Caribbean and Cuba Sailing Cruises

Caribbean and Cuba

All of our Star Clippers Carribean and Cuba cruises are shown below. Tick the boxes to filter by date, ship and duration.


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    • Star Clippers Ship - Royal Clipper
      Royal Clipper
      • Explore the spice island of Grenada and uninhabited Tobago Cays on this sailing voyage to the Grenadine Islands on superb tall ship Royal Clipper

      • Sailing
      • 2017 - Dec
        2018 - Jan, Feb, Mar

    • Save up to 20% on Winter 2017/18 PLUS exclusive £50pp discount on all dates!

    • Star Clippers Ship - Royal Clipper
      Royal Clipper
      • Explore the idyllic Windward Islands on this sailing voyage on magnificent tall ship Royal Clipper visiting picturesque St Lucia, historic Antigua and the chic capital of Martinique

      • Sailing
      • 2017 - Dec
        2018 - Jan, Feb, Mar

    • Save up to 20% on Winter 2017/18 PLUS exclusive £50pp discount on all dates!

    • Star Clippers Ship - Star Flyer
      Star Flyer
      • A fascinating sailing holiday from St Maarten to the unspoilt British Virgin Islands including stunning beaches at Virgin Gorda and Jost Van Dyke, plus rainforested St Kitts and glamorous St Barts

      • Sailing
      • 2018 - Feb, Mar

    • Save 10% on 2018 PLUS exclusive £50pp discount on all dates!

    • Star Clippers Ship - Star Flyer
      Star Flyer
      • Explore the exotic Iles des Saintes, sophisticated St Barts and colonial Antigua on this relaxing Leeward Islands sailing holiday from St Maarten

      • Sailing
      • 2018 - Feb, Mar

    • Save 10% on 2018 PLUS exclusive £50pp discount on all dates!

    • Star Clippers Ship - Star Flyer
      Star Flyer
      • Enjoy overnight stops in the lively cities of Havana and Cienfuegos, and explore the sun-kissed Cayman Islands, on this relaxing voyage under full sail on tall ship Star Flyer

      • Sailing
      • 2017 - Dec
        2018 - Jan

    • Save 10% PLUS exclusive £50pp discount!

    • Star Clippers Ship - Star Flyer
      Star Flyer
      • A sailing holiday from Barbados with a transit of the magnificent Panama Canal visiting the Grenadines, the World Heritage Site of Cartagena and the remote San Blas islands

      • Sailing
      • 2017 - Nov

    • Save 10% on 2017 PLUS exclusive £50pp discount on all dates!

    • Star Clippers Ship - Royal Clipper
      Royal Clipper
      • Join Royal Clipper on this relaxing voyage under full sail visiting the beautiful islands scattered off the coast of Venezuela, the idyllic ABC Islands of Aruba, Bonaire and Curacao and the picture-postcard Grenadines

      • Sailing
      • 2018 - Mar, Apr

    • Save 10% on 2018 PLUS exclusive £50pp discount on all dates!

Explore the beautiful Caribbean islands on a superb sailing cruise on board Royal Clipper or Star Clipper. Visit the smaller islands and ports of the Caribbean that larger ships cannot reach on board these iconic, unique tall sailing ships. Renowned for its glorious sailing weather, every Caribbean itinerary promises the thrill of a voyage under full sail – the ideal way to discover the palm-fringed white sand beaches, colourful towns, picturesque waterfalls and relaxed atmosphere of the Caribbean.

Royal Clipper sails from Barbados to the gloriously untouched Spice Islands of the Grenadines, the diving paradise of Tobago Cays, the French Caribbean island of Martinique, and St Lucia, famous for its lush hills, coconut palms and beautiful waterfalls. Or discover the yachting paradise of Antigua and the verdant rainforests and orchids of Dominica on the Windward Islands voyage.

Sailing cruises to the chic British Virgin Islands take in the Iles de Saintes, ideal for exploring from Royal Clipper’s watersports platform, on the way to discover the excellent beaches and natural pools of Virgin Gorda, and Norman Island, inspiration for Robert Louis Stevenson’s Treasure Island.

Star Clipper sails from St Maarten on the Treasure Islands and Leeward Islands voyages, visiting the most exclusive jewels of the Caribbean; colourful Basseterre on St Kitts with its old plantation houses and St Barts with opportunities for duty-free shopping in exquisite boutiques and people-watching on beautiful beaches.

Discover the colourful and unique island of Cuba on board Star Flyer. Sail from Cienfuegos to colonial cities, UNESCO World Heritage Sites, superb diving at Cayo Blanco and enjoy a visit to the Cayman Islands. Extend your cruise with a stay in historic Havana - ask for details.

