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 1419 cruises
Per Person
Total Price
List Grid

Range:

APPLY
Fly Cruise From:
Was £5726pp Now: £5496pp

Jewels of the Bahamas

Miami | Andros Town | Eleuthera Island | Staniel Cay | Nassau | Bimini Island | Miami

  • 04 Feb 2029
  • 7 Nights
Fly Cruise From:
Was £5726pp Now: £5496pp
View cruise Enquire Enquire
REF: EMERALDE22J040229-1
Fly Cruise From:
Was £10374pp Now: £9012pp

Tropical Transit

Miami | Georgetown | Cartagena | Puntarenas | Puerto Quetzal | Acapulco | Cabo San Lucas | Ensenada | Los Angeles

  • 07 Feb 2029
  • 16 Nights
Launch Offer - Includes savings of up to 10% - On selected suite grades
Book now with a 7.5% low deposit*
Fly Cruise From:
Was £10374pp Now: £9012pp
View cruise Enquire Enquire
REF: REGENTPRT290207
Fly Cruise From:
Was £6684pp Now: £6349pp

Fete Afloat

Bridgetown | Castries | Fort-de-France | Roseau | Pointe-à-Pitre | Gustavia | Philipsburg | Tortola | Miami

  • 07 Feb 2029
  • 10 Nights
EXCLUSIVE $400 onboard spend* - ONLY when booking with SixStarCruises
Book now with a 7.5% low deposit*
Fly Cruise From:
Was £6684pp Now: £6349pp
View cruise Enquire Enquire
REF: REGENTGRA290207
Fly Cruise From:
Was £5276pp Now: £5064pp

Cruising the Leeward Islands

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

  • 10 Feb 2029
  • 7 Nights
Fly Cruise From:
Was £5276pp Now: £5064pp
View cruise Enquire Enquire
REF: EMERALDE08J100229-1
Fly Cruise From:
Was £6594pp Now: £6330pp

Paradise beaches from the Bahamas to the U.S. Virgin Islands

Miami | Nassau | San Salvador Island | Gordon's Beach | Grand Turk Island | Ponce | Saint John Island | San Juan (Puerto Rico)

  • 11 Feb 2029
  • 9 Nights
Fly Cruise From:
Was £6594pp Now: £6330pp
View cruise Enquire Enquire
REF: EMERALDE27J110229-1
Fly Cruise From:
Was £5276pp Now: £5064pp

Cruising the Leeward Islands

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

  • 17 Feb 2029
  • 7 Nights
Fly Cruise From:
Was £5276pp Now: £5064pp
View cruise Enquire Enquire
REF: EMERALDE08J170229-1
Fly Cruise From:
Was £5734pp Now: £5447pp

Island Rhythms & Revelry

Miami | Charlotte Amalie | Gustavia | Saint John's | Tortola | Miami

  • 17 Feb 2029
  • 9 Nights
Book now with a 7.5% low deposit*
Fly Cruise From:
Was £5734pp Now: £5447pp
View cruise Enquire Enquire
REF: REGENTGRA290217
Fly Cruise From:
Was £6497pp Now: £6237pp

Paradise beaches from USVI to the Bahamas

San Juan (Puerto Rico) | Saint John Island | Ponce | Grand Turk Island | Gordon's Beach | San Salvador Island | Nassau | Miami

  • 20 Feb 2029
  • 9 Nights
Fly Cruise From:
Was £6497pp Now: £6237pp
View cruise Enquire Enquire
REF: EMERALDE27J200229-2
Fly Cruise From:
Was £7019pp Now: £6668pp

Baja Breezes

Los Angeles | Cabo San Lucas | La Paz | Mazatlán | Manzanillo | Puerto Vallarta | Los Angeles

  • 23 Feb 2029
  • 10 Nights
Book now with a 7.5% low deposit*
Fly Cruise From:
Was £7019pp Now: £6668pp
View cruise Enquire Enquire
REF: REGENTPRT290223
Fly Cruise From:
Was £5176pp Now: £4968pp

Eastern Caribbean with St. Barths

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

  • 24 Feb 2029
  • 7 Nights
Fly Cruise From:
Was £5176pp Now: £4968pp
View cruise Enquire Enquire
REF: EMERALDE02J240229-1
Fly Cruise From:
Was £8344pp Now: £7926pp

Cadence Of The Canal

Miami | Cozumel | Harvest Caye | Roatán Island | Puerto Limón | Colón | Puerto Limón | Colón | Cartagena | Ocho Rios | Georgetown | Miami

  • 26 Feb 2029
  • 14 Nights
Book now with a 7.5% low deposit*
Fly Cruise From:
Was £8344pp Now: £7926pp
View cruise Enquire Enquire
REF: REGENTGRA290226
Fly Cruise From:
Was £9247pp Now: £8877pp

Panama Canal transit, Colombia & the Grenadines

Panama City | San Blas Islands | Cartagena | Santa Marta | Oranjestad | Willemstad | Kralendijk | Mayreau Island | Port Elizabeth | Bridgetown

