Luxury Caribbean Cruises

Take a look through our impressive Caribbean cruise deals and take your pick. Or if you don’t see anything that you like then make sure you give our award-winning Cruise Concierge team a call and they will work hard to create your perfect getaway.

Find Out More About Cruising to the Caribbean

Showing 30 out of 1449 cruises
Per Person
Total Price
List Grid

Range:

APPLY
Fly Cruise From:
Was £9209pp Now: £8702pp

Caribbean Holiday Tapestry

Miami | Charlotte Amalie | Gustavia | Saint John's | Fort-de-France | Roseau | Basseterre | Nassau | Miami | Key West | Georgetown | Santo Tomás de Castilla | Harvest Caye | Cozumel | Miami

  • 16 Dec 2028
  • 22 Nights
Choose between FREE Wine, Beer & Champagne by the glass with lunch and dinner OR shore excursion credit
Fly Cruise From:
Was £9209pp Now: £8702pp
View cruise Enquire Enquire
REF: OCEANIAVIS281216A
Fly Cruise From:
Was £5159pp Now: £4875pp

Caribbean Yucatn Gems

Miami | Progreso | Cozumel | Roatán Island | Harvest Caye | Georgetown | Miami

  • 19 Dec 2028
  • 9 Nights
Choose between FREE Wine, Beer & Champagne by the glass with lunch and dinner OR shore excursion credit
Fly Cruise From:
Was £5159pp Now: £4875pp
View cruise Enquire Enquire
REF: OCEANIASON281219
Fly Cruise From:
Was £10319pp Now: £9751pp

Festive Antilles Adventure

Miami | Progreso | Cozumel | Roatán Island | Harvest Caye | Georgetown | Miami | Cabo Rojo | Oranjestad | Willemstad | Kralendijk | Castries | Saint John's | Tortola | Miami

  • 19 Dec 2028
  • 23 Nights
Choose between FREE Wine, Beer & Champagne by the glass with lunch and dinner OR shore excursion credit
Fly Cruise From:
Was £10319pp Now: £9751pp
View cruise Enquire Enquire
REF: OCEANIASON281219A
Fly Cruise From:
Was £6999pp Now: £6649pp

A Coral Christmas

Miami | Puerto Plata | San Juan (Puerto Rico) | Charlotte Amalie | Philipsburg | Gustavia | Tortola | Miami

  • 20 Dec 2028
  • 10 Nights
Book now with a 7.5% low deposit* - Ends 8th July
Fly Cruise From:
Was £6999pp Now: £6649pp
View cruise Enquire Enquire
REF: REGENTPRT281220
Fly Cruise From:
Was £6329pp Now: £6139pp

Caribbean Celebration

New York | Tortola | Saint Kitts | Castries | Bridgetown | Sint Maarten | New York

  • 22 Dec 2028
  • 13 Nights

Interest free Monthly Payments from JUST £178pp

Fly Cruise From:
Was £6329pp Now: £6139pp
View cruise Enquire Enquire
REF: CUNARDM901
Fly Cruise From:
Was £7929pp Now: £7691pp

Transatlantic Crossing And Caribbean Celebration

New York | Tortola | Saint Kitts | Castries | Bridgetown | Sint Maarten | New York | Southampton

  • 22 Dec 2028
  • 21 Nights

Interest free Monthly Payments from JUST £223pp

Fly Cruise From:
Was £7929pp Now: £7691pp
View cruise Enquire Enquire
REF: CUNARDM901A
Fly Cruise From:
Was £5424pp Now: £5207pp

Caribbean Yachting Hideaways

San Juan (Puerto Rico) | Vieques | Saint John Island | Great Harbour | Philipsburg | Gustavia | Little Bay | Saint John's

  • 22 Dec 2028
  • 7 Nights
Fly Cruise From:
Was £5424pp Now: £5207pp
View cruise Enquire Enquire
REF: EMERALDE17J221228-1
Fly Cruise From:
Was £12119pp Now: £11634pp