Download Star Clipper Cruises 2014/2015 Brochure

  • Dominica
  • Star Clippers Crew
  • Le Soufriere on St Vincent
  • Enjoy the Caribbean beaches
  • St Maarten
  • Royal Clipper towers above Marigot Bay, St Lucia
  • English Harbour, Antigua
  • Star Clipper
  • St Kitts
  • Tourist boat near the Pitons, St Lucia
  • Tobago Cays
  • Fort de France, Martinique

Book any Star Clippers cruise and save an extra £50pp with our exclusive Blue Water Holidays discount! Not combinable with any other offer.

The three Star Clippers ships offer Western Med or Eastern Med sailing cruises in the summer, with Caribbean and Cuba sailing cruises in the winter. New for winter 2016/17 are exciting Thailand, Malaysia and Singapore sailings. Transatlantic crossings travel between Europe and the Caribbean in late Spring and Autumn.

Highlights of a Caribbean Sailing Cruise

Anguilla Anguilla is only 17 miles long, but has 12 miles of lovely, fine sand beaches, beach bars, art galleries, plenty of restaurants and a host of water-sports activities. The island manages to mix glamour with tradition; along the coast are brightly-painted clapboard shacks and luxurious villas.
Antigua St John’s is Antigua’s main port and capital, and is one of the Lesser Antilles’ most developed cities. It is well-known for its malls and boutiques, and the Antigua Rum Distillery, the only one on the island. At the entrance to the harbour is Fort James, built by the British in the 18th century. Within reach is the historic Nelson’s Dockyard at Falmouth Harbour, where he served as a captain aboard HMS Boreas in his youth.
Barbados Bridgetown has a British flavour and its sights include the Parliament Buildings which sit on what was once known as Trafalgar Square, and a huge baobab tree said to have come from Guinea in the 1730s. St Nicholas Abbey in St Peter and Drax Hall in St George are Jacobean buildings with Dutch gables and coral-stone finials. For beaches, bars, restaurants and clubs, make for the south or the Gold Coast to the west.
Bequia Bequia belongs to the Windward Islands and is the second-largest of the chain. It is famous for its open-backed taxis which take visitors on island tours. Beyond Port Elizabeth are small fishing villages, green meadows and quiet beaches. Attractions include Hamilton Fort, the Spring Plantation and its ruined sugar mill, and the OldHegg Turtle Sanctuary at Park Beach.
Dominica Dominica is rich in natural beauty, with waterfalls, rivers, tropical rainforest and numerous rare plants and wildlife. Some of the most popular sights include Emerald Pool, Trafalgar Falls and the World Heritage Site of Morne Trois Pitons Park, a volcanic region with some of the world's largest boiling mud ponds. Offshore, nature lovers might spot up to six species of dolphin, and perhaps killer or humpback whales.
Grenada The 'Spice Island' of Grenada has rainforests, waterfalls and a mountainous interior dotted with cocoa and banana plantations. The shore is a winding series of white and black sand beaches edged with rich vegetation. Carenage is the old harbour area of St George’s where you can see the casting of the famous ‘Christ of the Deep’ statue and watch wooden schooners unload their cargo. For shopping, make for Grand Anse. St George’s has narrow lanes, a busy marketplace and two hill-top forts.
Guadeloupe Guadeloupe consists of two main islands, but also encompasses the Iles des Saintes to the south. The two islands are connected by a mangrove swamp, and there are surfing schools and beach bars along the coastline, plus the Jacques Cousteau Underwater Reserve at Bouillante and Pigeon Islands. French in character, there are numerous good restaurants on Guadeloupe.
Iles des Saintes Les Saintes consists of eight tiny islands. Only two are populated and Terre-de-Haut, as a part of Gaudeloupe, has a leisurely, French atmosphere. In the small village of Bourg there are brightly-painted houses, an art gallery and an outdoor café. There are several watersports on offer, and Pain de Sucre is a favourite spot for swimming and snorkelling.
