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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 539 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 702 departures starting between January 2026 and April 2028.
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539 Cruises (702 Cruise Departures)
15 Day Los Angeles To Miami with Cunard
Cruise

15 Days (14 Nights) Los Angeles to Miami
Cruise Line: Cunard
Ship: Queen Anne
Departure: 05 April 2026
Visit: USA, Guatemala, Panama, Curacao, Aruba
Inside
$1,689
Oceanview
-
Balcony
$2,909
Suite
$6,067
From
US$1,689
Per Person
View Trip
15 Day Exotic Coasts & Casco Viejo with Regent Seven Seas
Cruise

15 Days (14 Nights) Miami to Panama City
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 23 February 2027
Visit: USA, Mexico, Belize, Honduras (+5 more), Cayman Islands, Jamaica, Costa Rica, Colombia, Panama
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,637
Suite
$10,274
From
US$9,637
Save 16,161
Per Person
View Trip
18 Day A Grand Journey of Bright Coastlines & Captivating Havens with Explora Journeys
Cruise

18 Days (17 Nights) Quebec City to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 15 October 2026
Visit: Canada, USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Martin, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$9,485
Suite
$10,950
From
US$9,485
Per Person
View Trip
27 Day Canada & Caribbean Cruise: Montreal, Quebec & Barbados with Azamara Cruises
Cruise
 (3)

27 Days (26 Nights) Montreal to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 19 October 2026
Visit: Canada, USA, Bermuda, Saint Martin (+8 more), Virgin Islands, Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Exclusive Savings
Inside
$7,464
Oceanview
$7,852
Balcony
$9,598
Suite
$14,933
From
US$7,464
Save 175
Per Person
View Trip
26 Day Montreal to Miami with Silversea
Cruise

26 Days (25 Nights) Montreal to Miami
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 24 October 2026
Visit: Canada, USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Montserrat
All-Inclusive Fare
Inside
-
Oceanview
$9,600
Balcony
$11,800
Suite
$21,100
From
US$9,600
Per Person
View Trip
28 Day East Coast Escapade with Oceania Cruises
Cruise
 (1)

28 Days (27 Nights) Montreal to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 25 October 2027
Visit: Canada, USA, Virgin Islands, Antigua and Barbuda (+6 more), Saint Kitts and Nevis, Bonaire, Curacao, Aruba, Jamaica, Cayman Islands
Black Friday Sale + Your World Included
Your World Inclusions
Exclusive Savings
Inside
$8,568
Oceanview
$9,392
Balcony
$13,369
Suite
$18,607
From
US$8,568
Save 8,930
Per Person
View Trip
17 Day Epic Atlantic Escapade with Regent Seven Seas
Cruise

17 Days (16 Nights) Montreal to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Splendor
Departure: 30 October 2026
Visit: Canada, Sint Maarten, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands, Puerto Rico, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,689
Suite
$13,061
From
US$11,689
Save 18,509
Per Person
View Trip
26 Day Canada & Caribbean Isles with Oceania Cruises
Cruise

26 Days (25 Nights) Montreal to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 17 October 2026
Visit: Canada, USA, Virgin Islands, Antigua and Barbuda (+5 more), Saint Kitts and Nevis, Saint Lucia, Grenada, Curacao, Aruba
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,561
Suite
$16,896
From
US$11,561
Save 12,137
Per Person
View Trip
41 Day Amazon & Tropical Isles with Oceania Cruises
Cruise
 (1)

41 Days (40 Nights) Lisbon to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 09 November 2026
Visit: Portugal, Spain, Puerto Rico, Bahamas (+9 more), USA, Virgin Islands, Antigua and Barbuda, Saint Lucia, Trinidad and Tobago, Brazil, Barbados, Dominica, Saint Martin
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
$9,706
Oceanview
$10,822
Balcony
$15,866
Suite
$21,152
From
US$9,706
Save 10,092
Per Person
View Trip
29 Day Seattle To Miami with Cunard
Cruise
 (13)

29 Days (28 Nights) Seattle to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 17 September 2026
Visit: USA, Canada, Mexico, Guatemala, Panama, Curacao, Aruba
Inside
$2,288
Oceanview
$2,599
Balcony
$2,800
Suite
$7,854
From
US$2,288
Per Person
View Trip
43 Day Miami To Seattle with Cunard
Cruise
 (13)

43 Days (42 Nights) Miami to Seattle
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 02 April 2026
Visit: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia (+8 more), Barbados, Saint Martin, Virgin Islands, Colombia, Panama, Costa Rica, Mexico, Canada
Inside
$3,299
Oceanview
$3,699
Balcony
$4,399
Suite
$11,504
From
US$3,299
Per Person
View Trip
41 Day Seattle To Miami with Cunard
Cruise
 (13)