Discover the Yachting Islands of the Caribbean

San Juan (Puerto Rico) | Vieques | Saint John Island | Great Harbour | Philipsburg | Gustavia | Little Bay | Saint John's | Basseterre | Îles des Saintes | Deshaies | Gustavia | Virgin Gorda | Norman Island | San Juan (Puerto Rico)

  • 22 Dec 2028
  • 14 Nights
Fly Cruise From:
Was £12119pp Now: £11634pp
View cruise Enquire Enquire
REF: EMERALD2J17221228-1
Fly Cruise From:
Was £8394pp Now: £7974pp

Caribbean Reverie

Galveston | Progreso | Georgetown | Ocho Rios | Oranjestad | Willemstad | Kralendijk | Saint John's | Charlotte Amalie | Miami

  • 22 Dec 2028
  • 15 Nights
EXCLUSIVE $400 onboard spend* - ONLY when booking with SixStarCruises
Book now with a 7.5% low deposit* - Ends 8th July
Fly Cruise From:
Was £8394pp Now: £7974pp
View cruise Enquire Enquire
REF: REGENTMAR281222
Fly Cruise From:
Was £4824pp Now: £4631pp

Grenadines & Windwards yachting

Bridgetown | Speightstown | Saint Vincent | Kingstown | Port Elizabeth | Mayreau Island | Union Island | Mayreau Island | Union Island | Tobago Cays | Bridgetown

  • 23 Dec 2028
  • 7 Nights
Fly Cruise From:
Was £4824pp Now: £4631pp
View cruise Enquire Enquire
REF: EMERALDE01J231228-1
Fly Cruise From:
Was £4932pp Now: £4734pp

Cruising the Leeward Islands

Philipsburg | Basseterre | Anguilla | Virgin Gorda | Gustavia | Philipsburg

  • 23 Dec 2028
  • 7 Nights
Fly Cruise From:
Was £4932pp Now: £4734pp
View cruise Enquire Enquire
REF: EMERALDE08J231228-1
Fly Cruise From:
Was £12105pp Now: £11620pp

Discover the Pearls of the Caribbean

Philipsburg | Basseterre | Anguilla | Virgin Gorda | Gustavia | Philipsburg | Virgin Gorda | Gustavia | Charlestown | Saint John's | Îles des Saintes | Soufrière | Bridgetown

  • 23 Dec 2028
  • 14 Nights
Fly Cruise From:
Was £12105pp Now: £11620pp
View cruise Enquire Enquire
REF: EMERALD2J02231228-1
Fly Cruise From:
Was £7974pp Now: £7575pp

Celebrate The Caribbean

Miami | Oranjestad | Willemstad | Kralendijk | Scarborough | Kingstown | Fort-de-France | Roseau | Castries | Bridgetown

  • 27 Dec 2028
  • 12 Nights
Book now with a 7.5% low deposit* - Ends 8th July
Fly Cruise From:
Was £7974pp Now: £7575pp
View cruise Enquire Enquire
REF: REGENTGRA281227
Fly Cruise From:
Was £7369pp Now: £6963pp

Southern Caribbean Mosaic

Miami | Cabo Rojo | Oranjestad | Willemstad | Kralendijk | Castries | Saint John's | Tortola | Miami

  • 28 Dec 2028
  • 14 Nights
Choose between FREE Wine, Beer & Champagne by the glass with lunch and dinner OR shore excursion credit
Fly Cruise From:
Was £7369pp Now: £6963pp
View cruise Enquire Enquire
REF: OCEANIASON281228
Fly Cruise From:
Was £5519pp Now: £5215pp

Western Caribbean Wonders

Miami | Key West | Georgetown | Santo Tomás de Castilla | Harvest Caye | Cozumel | Miami

  • 28 Dec 2028
  • 10 Nights
Choose between FREE Wine, Beer & Champagne by the glass with lunch and dinner OR shore excursion credit
Fly Cruise From:
Was £5519pp Now: £5215pp
View cruise Enquire Enquire
REF: OCEANIAVIS281228
Fly Cruise From:
Was £9119pp Now: £8617pp