Jost van Dyke Once the hideaway for a Dutch pirate of the same name, the tiny island of Jost van Dyke welcomes visitors with first-rate hiking trails and some of the best beaches in the British Virgin Islands. It is known to travellers as ‘barefoot’ island for its relaxed atmosphere and laid-back beach bars. The famous Foxy's Tamarind Bar is situated in Great Harbor.
Martinique Fort-de-France is the sophisticated capital of Martinique, and has narrow lanes and Savane Park. Clement House is an old plantation with a rum factory in the grounds offering tastings. For people-watching, take coffee along the capital's Boulevard Allegre, and for good views, go to the Caravelle Peninsula, the site of a ruined chateau.
Norman Island Norman Island is thought to have been the inspiration for Robert Louis Stevenson’s ‘Treasure Island’. In 1750 the crew of a Spanish galleon mutinied, and numerous chests of silver coins were buried on the island before being retrieved by nearby islanders. It is now uninhabited but there is a shore-side restaurant and a cave system with excellent snorkelling.
Nevis This small island is dominated by the extinct 3000-ft volcano of Mount Scenery. The remains of an old sugar plantation are a pleasant place for a stroll, and others have been turned into charming inns. The landscape is rich and green and is home to green vervet monkeys. There is a well-planted Botanical Garden on the island.
Tortola Tortola is the largest of the British Virgin Islands and its port is Road Town, spread around a horseshoe bay. The focus of activity on Tortola is relaxation, and places of interest include the attractive yachting harbour of Soper’s Hole, where Blackbeard lived in the 1700s; the rainforest of Mount Sage National Park, and the Callwod Rum Distillery. The interior is crossed by rugged mountains, and there are numerous beaches.
St Barts Also known as St Barthelemy, St Barts is picturesque, elegant and sophisticated. This volcanic island is rocky and edged with reefs and golden beaches. In the small capital of Gustavia, there is a French ambience, with upmarket boutiques, good French restaurants and duty-free shopping. For swimming, go to the white sand bay of Flamands shaded by lantier palms.
St Kitts Basseterre is the capital of St. Kitts, overlooked by the 17th-century fort at Brimstone Hill and a backdrop of rich green hills inhabited by monkeys. The town has a number of Georgian buildings, and the Circus, a miniature version of Piccadilly. St Kitt’s has the last narrow-gauge railway in the West Indies, taking tourists on a scenic journey round the island from Basseterre.
St Lucia The landscape of St Lucia is a mixture of tropical flowers, rainforest and the dramatic peaks of the Pitons near Soufriere. Beaches include Anse de Sable, Anse Chastenet and Cas en Bas, and in Rodney Bay is the brig Unicorn, used in the film 'Pirates of the Caribbean'. Whales are often seen off the coast. Pigeon Island is linked to St Lucia by a causeway, and is one of the venues for the annual Saint Lucia Jazz Festival.
St Maarten St Martin’s territory is shared by two countries, France and the Netherlands. Marigot is the capital of the French portion, and has smart duty-free boutiques and gourmet restaurants, overlooked by 18th-century Fort St Louis. The capital of the Netherland Antilles region is Philipsburg, which has a warren of narrow streets, courtyard cafés, and traditional West Indian ‘gingerbread’ houses at Wathey Square. St Maarten also offers the 12-metre America’s Cup Challenge aboard America’s Cup Race Boats.
Tobago Cays The idyllic Tobago Cays are five small uninhabited islands which are now part of a protected Marine Park and include a lagoon protected from sea swells by Horseshoe Reef. The vivid colours of the coral and marine life make this a spectacular place for snorkelling and diving, and there are also many turtles and large bird colonies and a World War I wreck of a British gunship.
Virgin Gorda The 'Baths' are Virgin Gorda's unique water grottos formed long ago by ancient lava flows. Huge boulders lie scattered around the natural pools, popular for swimming or soaking. Virgin Gorda is also home to Little Dix Bay, the Bitter End Yacht Club and some excellent beaches.
Martinique St Barts St Lucia Virgin Gorda

