Blue Water Holidays
Blue Water Holidays - ABTA - ATOL - CLIA
Experts in River and Small Ship Cruising Holidays since 2002
01756 706500 +44 1756 706500
Blue Water Holidays - ABTA - ATOL - CLIA
01756 706500
+44 1756 706500

Star Clippers Caribbean Cruises

A tall ship voyage is the perfect way to appreciate the slow pace and natural beauty of the Caribbean, famous for its glorious sailing weather

This winter, escape to your Caribbean paradise on a tall ship voyage under full sail. We offer fabulous itineraries from Barbados, St Maarten, Montego Bay and Balboa on superb five-masted sailing ship Royal Clipper and beautiful Star Flyer.

  • Royal Clipper in St Lucia
  • Star Clipper at sunset in the Caribbean
  • Tobago Cays
  • Bottom Bay, Barbados

About Caribbean Cruises

Explore the stunning Caribbean on the Windward Islands or the Grenadine Islands sailing cruise itineraries. Alternatively, discover the exotic Treasure Islands of the British Virgin Islands, the more southerly Leeward Islands or join Royal Clipper on a voyage under full sail to the beautiful ABC Islands of Aruba, Bonaire and Curacao.

Admire the natural beauty of the Caribbean islands on our unique Caribbean crossing sailing cruise from Montego Bay in Jamaica to Bridgetown in Barbados or transit the famous Panama Canal before heading to the remote San Blas Islands on tall ship Star Flyer.

The ships carry watersports and snorkelling equipment, supported by a water sports team, for use on the sandy beaches or for viewing the colourful Caribbean reef fish. We can book you the perfect holiday, including flights and pre and post cruise stays, as all the itineraries offer the perfect opportunity to add nights before or after your cruise holiday.

Cruise Collection


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

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  • 4 - 6 Nights
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  • Grenadine Islands

    7 Nights - Barbados and back

    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 2018 - Dec
    2019 - Jan, Feb, Mar
    Save up to 20% on Winter 2018/19 PLUS exclusive £50pp on all dates!

    Grenadine Islands Cruise on Royal Clipper Cruise Only
    From £1070pp
    View Full Details

  • Windward Islands

    7 Nights - Barbados and back

    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 2018 - Dec
    2019 - Jan, Feb, Mar
    Save up to 20% on Winter 2018/19 PLUS exclusive £50pp on all dates!

    Caribbean Windward Islands Sailing Cruise on Royal Clipper from Barbados Cruise Only
    From £1070pp
    View Full Details

  • Treasure Islands

    7 Nights - St Maarten and back

    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 2018 - Dec
    2019 - Jan, Feb, Mar
    Save 10% on Winter 2018/19 PLUS exclusive £50pp discount on all dates!

    Treasure Islands Cruise Only
    From £1079pp
    View Full Details

  • Leeward Islands Sailing Cruise

    7 Nights - St Maarten and back

    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 2018 - Dec
    2019 - Jan, Feb, Mar
    Save 10% on Winter 2018/19 PLUS exclusive £50pp discount on all dates!

    Leeward Islands Tall Ship Sailing Cruise Cruise Only
    From £1079pp
    View Full Details

  • Westbound Transatlantic Sailing

    16 Nights - Europe to Caribbean

    Star Clippers Ship - Royal Clipper Choice of Ships

    Re-live the romantic age of sail on one of these Westbound Transatlantic sailing crossings departing from Las Palmas or Lisbon to the Caribbean aboard Royal Clipper or Star Flyer 2018 - Oct, Nov
    2019 - Oct, Nov
    Save 20% on 2019 departure PLUS exclusive £50pp discount on all dates!

    Westbound Transatlantic Sailing Cruise Only
    From £1186pp
    View Full Details

  • Eastbound Transatlantic

    16 Nights - Caribbean to Europe

    Star Clippers Ship - Royal Clipper Choice of Ships

    Enjoy the sailing adventure of a lifetime on one of these superb Eastbound transatlantic sailings departing from Barbados or St Maarten on tall ships Royal Clipper or Star Flyer 2019 - Mar
    Save 20% on 2019 departure PLUS exclusive £50pp discount on all departures!

