accross the water in Miami there is nothing to stop you signing up to sail. Please check visa requirements for Cuba with your own embassy.

Caribbean style Itinerary

As with all our sailing holidays the Captain has many considerations to plan for when choosing the weeks itinerary so these islands are only an informed guess at where you might sail. 

Weather, swell from unusual directions, customs clearance regulations and new marine wildlife reserve anchoring restrictions or even booking an alongside berth to change crews, fuel or water the ship can all affect the plans. Even the time of day and whether the sun is ahead or behind you, can influence pilotage in these coral reef strewn coastlines - but it is all fascinating stuff the the Captain or mate will brief you each day to explain the latest plan !

Celebrate the prohibition rum runners with a bit of Cuban Rum
Celebrate the prohibition rum runners with a bit of Cuban Rum
Which ship for my adventure?

Blue Clipper 

Dutch three masted schooner has been to Cuba and the Northern part of the Caribbean in 2017 and 2018. She even took part in the first tall ships race in the Gulf of Mexico. Having seen this impressive schooner with her black hull and white flash on the bow the residents of Galveston in Texas, New Orleans and St Petersburg, Florida will not be slow in signing up for any future Caribbean trips. 

Destination Vessels
North, South, East or West?

 Zoom in and explore 

Regions

What others say about us

CURRENT AVERAGE   4.6 STARS
249 REVIEWS

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

Experts

Office Team of 4 Skippers

6 Times Around the World between Us

Selling Holidays for 22 Years

3 Dogs to make us laugh

Contact Us

How to Book

Voyage Applications Online 24 /7

How to book a voyage

Terms & Conditions   Travel Insurance

Office open Mon - Fri, 9 - 5

Frequently Asked Questions