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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 507 unique cruise itineraries with 805 past traveler reviews from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 670 departures starting between April 2026 and April 2028.
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507 Cruises (670 Cruise Departures)
22 Day An Extended Journey from Majestic Horizons to Mayan Gems with Explora Journeys
Cruise

22 Days (21 Nights) Miami to Los Angeles
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 12 April 2027
Visit: USA, Jamaica, Curacao, Aruba (+5 more), Colombia, Panama, El Salvador, Guatemala, Mexico
Inside
-
Oceanview
-
Balcony
-
Suite
$12,840
From
US$12,840
Per Person
View Trip
12 Day Pristine Islands of the Caribbean & the Panama Canal with Scenic
New ReleaseCruise

12 Days (11 Nights) Bridgetown to Panama City
Cruise Line: Scenic
Ship: Scenic Eclipse I
Departure: 20 October 2027
Visit: Barbados, Saint Lucia, Saint Vincent, Curacao, Colombia, Panama
Select Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,363
Suite
$13,590
From
US$11,363
Save 1,067
Per Person
View Trip
30 Day Holiday Harbors & Hollywood with Oceania Cruises
Cruise

30 Days (29 Nights) Miami to Los Angeles
Cruise Line: Oceania Cruises
Ship: Oceania Sonata
Departure: 06 December 2027
Visit: USA, Aruba, Curacao, Bonaire (+11 more), Grenada, Barbados, Saint Lucia, Guadeloupe, Virgin Islands, Cayman Islands, Colombia, Panama, Costa Rica, Guatemala, Mexico
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$14,249
Suite
$19,899
From
US$14,249
Save 14,249
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
Inside
-
Oceanview
$8,039
Balcony
$9,839
Suite
$15,339
From
US$8,039
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 Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$12,349
Suite
$17,499
From
US$12,349
Save 12,349
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
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$8,749
Oceanview
$9,599
Balcony
$13,699
Suite
$19,099
From
US$8,749
Save 8,749
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
Inside
-
Oceanview
-
Balcony
-
Suite
$9,275
From
US$9,275
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
$15,099
Suite
$16,299
From
US$15,099
Save 15,099
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
Bonus Onboard Credit
Inside
$2,681
Oceanview
$3,024
Balcony
$4,621
Suite
$14,163
From
US$2,681
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 Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
$11,049
Balcony
$16,349
Suite
$22,049
From
US$11,049
Save 11,049
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
Bonus Onboard Credit
Inside
$4,289
Oceanview
$5,909
Balcony
$6,399
Suite
$14,879
From
US$4,289
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
Bonus Onboard Credit
Inside
$3,620
Oceanview
$4,169
Balcony
$6,090
Suite
$14,641
From
US$3,620
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
$19,399
Suite
$21,399
From
US$19,399
Save 19,399
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
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$14,660
From
US$14,660
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
Inside
$19,539
Oceanview
$21,959
Balcony
$25,559
Suite
-
From
US$19,539
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 Included Credit
Your World Inclusions
Exclusive Savings
Inside
$15,999
Oceanview
$16,849
Balcony
-
Suite
$57,949
From
US$15,999
Save 15,999
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
$6,699
Suite
-
From
US$6,699
Per Person
View Trip
29 Day Caribbean, Central America & Peru Cruise: Aruba, Miami & Panama Canal with Azamara Cruises
Cruise
 (5)

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
Inside
$8,779
Oceanview
$10,339
Balcony
$12,599
Suite
$18,419
From
US$8,779
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 Included Credit
Your World Inclusions
Exclusive Savings
Inside
$10,349
Oceanview
$10,999
Balcony
$15,649
Suite
-
From
US$10,349
Save 10,349
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 Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
$16,749
Balcony
$25,299
Suite
$59,549
From
US$16,749
Save 16,749
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 Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
$13,399
Balcony
$20,049
Suite
$26,999
From
US$13,399
Save 13,399
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
Inside
$28,729
Oceanview
$29,959
Balcony
$36,909
Suite
$54,889
From
US$28,729
Per Person
View Trip
78 Day Circle South America Grand Voyage with Azamara Cruises
Cruise
 (5)

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
Inside
$25,989
Oceanview
$30,329
Balcony
$36,729
Suite
$53,229
From
US$25,989
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 Included Credit
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$13,249
Suite
$22,049
From
US$13,249
Save 13,249
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
-
Suite
$70,749
From
US$70,749
Save 70,749
Per Person
View Trip
128 Day Navigate The World with Regent Seven Seas
Cruise

128 Days (127 Nights) Miami to Rome
Cruise Line: Regent Seven Seas
Ship: Seven Seas Splendor
Departure: 11 January 2027
Visit: USA, Mexico, Belize, Honduras (+32 more), Cayman Islands, Jamaica, Costa Rica, Colombia, Panama, El Salvador, Guatemala, French Polynesia, American Samoa, Samoa, Fiji, Vanuatu, New Caledonia, Australia, Indonesia, Singapore, Malaysia, Thailand, Sri Lanka, Maldives, India, Oman, United Arab Emirates, Qatar, Saudi Arabia, Egypt, Jordan, Israel, Cyprus, Greece, Turkey, Italy
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$122,799
From
US$122,799
Save 122,799
Per Person
View Trip
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