    Eastbound Transatlantic Cruise Only
    From £1222pp
    View Full Details

  • Caribbean Crossing

    11 Nights - Montego Bay to Bridgetown

    Star Clippers Ship - Royal Clipper Royal Clipper

    Sail from Jamaica to Barbados on board magnificent tall ship Royal Clipper and visit stunning Caribbean islands including historic Antigua, glamorous St Barts and picturesque St Lucia 2018 - Dec
    Save 20% PLUS exclusive £50pp discount!

    Caribbean Crossing Cruise Only
    From £1842pp
    View Full Details

  • Panama Canal to the Caribbean

    14 Nights - Balboa to St Maarten

    Star Clippers Ship - Star Flyer Star Flyer

    This 14-night tall ship sailing holiday includes a transit of the magnificent Panama Canal, visits the historic town of Cartagena and explores the stunning islands of the Caribbean 2018 - Dec
    Save 10% PLUS exclusive £50pp discount!

    Panama Canal to the Caribbean Cruise Only
    From £2398pp
    View Full Details

  • Barbados and Panama

    14 Nights - Barbados to Balboa

    Star Clippers Ship - Star Flyer Choice of Ships

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

    Barbados and Panama Cruise Only
    From £2398pp
    View Full Details

  • ABC Islands and Grenadines

    14 Nights - Barbados and back

    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
    Exclusive £50pp discount!

    ABC Islands and Grenadines View Full Details

Caribbean Highlights


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.

Castries (St Lucia)


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.

Fort-de-France (Martinique)

Grenada (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.


St Barts (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 Barts

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.

Virgin Gorda (British Virgin Islands)

Blue Water Reviews

Exploring Cuba on sailing ship Star Flyer

Tues 17th Mar 2015

Cuba had long been a destination of interest to me with its fascinating history and vibrant culture and what better way to see this amazing country than with a 2-night stay in the country's capital Havana and a 5-night tall ship sailing cruise with Star Clippers.

The combination of both a stay in Havana and a cruise with Star Clippers meant I could spend time appreciating the county's culture, experience the local food and way of life and yet also join a sailing cruise seeing the less populated parts of the country, visiting small towns and idyllic beaches in luxury accommodation with magnificent cuisine.

This itinerary began with a direct flight from London Gatwick, taking around 9hrs and arriving in Havana in the early evening. A transfer was arranged as part of the package booked, along with a stay at The Capri Hotel, in downtown Havana. The hotel, which had been recently renovated, was relatively basic but offered a good standard of 3* accommodation with all the necessary amenities and proved a good base for exploring the city.

I spent my first morning in Cuba seeing what downtown Havana had to offer, marvelling at the beautiful 1960's old American classical cars and visiting Cuba's most prestigious hotel, the Hotel Nacional de Cuba. Built in the 1920's the hotel really is a tremendous relic, retaining many of its original features including rooms that were once occupied by the likes of Frank Sinatra and the Italian-American Mafia.

After a traditional Cuban lunch I took the 4 hour transfer to Cienfuegos where I embarked the Star Flyer for a 5-night cruise.

I have cruised with Star Clippers before in the Mediterranean and one of the things I love about these ships is their size and informality, carrying just 170 passengers the ships are small but with plenty of space and with 70 crew on board you are offered exceptional service.

After a very quick embarkation I was shown to my category 3 cabin on the clipper deck. The cabin was well designed making good use of the space with plenty of storage and had two porthole windows letting in lots of light. The marble bathroom was very nice and the inclusion of toiletries, beach towels and a hair dryer meant I didn't have to worry about bringing these things with me! As a repeat guest I was also greeted with a bottle of champagne and a tray of fruits and chocolates ' a nice touch!

Unpacking done, there was time to spend a couple of hours seeing the sights of Cienfuegos before dinner. It was only a short walk from the ship to the centre of the city, a UNESCO World Heritage listed site which showcased some fine examples of Spanish colonial architecture, a handcraft market and a magnificent fortress.

