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Range: £0 - £5000+

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Cruise Only From:
£6335pp

An Extended Celebration Journey into New Caribbean Dawns

Bridgetown | Scarborough | Martinique | Saint John's | Philipsburg | Tortola | Miami | Great Harbour | Deshaies | Bridgetown

  • 21 Dec 2025
  • 13 Nights
Cruise Only From:
£6335pp
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Cruise Only From:
£3780pp

A Journey of Holiday Festivities and Unwrapping Gifts of Sand and Sun

Miami | Ocean Cay | Charlotte Amalie | Spanish Town | Marigot | San Juan (Puerto Rico)

  • 22 Dec 2025
  • 7 Nights
Cruise Only From:
£3780pp
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Cruise Only From:
£7380pp

An Extended Journey of Caribbean Festivities and West Indies Coastal Wonders

Miami | Ocean Cay | Charlotte Amalie | Spanish Town | Marigot | San Juan (Puerto Rico) | Road Bay | Cruz Bay | Puerto Plata | Key West | Miami

  • 22 Dec 2025
  • 14 Nights
Cruise Only From:
£7380pp
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Cruise Only From:
£3900pp

A Journey from Miami to San Juan

Miami | Great Harbour | Deshaies | Bridgetown | Martinique | Basseterre | San Juan (Puerto Rico)

  • 29 Dec 2025
  • 8 Nights
Cruise Only From:
£3900pp
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Cruise Only From:
£6375pp

An Extended Journey into Shimmering New Dawns and Caribbean Secrets

Miami | Great Harbour | Deshaies | Bridgetown | Martinique | Basseterre | San Juan (Puerto Rico) | Gustavia | Saint John's | Tortola | Road Bay | Miami

  • 29 Dec 2025
  • 15 Nights
Cruise Only From:
£6375pp
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Cruise Only From:
£4050pp

A Journey Savy New Years Celebrations and Caribbean Conviviality

San Juan (Puerto Rico) | Road Bay | Cruz Bay | Puerto Plata | Key West | Miami

  • 29 Dec 2025
  • 7 Nights
Cruise Only From:
£4050pp
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Cruise Only From:
£8030pp

An Extended Journey of Fireworks, Fiestas and Spectacular Shores

San Juan (Puerto Rico) | Road Bay | Cruz Bay | Puerto Plata | Key West | Miami | San Andrés Island | Colón | Bocas del Toro | Puerto Limón | Georgetown | Miami

  • 29 Dec 2025
  • 17 Nights
Cruise Only From:
£8030pp
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Cruise Only From:
Was £8050pp Now: £6720pp

An Extended Journey between Idyllic & Volcanic Isles

Bridgetown | Martinique | Basseterre | San Juan (Puerto Rico) | Gustavia | Saint John's | Tortola | Road Bay | Miami | Cruz Bay | Deshaies | Saint George | Bridgetown

  • 03 Jan 2026
  • 16 Nights
Cruise Only From:
Was £8050pp Now: £6720pp
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Cruise Only From:
£5250pp

A Journey to the Land Bridge Connecting the Americas

Miami | San Andrés Island | Colón | Bocas del Toro | Puerto Limón | Georgetown | Miami

  • 05 Jan 2026
  • 10 Nights
Cruise Only From:
£5250pp
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Cruise Only From:
£9900pp

An Extended Journey from Panama's Gateway to Caribbean Paradise

Miami | San Andrés Island | Colón | Bocas del Toro | Puerto Limón | Georgetown | Miami | Charlotte Amalie | Pointe-à-Pitre | Castries | Little Bay | Cruz Bay | Miami

  • 05 Jan 2026
  • 20 Nights
Cruise Only From:
£9900pp
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Cruise Only From:
£3500pp

A Journey from San Juan to Miami

San Juan (Puerto Rico) | Gustavia | Saint John's | Tortola | Road Bay | Miami

  • 06 Jan 2026
  • 7 Nights
Cruise Only From:
£3500pp
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Cruise Only From:
£7100pp