Classic Caribbean & Canal

Miami | Key West | Georgetown | Santo Tomás de Castilla | Harvest Caye | Cozumel | Miami | Charlotte Amalie | Philipsburg | Basseterre | Willemstad | Oranjestad | Cartagena | Panama City | Cartagena | Panama City

  • 28 Dec 2028
  • 23 Nights
Choose between FREE Wine, Beer & Champagne by the glass with lunch and dinner OR shore excursion credit
Fly Cruise From:
Was £9119pp Now: £8617pp
View cruise Enquire Enquire
REF: OCEANIAVIS281228A
Fly Cruise From:
Was £5324pp Now: £5111pp

Caribbean Yachting Discovery

Saint John's | Basseterre | Îles des Saintes | Deshaies | Gustavia | Virgin Gorda | Norman Island | San Juan (Puerto Rico)

  • 29 Dec 2028
  • 7 Nights
Fly Cruise From:
Was £5324pp Now: £5111pp
View cruise Enquire Enquire
REF: EMERALDE18J291228-2
Fly Cruise From:
Was £12356pp Now: £11861pp

Discover the Yachting Islands of the Caribbean

Saint John's | Basseterre | Îles des Saintes | Deshaies | Gustavia | Virgin Gorda | Norman Island | San Juan (Puerto Rico) | Vieques | Saint John Island | Great Harbour | Philipsburg | Gustavia | Little Bay | Saint John's

  • 29 Dec 2028
  • 14 Nights
Fly Cruise From:
Was £12356pp Now: £11861pp
View cruise Enquire Enquire
REF: EMERALD2J17291228-2
Fly Cruise From:
Was £4824pp Now: £4631pp

Grenadines & Windwards yachting

Bridgetown | Speightstown | Saint Vincent | Kingstown | Port Elizabeth | Mayreau Island | Union Island | Mayreau Island | Union Island | Tobago Cays | Bridgetown

  • 30 Dec 2028
  • 7 Nights
Fly Cruise From:
Was £4824pp Now: £4631pp
View cruise Enquire Enquire
REF: EMERALDE01J301228-1
Fly Cruise From:
Was £4832pp Now: £4638pp

Eastern Caribbean with St. Barths

Philipsburg | Virgin Gorda | Gustavia | Charlestown | Saint John's | Îles des Saintes | Soufrière | Bridgetown

  • 30 Dec 2028
  • 7 Nights
Fly Cruise From:
Was £4832pp Now: £4638pp
View cruise Enquire Enquire
REF: EMERALDE02J301228-1
Fly Cruise From:
Was £6999pp Now: £6649pp

Sunset The Year

Miami | Charlotte Amalie | Saint John's | Pointe-à-Pitre | Gustavia | Tortola | Miami

  • 30 Dec 2028
  • 10 Nights
EXCLUSIVE $400 onboard spend* - ONLY when booking with SixStarCruises
Book now with a 7.5% low deposit* - Ends 8th July
Fly Cruise From:
Was £6999pp Now: £6649pp
View cruise Enquire Enquire
REF: REGENTPRT281230
Fly Cruise From:
Was £5631pp Now: £5405pp

Caribbean Yachting Hideaways

San Juan (Puerto Rico) | Vieques | Saint John Island | Great Harbour | Philipsburg | Gustavia | Little Bay | Saint John's

  • 05 Jan 2029
  • 7 Nights
Fly Cruise From:
Was £5631pp Now: £5405pp
View cruise Enquire Enquire
REF: EMERALDE17J050129-1
Fly Cruise From:
Was £12594pp Now: £12090pp

Discover the Yachting Islands of the Caribbean

San Juan (Puerto Rico) | Vieques | Saint John Island | Great Harbour | Philipsburg | Gustavia | Little Bay | Saint John's | Basseterre | Îles des Saintes | Deshaies | Gustavia | Virgin Gorda | Norman Island | San Juan (Puerto Rico)

  • 05 Jan 2029
  • 14 Nights
Fly Cruise From:
Was £12594pp Now: £12090pp
View cruise Enquire Enquire
REF: EMERALD2J17050129-1
Fly Cruise From:
Was £5177pp Now: £4969pp

