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Caribbean Regions - Sailing in Antigua and the Leeward Islands

Antigua is the most well known island in the Leeward Islands with popular coastal sailing all around a coastline of 365 beaches. There are great harbours like Falmouth and English Harbour that have sheltered great naval fleets over the centuries and now attract everything from millionaires super yachts to more modest wandering  live-a-board yachts.

The Leeward Islands were the Caribbean islands under British influence historically so it includes Dominica, skips Guadeloupe as this was French, and then includes Antigua and everything North all the way to the British Virgin Isles near Puerto Rico. From South to North they include Dominica, Monserratt, Antigua, Nevis, St Kitts, Barbuda, then you run into a cluster of islands that were colonised by the Dutch and French, but from a sailors point of view they are the next geographically to explore. These include St Eustace, Saba, St Bathelemy (St Baarts), St Martin (St Maarten) and then the British Virgin Isles.

This destination page looks at the Leeward Islands around Antigua

Southwards check out our pages on French Caribbean & the Windward Isles

North of the Leeward Isles is another extensive Caribbean sailing ground including Puerto Rico, Turks and Caicos, Spanish Isles, Bahamas and Cuba. See our tips on

 Exploring North Caribbean 

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Why we love this sailing ground

Falmouth & English Harbour - A great Naval tradition

In the old days it was hard to find secure ports in the Caribbean that were easily defendable with immediate access to the trade winds, yet protected enough to careen (lean it over on the beach) a ship and be safe in a hurricane.  Falmouth and English Harbour sit side by side on the South coast of Antigua and meet all those requirements.  If you want to arrive in the Caribbean a few days early then we can recommend the hotel at Nelson's Dockyard in English Harbour is built in the wonderfully restored stone dock buildings.  Tenacious uses the larger Falmouth Harbour with its vast bay accommodating super yachts from around the world. There is usually an excursion to Shirley Heights - the fortified hilltop above the two harbours.  From here you have an amazing panorama of your likely cruising ground from Guadaloupe to the south and the volcano on Monserrat sillouetted in the sunset.

Antigua - 365 Beaches & Yachting Mecca

The island of Antigua has a complex coastline with offlying coral reefs, inside passages and some stunning bays like Five Islands Harbour or Deep Bay with its a three masted shipwreck 'The Andes' with masts still intact.   Captain Claire C of Tenacious's sister ship Lord Nelson lives on Antigua and in past years the ship has spent all winter based here, so the crew know all the best haunts to visit and how to make the most of the boisterous trade winds for the best offshore sailing.

Antigua is home to the famous Antigua Classics in April and her proliferation of stunning beaches, anchorages and safe ports draws yachts from all over the world.

Sailing Lugger Grayhound racing at Antigua Classics in 2014
Sailing Lugger Grayhound racing at Antigua Classics in 2014

Barbuda - Frigate bird colony & sting rays

Barbuda is a day sail away from Antigua so may be a first stop. Miles of shoal water with brilliant turquoise seas surround this low lying island and endless pale pink sand beaches create a desert island feel to Barbuda. There is a frigate bird colony and if the ship anchors in the shallow waters you may spot sting rays or eagle rays from the deck.  Even better- why not climb aloft to spot the larger marine life like turtles.  

Shallows and reefs make the Barbuda shoreline tricky for navigation
Shallows and reefs keep navigators on their toes in the Caribbean


St Kitts & Nevis - dive bombed by Pelicans

The seperate islands St Kitts and Nevis are the same country. Nevis has a 3000ft peak in the centre and looks like a Sombrero from a distance with trade wind clouds sometimes hanging over the summit. An interesting bit of navigation might be to sail a large tall ship through the Narrows but as this is only 15-20ft deep you may be cruising around the outside ! Charlestown is Nevis's only port with many stone buildings and a restored waterfront. There are pelicans on Nevis and many other islands like Antigua, and you can while away pleasant hours watching them dive.  There is a Nelson museum on Nevis. Tamerind Bay is one of the nicer anchorages on the sheltered side of Nevis.

St Kitts and a fly past by a frigate bird. Photo by Pixabay
St Kitts and a fly past by a frigate bird. Photo by Pixabay

Montserrat - devastated by lava & untouched beauty

In 1995 the volcano erupted on Montserrat and the lava flows destroyed the capital Plymouth.  An island that once had 12 000 inhabitants now seems somewhat empty as many evacuated people have never returned.  On half of the island is starkly barren under tonnes of ash but the North remains untouched, lush anf green.  The volcano is quieting down but is still active, and Radio Montserrat issues volcano  navigation warnings daily.  Currently the ship can anchor off the Northern part of the island and sailing past the southern half of the island is a sober reminder of the power of nature.

Caribbean sunset - Tall Ship, probably Picton Castle

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 for the 10-15 days. Even the time of day and whether the sun it 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 !

Caribbean cocktails, probably involving Rum
Caribbean cocktails, probably involving Rum


Which ship for my adventure?

Barque Lord Nelson is our experienced operator in the Leeward Isles. She doesn't spend every winter in the Caribbean, but has been here regularly, as has her bigger sister ship the three masted barque Tenacious. If you want to explore the Leewards on a square rigger she is your ship. Lord Nelson also sails South from Antigua to explore the Windward Isles. Tenacious has been through whole Caribbean Sea to the Panama Canal to reach the Pacific, as well as taking turns with Tenacious to run winter Caribbean island hopping voyages for crew of all abilities. On Lord Nelson and Tenacious are owned by a British charity and their mission is allow able bodied and disabled crew have active adventures all over the world. 

Three masted schooner Blue Clipper was converted from private yacht to sail training ship in 2017 and has already notched up thousands of ocean miles with Classic Sailing guests. Blue Clipper can accommodate up to 12 guest trainees on board, with 6 twin en-suite cabins, a luxury double cabin, large saloon areas which are beautifully decorated and maintained, a well-equipped galley and plenty of places to sit and relax on deck. Blue Clipper is creating some incredible charter circuits and pioneering new routes. In the Northern Hemisphere she aims to go somewhere hot for the winter, which is likely to feature passage making voyages through the Caribbean where you are joining on one island and returning from another.

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