An Extended Journey through Caribbean Cinematic Paradise

San Juan (Puerto Rico) | Gustavia | Saint John's | Tortola | Road Bay | Miami | Cruz Bay | Deshaies | Saint George | Bridgetown | Little Bay | San Juan (Puerto Rico)

  • 06 Jan 2026
  • 15 Nights
Cruise Only From:
£7100pp
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Cruise Only From:
£3850pp

A Journey from Miami to San Juan

Miami | Cruz Bay | Deshaies | Saint George | Bridgetown | Little Bay | San Juan (Puerto Rico)

  • 13 Jan 2026
  • 8 Nights
Cruise Only From:
£3850pp
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Cruise Only From:
£8250pp

An Extended Journey of Fabled Ports, Volcanic Isles and Soft Sands

Miami | Cruz Bay | Deshaies | Saint George | Bridgetown | Little Bay | San Juan (Puerto Rico) | Gustavia | Tortola | Saint John's | Road Bay | Miami

  • 13 Jan 2026
  • 15 Nights
Cruise Only From:
£8250pp
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Cruise Only From:
£5000pp

A Journey of Miami Magnetism and Lesser Antilles Allure

Miami | Charlotte Amalie | Pointe-à-Pitre | Castries | Little Bay | Cruz Bay | Miami

  • 15 Jan 2026
  • 10 Nights
Cruise Only From:
£5000pp
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Cruise Only From:
£9155pp

An Extended Journey of Island Escapes, Colourful Shores and Tranquil Retreats

Miami | Charlotte Amalie | Pointe-à-Pitre | Castries | Little Bay | Cruz Bay | Miami | Puerto Plata | Kralendijk | Oranjestad | Willemstad | Ocean Cay | Miami

  • 15 Jan 2026
  • 20 Nights
Cruise Only From:
£9155pp
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Cruise Only From:
£6700pp

A Journey from San Juan to Miami

San Juan (Puerto Rico) | Gustavia | Tortola | Saint John's | Road Bay | Miami

  • 21 Jan 2026
  • 7 Nights
Cruise Only From:
£6700pp
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Cruise Only From:
£14150pp

An Extended Journey of Caribbean Inspiration and Island Beauty

San Juan (Puerto Rico) | Gustavia | Tortola | Saint John's | Road Bay | Miami | Charlotte Amalie | Terre-de-Haut | Bridgetown | Martinique | Basseterre | San Juan (Puerto Rico)

  • 21 Jan 2026
  • 15 Nights
Cruise Only From:
£14150pp
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Cruise Only From:
£4950pp

A Journey from Miami to Miami

Miami | Puerto Plata | Kralendijk | Oranjestad | Willemstad | Ocean Cay | Miami

  • 25 Jan 2026
  • 10 Nights
Cruise Only From:
£4950pp
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Cruise Only From:
£8930pp

An Extended Journey to Delightful Island Towns and Tropical Treasures

Miami | Puerto Plata | Kralendijk | Oranjestad | Willemstad | Ocean Cay | Miami | Charlotte Amalie | Pointe-à-Pitre | Castries | Little Bay | Cruz Bay | Miami

  • 25 Jan 2026
  • 20 Nights
Cruise Only From:
£8930pp
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Cruise Only From:
£4000pp

A Journey from Miami to San Juan

Miami | Charlotte Amalie | Terre-de-Haut | Bridgetown | Martinique | Basseterre | San Juan (Puerto Rico)

  • 28 Jan 2026
  • 8 Nights
Cruise Only From:
£4000pp
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Cruise Only From:
£7100pp

An Extended Journey into the Tropical Enchantment of Caribbean Splendour

Miami | Charlotte Amalie | Terre-de-Haut | Bridgetown | Martinique | Basseterre | San Juan (Puerto Rico) | Tortola | Saint John's | Gustavia | Road Bay | Miami