Grenadines & Windwards yachting

Bridgetown | Speightstown | Saint Vincent | Kingstown | Port Elizabeth | Mayreau Island | Union Island | Mayreau Island | Union Island | Tobago Cays | Bridgetown

  • 06 Jan 2029
  • 7 Nights
Fly Cruise From:
Was £5177pp Now: £4969pp
View cruise Enquire Enquire
REF: EMERALDE01J060129-1
Fly Cruise From:
Was £5179pp Now: £4971pp

Eastern Caribbean with St. Barths

Bridgetown | Soufrière | Îles des Saintes | Saint John's | Charlestown | Gustavia | Virgin Gorda | Philipsburg

  • 06 Jan 2029
  • 7 Nights
Fly Cruise From:
Was £5179pp Now: £4971pp
View cruise Enquire Enquire
REF: EMERALDE02J060129-2
Fly Cruise From:
Was £15506pp Now: £14885pp

Discover Barbados, Panama & Costa Rica

Bridgetown | Speightstown | Saint Vincent | Kingstown | Port Elizabeth | Mayreau Island | Union Island | Mayreau Island | Union Island | Tobago Cays | Bridgetown | Port Elizabeth | Mayreau Island | Kralendijk | Willemstad | Oranjestad | Santa Marta | Cartagena | San Blas Islands | Panama City

  • 06 Jan 2029
  • 18 Nights
Fly Cruise From:
Was £15506pp Now: £14885pp
View cruise Enquire Enquire
REF: EMERALD2C01060129-2
Fly Cruise From:
Was £11821pp Now: £11348pp

Discover the Pearls of the Caribbean

Bridgetown | Soufrière | Îles des Saintes | Saint John's | Charlestown | Gustavia | Virgin Gorda | Philipsburg | Basseterre | Anguilla | Virgin Gorda | Gustavia | Philipsburg

  • 06 Jan 2029
  • 14 Nights
Fly Cruise From:
Was £11821pp Now: £11348pp
View cruise Enquire Enquire
REF: EMERALD2J02060129-2
Fly Cruise From:
Was £78684pp Now: £74749pp

Eras Of Exploration

Miami | Bridgetown | Santarém | Boca de Valeria | Manaus | Parintins | Alter do Chão | Rio de Janeiro | Santos | Montevideo | Buenos Aires | Punta del Este | Port Stanley | Ushuaia | Punta Arenas | Puerto Chacabuco | Puerto Montt | Valparaiso | Coquimbo | Iquique | Arica | Pisco | Callao | Hangaroa | Fakarava | Rangiroa | Bora-Bora | Huahine | Papeete | Moorea | Papeete | Rarotonga | Aitutaki | Pago Pago | Apia | Vava'u | Savusavu | Dravuni Island | Lautoka | Luganville | Port Vila | Nouméa | Sydney | Brisbane | Airlie Beach | Townsville | Cairns | Darwin | Komodo Island | Lombok | Benoa | Singapore | Port Klang | Georgetown | Langkawi Island | Phuket | Hambantota | Male | Mumbai (ex Bombay) | Dubai | Salalah | Jeddah | Safaga | 'Aqaba | Haifa | Piraeus | Sorrento | Civitavecchia

  • 06 Jan 2029
  • 150 Nights
Book now with a 7.5% low deposit* - Ends 8th July
Fly Cruise From:
Was £78684pp Now: £74749pp
View cruise Enquire Enquire
REF: REGENTMAR290106H
Cruise From:
Was £69350pp Now: £65882pp

Endless Worlds, our 128-day Inaugural World Journey 2029

Dubai | Khasab | Mumbai (ex Bombay) | Goa | Cochin | Male | Colombo | Hambantota | Phuket | Langkawi Island | Singapore | Surabaya | Benoa | Komodo Island | Darwin | Port Moresby | Alotau | Cairns | Airlie Beach | Brisbane | Sydney | Melbourne | Hobart | Milford Sound | Port Chalmers | Christchurch | Wellington | Napier | Tauranga | Auckland | Waitangi | Lautoka | Dravuni Island | Suva | Nuku'alofa | Arutanga | Moorea | Bora-Bora | Huahine | Raiatea | Papeete | Fakarava | Pitcairn Island | Hangaroa | Valparaiso | Coquimbo | Pisco | Lima | Salaverry | Manta | Panama City | Cartagena | Willemstad | Oranjestad | Miami | Ocean Cay | New York | Kings Wharf | Horta | Azores | Lisbon | Cádiz | Barcelona

