Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 577 unique cruise itineraries with 787 past traveller reviews from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 831 departures starting between September 2026 and April 2029.
Filter Results
577 Cruises (831 Departures)
577 Cruises (831 Departures)
Departures
Show More...
Duration
6 Days
128 Days
Start & End Cities
Ship Size
Cruise Lines
Show More...
Price
$1,400pp
$203,150pp
Countries
Show More...
New ReleaseCruise

10 Days (9 Nights) Miami to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departures: Feb 2029 to Mar 2029
Visits: USA, Bahamas, Turks and Caicos Islands, Puerto Rico, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
$9,884
Balcony
-
Suite
$12,182
From (Per Person)
A$9,884
Save 4,161
Per Person
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 08 November 2026
Visits: USA, Turks and Caicos Islands, Dominican Republic, Virgin Islands, Saint Barthelemy, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,747
From (Per Person)
A$7,747
Save 158
Per Person
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Departure: 05 December 2026
Visits: Barbados, Saint Vincent, Martinique, Guadeloupe, Saint Barthelemy, Antigua and Barbuda, Saint Lucia
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,644
Suite
$13,132
From (Per Person)
A$6,644
Save 4,656
Per Person
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Oceania
Departure: 11 November 2026
Visits: USA, Cayman Islands, Jamaica, Aruba +5 more, Curacao, Grenada, Barbados, Saint Lucia, Saint Kitts and Nevis
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,977
Suite
$8,712
From (Per Person)
A$5,977
Save 4,173
Per Person
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Ray
Departure: 03 January 2028
Visits: USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Martinique, Saint Kitts and Nevis
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,565
Suite
$16,758
From (Per Person)
A$9,565
Save 2,635
Per Person
Cruise

15 Days (14 Nights) New York to Miami
Cruise Line: Regent Seven Seas
Departure: 04 November 2027
Visits: USA, Bahamas, Dominican Republic, Curacao, Aruba, Jamaica, Cayman Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$18,240
Suite
$20,877
From (Per Person)
A$18,240
Save 2,340
Per Person
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 16 February 2027
Visits: USA, Mexico, Belize, Honduras
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,061
Suite
$6,473
From (Per Person)
A$6,061
Save 7,449
Per Person
Cruise

13 Days (12 Nights) Panama City to Miami
Cruise Line: Oceania
Departure: 19 January 2029
Visits: Panama, Costa Rica, Cayman Islands, Jamaica +4 more, Dominican Republic, Virgin Islands, Puerto Rico, USA
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,804
Suite
$11,673
From (Per Person)
A$6,804
Save 2,176
Per Person
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 19 January 2029
Visits: USA, Virgin Islands, Antigua and Barbuda, Saint Lucia, Dominica
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$14,748
Suite
$15,376
From (Per Person)
A$14,748
Save 2,272
Per Person
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 03 December 2028
Visits: USA, Virgin Islands, Antigua and Barbuda, Saint Lucia, Saint Barthelemy
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$13,064
Suite
$15,024
From (Per Person)
A$13,064
Save 2,236
Per Person
Cruise

22 Days (21 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 15 January 2028
Visits: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis +8 more, Martinique, Grenada, Saint Vincent, Saint Lucia, Antigua and Barbuda, Dominica, Curacao, Bonaire
Exclusive Savings
Inside
-
Oceanview
$12,054
Balcony
$13,916
Suite
$25,480
From (Per Person)
A$12,054
Save 246
Per Person
Cruise

15 Days (14 Nights) New York to Miami
Cruise Line: Oceania
Departure: 28 October 2026
Visits: USA, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis +4 more, Saint Lucia, Grenada, Curacao, Aruba
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,325
Suite
$7,652
From (Per Person)
A$5,325
Save 5,035
Per Person
New ReleaseCruise

9 Days (8 Nights) Saint John's to Bridgetown
Cruise Line: Scenic
Departure: 15 October 2027
Visits: Antigua and Barbuda, Saint Barthelemy, Virgin Islands, Montserrat +5 more, Martinique, Saint Lucia, Saint Vincent, Trinidad and Tobago, Barbados
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,498
Suite
$9,340
From (Per Person)
A$8,498
Save 3,147
Per Person
Cruise

11 Days (10 Nights) Miami to Panama City
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 12 April 2027
Visits: USA, Jamaica, Curacao, Aruba, Colombia, Panama
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$12,284
From (Per Person)
A$12,284
Save 251
Per Person
Cruise