41 Days (40 Nights) Seattle to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 17 September 2026
Visit: USA, Canada, Mexico, Guatemala (+9 more), Panama, Curacao, Aruba, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Saint Martin, Virgin Islands
Inside
$3,119
Oceanview
$3,919
Balcony
$4,000
Suite
$11,623
From
US$3,119
Per Person
View Trip
30 Day Southampton To Rio De Janeiro with Cunard
Cruise

30 Days (29 Nights) London to Rio de Janeiro
Cruise Line: Cunard
Ship: Queen Anne
Departure: 10 January 2027
Visit: England, Bermuda, USA, Turks and Caicos Islands, Barbados, Brazil
Inside
$4,289
Oceanview
$5,909
Balcony
$6,347
Suite
$14,891
From
US$4,289
Per Person
View Trip
39 Day Barcelona To Miami Grand Voyage with Azamara Cruises
Cruise
 (8)

39 Days (38 Nights) Barcelona to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 06 November 2027
Visit: Spain, Gibraltar, Portugal, Morocco (+9 more), USA, Virgin Islands, Saint Martin, Martinique, Saint Lucia, Barbados, Dominica, Saint Kitts and Nevis, Puerto Rico
Azamara Always Included
Exclusive Savings
Inside
$8,628
Oceanview
$10,588
Balcony
$13,498
Suite
$19,318
From
US$8,628
Save 191
Per Person
View Trip
28 Day A Grand Journey Of Colourful Moroccan Shores & Idyllic Caribbean Scenery with Explora Journeys
Cruise

28 Days (27 Nights) Barcelona to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 21 October 2026
Visit: Spain, Portugal, Morocco, Antigua and Barbuda, Anguilla, Puerto Rico, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$16,615
Suite
$18,740
From
US$16,615
Per Person
View Trip
28 Day Springtime Atlantic Crossing with Regent Seven Seas
Cruise

28 Days (27 Nights) Miami to Barcelona
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 20 March 2028
Visit: USA, Dominican Republic, Puerto Rico, Saint Barthelemy (+8 more), Dominica, Guadeloupe, Saint Kitts and Nevis, Virgin Islands, Bahamas, Portugal, Spain, Morocco
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$14,651
Suite
$16,611
From
US$14,651
Save 24,147
Per Person
View Trip
59 Day Valparaiso To Miami Grand Voyage with Azamara Cruises
Cruise
 (4)

59 Days (58 Nights) Valparaiso to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 24 January 2028
Visit: Chile, Argentina, Antarctica, Falkland Islands (+12 more), Uruguay, Brazil, French Guiana, Trinidad and Tobago, Barbados, Grenada, Saint Lucia, Martinique, Dominica, Saint Martin, Virgin Islands, USA
Azamara Always Included
Exclusive Savings
Inside
$19,740
Oceanview
$21,874
Balcony
$26,433
Suite
$40,294
From
US$19,740
Save 469
Per Person
View Trip
26 Day Los Angeles To Southampton with Cunard
Cruise

26 Days (25 Nights) Los Angeles to London
Cruise Line: Cunard
Ship: Queen Anne
Departure: 05 April 2026
Visit: USA, Guatemala, Panama, Curacao, Aruba, Portugal, England
Inside
-
Oceanview
-
Balcony
$4,419
Suite
-
From
US$4,419
Per Person
View Trip
55 Day Epic Antarctic & Amazon with Oceania Cruises
Cruise
 (1)

55 Days (54 Nights) Valparaiso to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 14 February 2027
Visit: Chile, Argentina, Antarctica, Falkland Islands (+6 more), Uruguay, Brazil, Barbados, Antigua and Barbuda, Virgin Islands, USA
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
$15,043
Oceanview
$16,110
Balcony
$21,203
Suite
-
From
US$15,043
Save 15,655
Per Person
View Trip
91 Day South America Discovery with Cunard
Cruise

91 Days (90 Nights) Hamburg to Hamburg
Cruise Line: Cunard
Ship: Queen Anne
Departure: 05 January 2027
Visit: Germany, Holland, Belgium, England (+13 more), Bermuda, USA, Turks and Caicos Islands, Barbados, Brazil, Uruguay, Argentina, Chile, Peru, Ecuador, Panama, Aruba, Portugal
Exclusive Savings
Inside
$14,191
Oceanview
$19,626
Balcony
$21,626
Suite
$42,961
From
US$14,191
Per Person
View Trip
37 Day Caribbean To Cape Horn with Oceania Cruises
Cruise
 (1)

37 Days (36 Nights) Miami to Buenos Aires
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 19 December 2026
Visit: USA, Curacao, Aruba, Colombia (+7 more), Panama, Ecuador, Peru, Chile, Argentina, Falkland Islands, Uruguay
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
$10,002
Oceanview
$10,633
Balcony
$14,222
Suite
$20,430
From
US$10,002
Save 10,396
Per Person
View Trip
57 Day South America Discovery From Fort Lauderdale with Cunard
Cruise