  • 28 Jan 2026
  • 15 Nights
Cruise Only From:
£7100pp
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Cruise Only From:
£7900pp

An Extended Journey into the Caribbean’s Most Desirable Shores

Bridgetown | Martinique | Basseterre | San Juan (Puerto Rico) | Tortola | Saint John's | Gustavia | Road Bay | Miami

  • 02 Feb 2026
  • 10 Nights
Cruise Only From:
£7900pp
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Cruise Only From:
£4750pp

A Journey of Miami Magnetism and Lesser Antilles Allure

Miami | Charlotte Amalie | Pointe-à-Pitre | Castries | Little Bay | Cruz Bay | Miami

  • 04 Feb 2026
  • 10 Nights
Cruise Only From:
£4750pp
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Cruise Only From:
£8750pp

An Extended Journey through Vivacious Charm and Boundless Enchantment

Miami | Charlotte Amalie | Pointe-à-Pitre | Castries | Little Bay | Cruz Bay | Miami | Key West | New Orleans | New Orleans | Progreso | Progreso | Cozumel | Miami

  • 04 Feb 2026
  • 20 Nights
Cruise Only From:
£8750pp
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Cruise Only From:
£3500pp

A Journey from San Juan to Miami

San Juan (Puerto Rico) | Tortola | Saint John's | Gustavia | Road Bay | Miami

  • 05 Feb 2026
  • 7 Nights
Cruise Only From:
£3500pp
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Cruise Only From:
£7800pp

A Grand Journey Through Caribbean Serenity and Tropical Treasures

San Juan (Puerto Rico) | Tortola | Saint John's | Gustavia | Road Bay | Miami | Puerto Plata | Roseau | Bridgetown | Basse-Terre | Cruz Bay | San Juan (Puerto Rico)

  • 05 Feb 2026
  • 15 Nights
Cruise Only From:
£7800pp
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Cruise Only From:
£4850pp

A Journey of Latin Flair, Natural Beauty & Vibrant History

Miami | Puerto Plata | Roseau | Bridgetown | Basse-Terre | Cruz Bay | San Juan (Puerto Rico)

  • 12 Feb 2026
  • 8 Nights
Cruise Only From:
£4850pp
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Cruise Only From:
£4950pp

A Journey Bridging the Big Easy and Mystical Ancient Maya

Miami | Key West | New Orleans | New Orleans | Progreso | Progreso | Cozumel | Miami

  • 14 Feb 2026
  • 10 Nights
Cruise Only From:
£4950pp
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Cruise Only From:
£14865pp

An Extended Journey through Timeless Mysteries and Modern Marvels

Miami | Key West | New Orleans | New Orleans | Progreso | Progreso | Cozumel | Miami | Charlotte Amalie | Great Harbour | Saint John's | Gustavia | San Juan (Puerto Rico)

  • 14 Feb 2026
  • 17 Nights
Cruise Only From:
£14865pp
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Prices are subject to change and availability. Prices may vary depending on the airport selected. Promotions are only applicable to select cabin grades, please call for details.

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This website will provide you with information on the financial protection that applies in the case of each holiday and travel service offered before you make your booking. At the time of booking, our Cruise Concierge will also confirm the financial protection applicable to your specific holiday. Please ask us for further information should you require it. The flight inclusive holidays on this website are financially protected by the ATOL scheme. But ATOL protection does not apply to all holiday and travel services listed on this website. If you do not receive an ATOL Certificate then the booking will not be ATOL protected. If you do receive an ATOL Certificate but all parts of your trip are not listed on it, those parts will not be ATOL protected. The cruise-only holidays on this website are financially protected by ABTA. Please see our booking terms and conditions for further information or for more information about financial protection and the ATOL Certificate, click here. SixStarCruises acts as a retail agent to you and also as a disclosed agent of the holiday provider (the Organiser of the holiday). The Foreign & Commonwealth Office have up-to-date advice on staying safe and healthy abroad. Visit the foreign travel advice site for the latest travel updates.

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