8 Days (7 Nights) Pointe-A-Pitre to Pointe-A-Pitre
Cruise Line: Ponant
Ship: Le Ponant
Departures: Jan 2027 to Mar 2028
Visits: Guadeloupe, Martinique, Saint Vincent, Grenada, Dominica
Exclusive Savings
Inside
-
Oceanview
$10,744
Balcony
$15,312
Suite
$16,486
From (Per Person)
A$10,744
Save 416
Per Person
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 29 November 2026
Visits: USA, Puerto Rico, Saint Barthelemy, Sint Maarten, Virgin Islands, Dominican Republic, Bahamas
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$13,740
Suite
$14,495
From (Per Person)
A$13,740
Save 2,250
Per Person
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania
Departures: Dec 2026
Visits: USA, Mexico, Honduras, Belize
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$2,983
Suite
$4,245
From (Per Person)
A$2,983
Save 3,467
Per Person
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania
Departure: 27 February 2027
Visits: USA, Cayman Islands, Jamaica, Aruba +4 more, Curacao, Bonaire, Dominican Republic, Bahamas
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,298
Suite
-
From (Per Person)
A$8,298
Save 2,212
Per Person
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 07 November 2028
Visits: USA, Virgin Islands, Guadeloupe, Saint Lucia, Dominica, Saint Martin
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$13,417
Suite
$14,681
From (Per Person)
A$13,417
Save 2,243
Per Person
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Departure: 03 January 2027
Visits: Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Montserrat, Saint Kitts and Nevis
Exclusive Savings
Inside
-
Oceanview
$4,150
Balcony
$5,228
Suite
$12,446
From (Per Person)
A$4,150
Save 3,550
Per Person
Cruise

8 Days (7 Nights) Bridgetown to Philipsburg
Cruise Line: Seabourn
Departures: Dec 2026 to Feb 2028
Visits: Barbados, Saint Lucia, Montserrat, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands, Saint Martin
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,006
Suite
$10,989
From (Per Person)
A$5,006
Save 148
Per Person
Cruise

9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 05 November 2027
Visits: USA, Turks and Caicos Islands, Saint Barthelemy, Guadeloupe, Saint Kitts and Nevis, Virgin Islands, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$6,796
From (Per Person)
A$6,796
Save 139
Per Person
Cruise

22 Days (21 Nights) Rio de Janeiro to Miami
Cruise Line: Regent Seven Seas
Departure: 26 February 2028
Visits: Brazil, Saint Lucia, Saint Kitts and Nevis, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$35,269
Suite
$37,180
From (Per Person)
A$35,269
Save 2,651
Per Person
Cruise

23 Days (22 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Departure: 09 November 2026
Visits: USA, Barbados, Trinidad and Tobago, Brazil, Grenada, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$26,819
Suite
$27,368
From (Per Person)
A$26,819
Save 2,471
Per Person
Cruise

15 Days (14 Nights) Singapore to Hong Kong
Cruise Line: Silversea
Ship: Silver Muse
Departure: 14 January 2028
Visits: Singapore, Vietnam, China
Exclusive Savings
Inside
-
Oceanview
$11,172
Balcony
$11,995
Suite
$25,088
From (Per Person)
A$11,172
Save 7,828
Per Person
Cruise

13 Days (12 Nights) Miami to Galveston
Cruise Line: Regent Seven Seas
Departure: 29 November 2028
Visits: USA, Virgin Islands, Saint Kitts and Nevis, Aruba, Jamaica, Cayman Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$14,331
Suite
$16,644
From (Per Person)
A$14,331
Save 2,259
Per Person
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania
Departures: Jan 2029 to Mar 2029
Visits: USA, Mexico, Jamaica, Cayman Islands
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,085
Suite
$6,918
From (Per Person)
A$5,085
Save 2,149
Per Person
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania
Departure: 01 March 2028
Visits: USA, Dominican Republic, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,488
Suite
$10,563
From (Per Person)
A$7,488
Save 2,192
Per Person
Cruise

11 Days (10 Nights) Bridgetown to Philipsburg
Cruise Line: Seabourn
Departure: 18 December 2027
Visits: Barbados, Grenada, Saint Vincent, Martinique +6 more, Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands, Anguilla, Saint Martin
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,055
Suite
$16,287
From (Per Person)
A$8,055
Save 143
Per Person
Cruise

15 Days (14 Nights) New York to Miami
Cruise Line: Regent Seven Seas
Departure: 04 November 2028
Visits: USA, Bahamas, Dominican Republic, Curacao, Aruba, Jamaica, Cayman Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$20,906
Suite
$21,680
From (Per Person)
A$20,906
Save 2,384
Per Person
Results: 271-300 of 577

No trips found. Try adjusting the search filters.