57 Days (56 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Cunard
Ship: Queen Anne
Departure: 22 January 2027
Visit: USA, Turks and Caicos Islands, Barbados, Brazil (+7 more), Uruguay, Argentina, Chile, Peru, Ecuador, Panama, Aruba
Exclusive Savings
Inside
$11,019
Oceanview
$15,811
Balcony
$17,157
Suite
$35,175
From
US$11,019
Per Person
View Trip
29 Day Caribbean, Central America & Peru Cruise: Aruba, Miami & Panama Canal with Azamara Cruises
Cruise
 (4)

29 Days (28 Nights) Bridgetown to Valparaiso
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 27 December 2027
Visit: Barbados, Bonaire, Curacao, Aruba (+11 more), Dominican Republic, Bahamas, USA, Mexico, Belize, Honduras, Costa Rica, Panama, Ecuador, Peru, Chile
Azamara Always Included
Exclusive Savings
Inside
$8,979
Oceanview
$10,570
Balcony
$12,878
Suite
$18,824
From
US$8,979
Save 210
Per Person
View Trip
58 Day Old & New World Discovery with Oceania Cruises
Cruise
 (1)

58 Days (57 Nights) Venice to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 23 October 2026
Visit: Italy, Croatia, Montenegro, Greece (+14 more), Sicily, Spain, Portugal, Puerto Rico, Bahamas, USA, Virgin Islands, Antigua and Barbuda, Saint Lucia, Trinidad and Tobago, Brazil, Barbados, Dominica, Saint Martin
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
$14,951
Oceanview
$16,212
Balcony
$24,360
Suite
$32,508
From
US$14,951
Save 15,547
Per Person
View Trip
48 Day Footsteps Of Columbus with Oceania Cruises
Cruise
 (1)

48 Days (47 Nights) Barcelona to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 02 November 2026
Visit: Spain, Portugal, Puerto Rico, Bahamas (+9 more), USA, Virgin Islands, Antigua and Barbuda, Saint Lucia, Trinidad and Tobago, Brazil, Barbados, Dominica, Saint Martin
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
$11,961
Oceanview
$13,028
Balcony
$19,285
Suite
$25,832
From
US$11,961
Save 12,437
Per Person
View Trip
78 Day Circle South America Grand Voyage with Azamara Cruises
Cruise
 (4)

78 Days (77 Nights) Miami to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 05 January 2028
Visit: USA, Mexico, Belize, Honduras (+19 more), Costa Rica, Panama, Ecuador, Peru, Chile, Argentina, Antarctica, Falkland Islands, Uruguay, Brazil, French Guiana, Trinidad and Tobago, Barbados, Grenada, Saint Lucia, Martinique, Dominica, Saint Martin, Virgin Islands
Azamara Always Included
Exclusive Savings
Inside
$25,403
Oceanview
$29,613
Balcony
$35,821
Suite
$51,826
From
US$25,403
Save 586
Per Person
View Trip
75 Day Circle South America Grand Voyage with Azamara Cruises
Cruise
 (3)

75 Days (74 Nights) Miami to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 14 January 2027
Visit: USA, Virgin Islands, Saint Martin, Saint Kitts and Nevis (+18 more), Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Barbados, Trinidad and Tobago, French Guiana, Brazil, Uruguay, Argentina, Falkland Islands, Antarctica, Chile, Peru, Panama, Costa Rica, Colombia, Mexico
Azamara Always Included
Exclusive Savings
Inside
$28,068
Oceanview
$29,261
Balcony
$32,763
Suite
$54,908
From
US$28,068
Save 661
Per Person
View Trip
33 Day Around The Americas with Oceania Cruises
Cruise

33 Days (32 Nights) Montreal to Los Angeles
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 10 October 2027
Visit: Canada, Bermuda, Bahamas, USA (+6 more), Cayman Islands, Colombia, Panama, Costa Rica, Guatemala, Mexico
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$12,847
Suite
$21,480
From
US$12,847
Save 13,451
Per Person
View Trip
66 Day Grand South America Mosaic with Regent Seven Seas
Cruise

66 Days (65 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Voyager
Departure: 13 January 2028
Visit: USA, Cayman Islands, Jamaica, Colombia (+12 more), Costa Rica, Panama, Ecuador, Peru, Chile, Antarctica, Falkland Islands, Argentina, Uruguay, Brazil, Saint Lucia, Saint Kitts and Nevis
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$51,107
Suite
$53,214
From
US$51,107
Save 82,891
Per Person
View Trip
Results: 511-539 of 539

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