  • 06 Jan 2029
  • 128 Nights
Save up to 25% PLUS up to £2,600 Explora Credit
Cruise From:
Was £69350pp Now: £65882pp
View cruise Enquire Enquire
REF: EXPLORAEX20290106DXBBCN
Cruise From:
Was £61275pp Now: £58211pp

Endless Worlds, our 108-day Inaugural World Journey 2029

Dubai | Khasab | Mumbai (ex Bombay) | Goa | Cochin | Male | Colombo | Hambantota | Phuket | Langkawi Island | Singapore | Surabaya | Benoa | Komodo Island | Darwin | Port Moresby | Alotau | Cairns | Airlie Beach | Brisbane | Sydney | Melbourne | Hobart | Milford Sound | Port Chalmers | Christchurch | Wellington | Napier | Tauranga | Auckland | Waitangi | Lautoka | Dravuni Island | Suva | Nuku'alofa | Arutanga | Moorea | Bora-Bora | Huahine | Raiatea | Papeete | Fakarava | Pitcairn Island | Hangaroa | Valparaiso | Coquimbo | Pisco | Lima | Salaverry | Manta | Panama City | Cartagena | Willemstad | Oranjestad | Miami

  • 06 Jan 2029
  • 108 Nights
Save up to 25% PLUS up to £2,600 Explora Credit
Cruise From:
Was £61275pp Now: £58211pp
View cruise Enquire Enquire
REF: EXPLORAEX20290106DXBMIA

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.

Caribbean Cruise Deals

Choosing your ideal itinerary can be tricky as this is such a diverse region to explore, but with our equally diverse Caribbean cruise deals, you needn’t worry. Here you will find 7 to 14-day sailings visiting each region, or you can embark on a longer adventure and visit East, West and South, all in one cruise holiday. The choice is completely up to you.

Top 5 places to discover in the Caribbean

  • San Juan - Puerto Rico - Whether you fancy a sunshine-filled beach holiday or want to explore a capital bursting with culture, San Juan offers both.
  • Bridgetown - Barbados - As the capital of Barbados there are plenty of things to do here.
  • Ocho Rios - Jamaica - Your stresses will truly melt away when you arrive in this laid-back port of call.
  • Oranjestad - Aruba - This is a great place to see Dutch colonial architecture, with brightly coloured buildings scattered throughout the city.
  • Castries - St. Lucia - Quite possibly one of our favourite islands in the Caribbean, St. Lucia has a beautiful capital city with plenty to see and do.

Our Award-Winning Service


UK Cruise Awards 2026 Partnership Achievement Award
UK Cruise Awards 2026 Partnership Achievement Award
Luxury Cruise Agency of the Year 2025
Luxury Cruise Agency of the Year 2025
TTG Top 20 Luxury Travel Agents 2025
TTG Top 20 Luxury Travel Agents 2025
Best Workplaces in Travel 2024
Best Workplaces in Travel 2024
TTG Luxury Cruise Agency Of The Year 2024
TTG Luxury Cruise Agency Of The Year 2024
Best Use Of Content 2023
Best Use Of Content 2023
Best Specialist Cruise Agent 2023
Best Specialist Cruise Agent 2023
UK Cruise Awards Winners 2023
UK Cruise Awards Winners 2023
Travel Weekly Large Cruise Agency of the Year 2023
Travel Weekly Large Cruise Agency of the Year 2023
Best Luxury Travel Agent 2022
Best Luxury Travel Agent 2022
Sorry, we have been unable to sign you up to receive our emails. Please use an alternative email address or try again later.
You've added to your wishlist. To view, go to Wishlist

Request a Callback