Havana Classic car in Havana Hotel Nacional de Cuba Pastel coloured houses in Trinidad Vintage car in Trinidad Santisima Trinidad Cathedral Handicraft market in Trinidad Vintage car in Trinidad Punta Frances Beach Punta Frances Beach Cayo Largo Dolphins at Cayo Largo Havana Havana Rum Museum Havana La Bodeguita Del Medio, visited by Ernest Hemmingway in 1942

Dinner with Star Clippers was relatively informal, with guests wearing nice evening clothes (perhaps something similar to clothing worn when dining at a restaurant in the UK), no need for cocktail dresses or jackets and ties. Guests were also free to sit where and with whom they liked, with table sizes ranging between 4 and 8. The food however really was quite a lavish affair with an extensive and always varied menu, from which you chose 5 delicious courses!

After dinner the ship set sail from Cienfuegos and guests were invited on deck to join the sail away party. I don't think it's possible to explain the magic of that moment, as I stood with a glass of champagne in my hand and the crew raised the sails to the tune of Vangelis 1492 and Star Flyer gracefully left port making her way towards Playa Ancon.

After a night under full sail and a nice hearty breakfast from a well stocked buffet we arrived into Playa Ancon where a short tender from the ship took us to a beautiful beach. Although the draw of the beach was almost too much, I decided there was plenty of opportunity to relax later and instead took a taxi to explore the nearby town of Trinidad. The town was about 20 minutes away and cost just 30 Cuba CUC for a return trip (about '25) in one of the vintage American convertibles. The Plaza Major in the centre of Trinidad was home to the picturesque Sant'sima Trinidad Cathedral, as well as a small market and pretty square with a couple of nice bars, where I enjoyed an obligatory Mojito, or two, before it was time to go back to the ship.

Our second day on board the Star Flyer was spent at sea which was a fantastic opportunity to fully relax and really appreciate being on a sailing vessel, watching the crew operate and maintain the ship. Guests were also offered the chance to climb the rigging, something I still couldn't pluck up the courage to do... maybe next time! It was also nice to enjoy a long and leisurely lunch on board, which was served as a buffet with a selection of salads, meats, hot and cold mains and a superb choice of scrumptious deserts.

Magnificent tall ship Star Flyer Afternoon tea on Star Flyer Cat 3 cabin on Star Flyer Cat 3 cabin Champagne and chocolates for repeat guests Dining Room on Star Flyer Raising the sails at sail away Buffet breakfast on board Crew at work on Star Flyer Guests climbing the rigging Ropes on Star Flyer Tropical Bar on Star Flyer

Early the next morning we anchored at Punta France on the Isla de la Juventad and took a 30 minute tender to the shore. The beach here was beautiful with white sands and turquoise waters. Apart from the beach bar vendor there was not a single other soul on this beach, it really was Star Clippers' very own paradise! The day here was spent soaking up the sun and taking part in some water sports (provided from the ship's water sports team)- including snorkelling, kayaking and middle boarding.

The final day on this magnificent cruise was spent at the idyllic island of Cayo Largo where, much like the previous day, there was little else to do other than relax on the white sandy beach, unwind and enjoy the sunshine before heading back to the ship to enjoy afternoon tea and a few farewell cocktails at the Tropical Bar.

The next morning I had to say a very sad farewell to Star Flyer and her crew, who even in the short 5-days had learnt my name and my favourite tipple at the bar. Fortunately this wasn't the end of the holiday though; there was still one more night back in Havana.

After the transfer from Cienfuegos and a quick change for dinner, I set out for an evening at Cuba's oldest and most famous cabaret show, Tropicana. An outdoor tropical setting made a beautiful stage for this extravagant spectacle dating back to 1939, with its fabulous music, mesmerising dancing and exuberant costumes! A truly fantastic evening that also included free flowing Havana rum!

An evening flight on the last day left plenty of time to sleep off the previous evenings rum before taking a tour of Havana with a visit to a Cuban cigar factory and the Havana Rum museum as well as time to explore Old Havana, a UNESCO World Heritage Site. There was also a chance to enjoy one last Mojito, and what better place to do so than at La Bodeguita del Medio, a place visited by Ernest Hemmingway back in 1942, which, apparently, makes the best Mojitos in Cuba.

In summary a truly memorable holiday combining a fantastic cruise, seeing some of the 'real' Cuba whilst still enjoying a relaxing beach holiday and getting some winter sun! Highly recommended.

Review by Jenny, Blue Water Holidays

Blue Water Blog