  • 01 Mar 2029
  • 11 Nights
Fly Cruise From:
Was £9247pp Now: £8877pp
View cruise Enquire Enquire
REF: EMERALDE02C010329-1
Fly Cruise From:
Was £6594pp Now: £6330pp

Paradise beaches from the Bahamas to the U.S. Virgin Islands

Miami | Nassau | San Salvador Island | Gordon's Beach | Grand Turk Island | Ponce | Saint John Island | San Juan (Puerto Rico)

  • 01 Mar 2029
  • 9 Nights
Fly Cruise From:
Was £6594pp Now: £6330pp
View cruise Enquire Enquire
REF: EMERALDE27J010329-1
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

  • 03 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5179pp Now: £4971pp
View cruise Enquire Enquire
REF: EMERALDE02J030329-2
Fly Cruise From:
Was £9909pp Now: £8577pp

Pearls, Palapas & Panama

Los Angeles | Cabo San Lucas | Puerto Vallarta | Puerto Quetzal | Puntarenas | Cartagena | Georgetown | Miami

  • 05 Mar 2029
  • 16 Nights
Launch Offer - Includes savings of up to 10% - On selected suite grades
Book now with a 7.5% low deposit*
Fly Cruise From:
Was £9909pp Now: £8577pp
View cruise Enquire Enquire
REF: REGENTPRT290305
Fly Cruise From:
Was £5276pp Now: £5064pp

Cruising the Leeward Islands

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

  • 10 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5276pp Now: £5064pp
View cruise Enquire Enquire
REF: EMERALDE08J100329-1
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

  • 10 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5631pp Now: £5405pp
View cruise Enquire Enquire
REF: EMERALDE17J100329-1
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

  • 12 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5177pp Now: £4969pp
View cruise Enquire Enquire
REF: EMERALDE01J120329-1
Fly Cruise From:
Was £6254pp Now: £5941pp

Basslines & Beaches

Miami | Samaná | Charlotte Amalie | Gustavia | Saint John's | Tortola | Miami

  • 12 Mar 2029
  • 10 Nights
Book now with a 7.5% low deposit*
Fly Cruise From:
Was £6254pp Now: £5941pp
View cruise Enquire Enquire
REF: REGENTGRA290312
Fly Cruise From:
Was £5276pp Now: £5064pp

Cruising the Leeward Islands

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

  • 17 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5276pp Now: £5064pp
View cruise Enquire Enquire
REF: EMERALDE08J170329-1
Fly Cruise From:
Was £5531pp Now: £5309pp

Caribbean Yachting Discovery

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

  • 17 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5531pp Now: £5309pp
View cruise Enquire Enquire
REF: EMERALDE18J170329-2
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

  • 19 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5177pp Now: £4969pp
View cruise Enquire Enquire
REF: EMERALDE01J190329-1
Fly Cruise From:
Was £6889pp Now: £5969pp

The Sea To Seville

Miami | Nassau | Ponta Delgada | Funchal | Cádiz | Barcelona

  • 22 Mar 2029
  • 14 Nights
Launch Offer - Includes savings of up to 10% - On selected suite grades
Book now with a 7.5% low deposit*
Fly Cruise From:
Was £6889pp Now: £5969pp
View cruise Enquire Enquire
REF: REGENTGRA290322
Fly Cruise From:
Was £11611pp Now: £11030pp

Crossing To Spring

Miami | Nassau | Ponta Delgada | Funchal | Cádiz | Barcelona | Palamós | Sète | Monaco | Portofino | Livorno | Civitavecchia

  • 22 Mar 2029
  • 21 Nights
Book now with a 7.5% low deposit*
Fly Cruise From:
Was £11611pp Now: £11030pp
View cruise Enquire Enquire
REF: REGENTGRA290322A
Fly Cruise From:
Was £5176pp Now: £4968pp

Eastern Caribbean with St. Barths

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

  • 24 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5176pp Now: £4968pp
View cruise Enquire Enquire
REF: EMERALDE02J240329-1
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

  • 24 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5631pp Now: £5405pp
View cruise Enquire Enquire
REF: EMERALDE17J240329-1
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

  • 26 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5177pp Now: £4969pp
View cruise Enquire Enquire
REF: EMERALDE01J260329-1
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

  • 31 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5179pp Now: £4971pp
View cruise Enquire Enquire
REF: EMERALDE02J310329-2
Fly Cruise From:
Was £5531pp Now: £5309pp

Caribbean Yachting Discovery

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

  • 31 Mar 2029
  • 7 Nights
Fly Cruise From:
Was £5531pp Now: £5309pp
View cruise Enquire Enquire
REF: EMERALDE18J310329-2
Fly Cruise From:
Was £5053pp Now: £4850pp

Grenadines & Windwards yachting

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

  • 02 Apr 2029
  • 7 Nights
Fly Cruise From:
Was £5053pp Now: £4850pp
View cruise Enquire Enquire
REF: EMERALDE01J020429-1

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