Caribbean Treasure Islands Sailing Cruise on Star Clipper

Travel under sail between unspoilt islands on Star Clipper, in the footsteps of the pirates of the Caribbean. This is our diary of a Treasure Islands sailing cruise.

Mon 18th Nov 2013

This was our fourth Star Clippers cruise. The others were in the Mediterranean, and this time it was the Caribbean at Christmas-time. We were looking forward to warm sunny days, superb sailing conditions, and particularly the British Virgin Islands, famous for links to the real pirates, idyllic scenery and a laid-beck style. We were not disappointed.

Our Treasure Islands cruise on Star Clipper started in St Maarten, the Dutch side of the island shared with the French St Martin. We chose to fly via Paris, taking the daily Air France A340 direct to St Maarten. The landing there is subject of many videos on YouTube as the plane heads in just over the beach at the end of the runway!


A short taxi ride from the aiport and we were at the St Maarten cruise terminal in Phillipsburg. We could soon see the masts of Star Clipper amongst the large cruise liners – 170 passengers compared with about 8,000 on the other ships! After a welcome Caribbean punch and a snack we explored our cabin before going up on deck to enjoy the last rays of the day’s sun.

Lifeboat drill preceded dinner – well up to the Star Clippers standard, before going back on deck for the sailaway. Unlike other ships, Star Clipper actually sailed away, the crew hoisting the sails accompanied by the Star Clippers theme music by Vangelis. Once out of port we sailed silently through the moonlit seas, the stars shining in the darkness, the only noise coming from the bow cutting through the water – authentic tall ship sailing at its best.

Raising the sails The beach and bar at Anguilla The ship's watersports equipment at Anguilla Anguilla local restaurant Relaxing on deck Moored at Virgin Gorda The famous Baths at Virgin Gorda Hire yachts off the Baths at Virgin Gorda Boulders stretch inland from the Baths at Virgin Gorda View over Virgin Gorda and the BVI Barbecue at Prickly Pear Beach, Virgin Gorda


Our first call was Anguilla, a British overseas territory, reputed to have the best beaches in the Caribbean. The Star Clippers sports team were active here, taking the ship’s sailing dinghies and swim gear ashore to the sandy beach a short stroll from the atmospheric small village. The beach bar featured a live jazz band, and was decorated with pictures of famous jazz players. A very congenial stop for the less-energetic!


Overnight we headed north to the British Virgin Islands, and passing Sir Richard Branson’s private island of Neckar we sailed in to Virgin Gorda, mooring opposite Prickly Pear beach a short distance from the Bitter End yacht marina. We chose an excursion to the famous Baths of Virgin Gorda, massive boulders strewn across a sandy beach and the nearby land. The scenic drive to the Baths took us up and down steep hills with superb views over Virgin Gorda and the BVI. We did not return directly to the ship, the tender instead taking us to Prickly Pear beach where the ship’s chefs and waiters organised a superb lunchtime beach barbecue. There was time to visit the marina complex at Bitter End before returning to Star Clipper.

Star Clipper under sail Norman Island - the reputed Treasure Island Buffet lunch in the Tropical Bar Tortola - houses with a sea view Soper's Hole, Tortola Lowering the sails View of the setting sun from Star Clipper Heading to Jost van Dyke Wet landing at Jost van Dyke The Soggy Dollar Bar at Jost van Dyke Star Clipper moored off Jost van Dyke


The next day featured sailing down the Sir Francis Drake channel through the heart of the BVI. We called at Norman Island, reputedly the pirate headquarters and home to a lost stash of buried treasure, and allegedly the inspiration for the book Treasure Island, before sailing past Tortola and its capital Road Town to the famous yachting harbour of Soper’s Hole on the north west coast. Arriving there at dusk, we tendered ashore after dinner to explore the marina, shops and attractions of Sopers’s Hole.


Next morning we set sail for Jost van Dyke, the laid-back ‘barefoot’ island. Here was a ‘wet landing’ from the tender, steeping ashore on the beach in ankle-deep water with a helping hand from the sports team. This idyllic setting is home to the ‘Soggy Dollar Bar’ whose ‘Painkiller’ rum cocktail is justly famous! Probably our favourite location, we spent a happy few hours here soaking up the sun, dabbling in the warm seawater, and soaking up the occasional Painkiller.

Heading for the Caribbean island The tender awaits at St Kitts Colonial reminders at St Kitts The centre of St Kitts Star Clipper sailing away Varnished rope blocks drying in the sun The harbour at St Bart's Yachts moored outside St Bart's harbour Eclipse - one of Roman Abramovich's yachts Anchored off St Bart's at night Docked back at St Maarten


Leaving the small islands of the BVI behind, we headed south overnight to St Kitts, a typical Caribbean island with a central cloud covered rainforested peak. There are still traces of its British colonial past, and its town centre clock-roundabout is allegedly modelled on Piccadilly Circus – although rather smaller. The island is visited by large cruise ships, and there are pierside shopping malls designed for their day-trippers.


Our final call was at St Barts, in the French West Indies. We were aware it was frequented by the rich and famous, but nothing prepared us for the massed yachts outside and inside the harbour – those outside too big for the harbour, and topped by Eclipse, one of Roman Abramovich’s yachts, with its two helicopters, and allegedly an anti-missile shield and mini-sub escape vehicle. St Barts itself was an interesting mixture of traditional French Caribbean influences and designer brand shops catering for the luxury market.

The last evening brought the traditional waiter’s parade before sailing at 10pm from St Barts past the rows of luxury yachts.


Our arrival in St Maarten the next morning found us surrounded by ranks of cruise ships – all too big for most of the islands we had visited.


We agreed this was our favourite Star Clippers cruise, and certainly the most relaxing and with the best sailing. It was definitely a recommended way to visit the Caribbean!