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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 537 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 700 departures starting between January 2026 and April 2028.
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537 Cruises (700 Cruise Departures)
8 Day A Journey Through Balmy Shores & Stirring Scenery with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 05 April 2027
Visit: Puerto Rico, Saint Barthelemy, Montserrat, Saint Kitts and Nevis, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,920
Suite
$4,520
From
US$3,920
Per Person
View Trip
17 Day An Extended Journey through Enchanting Islands & Lush Landscapes with Explora Journeys
Cruise

17 Days (16 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 05 January 2027
Visit: USA, Virgin Islands, Saint Barthelemy, Antigua and Barbuda (+7 more), Saint Kitts and Nevis, Puerto Rico, Saint Martin, Guadeloupe, Grenada, Saint Lucia, Dominican Republic
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$8,400
Suite
$9,800
From
US$8,400
Per Person
View Trip
16 Day An Extended Journey Of Cultural Treasures & Seaside Harmony with Explora Journeys
Cruise

16 Days (15 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 05 December 2026
Visit: USA, Mexico, Guatemala, Belize (+6 more), Honduras, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Martin, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$6,335
Suite
$7,175
From
US$6,335
Per Person
View Trip
11 Day Captivating Island Rhythms with Oceania Cruises
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 13 February 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Saint Martin, Puerto Rico, Dominican Republic, Bahamas
Black Friday Sale + Your World Included
Your World Inclusions
Exclusive Savings
Inside
$3,083
Oceanview
$3,713
Balcony
$4,295
Suite
$6,041
From
US$3,083
Save 3,215
Per Person
View Trip
8 Day Eastern Caribbean with St. Barths with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) Bridgetown to Philipsburg
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Nov 2027 to Apr 2028
Visit: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+4 more), Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Saint Martin
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$4,574
Balcony
-
Suite
$6,272
From
US$4,574
Save 7,173
Per Person
View Trip
15 Day Caribbean Celebration with Cunard
Cruise
 (6)

15 Days (14 Nights) New York to New York
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 19 December 2026
Visit: USA, Virgin Islands, Saint Martin, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis
Inside
$2,899
Oceanview
$3,689
Balcony
$3,699
Suite
$10,203
From
US$2,899
Per Person
View Trip
8 Day Yachtsman's Caribbean with Seabourn
Cruise

8 Days (7 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departures: Dec 2026 to Mar 2027
Visit: Saint Martin, Virgin Islands, Saint Kitts and Nevis, Martinique, Saint Vincent, Grenada, Barbados
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,010
Suite
$7,095
From
US$4,010
Save 89
Per Person
View Trip
8 Day A Journey From San Juan To Miami with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 11 March 2026
Visit: Puerto Rico, Anguilla, Antigua and Barbuda, Saint Martin, Virgin Islands, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,095
Suite
$5,760
From
US$4,095
Per Person
View Trip
8 Day Tropical Retreats with Oceania Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 20 January 2027
Visit: USA, Mexico, Honduras, Belize
Black Friday Sale + Your World Included
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$2,740
Suite
$4,292
From
US$2,740
Save 2,858
Per Person
View Trip
11 Day Leeward & Windward Gems with Oceania Cruises
Cruise
 (1)

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Nautica
Departure: 06 February 2026
Visit: USA, Virgin Islands, Saint Kitts and Nevis, Dominica, Antigua and Barbuda, Saint Martin
Upgrade Your Experience
Your World Inclusions
Exclusive Savings
Inside
$2,550
Oceanview
$2,831
Balcony
-
Suite
-
From
US$2,550
Save 3,448
Per Person
View Trip
14 Day Caribbean Celebration with Cunard
Cruise
 (6)

14 Days (13 Nights) New York to New York
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 21 December 2027
Visit: USA, Saint Kitts and Nevis, Saint Lucia, Barbados, Dominica, Saint Martin
Inside
$2,489
Oceanview
$3,429
Balcony
$3,539
Suite
$8,816
From
US$2,489
Per Person
View Trip
8 Day Sea, Sun & Salsa with Regent Seven Seas
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 20 November 2027
Visit: USA, Belize, Guatemala, Mexico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,063
Suite
$5,259
From
US$5,063
Save 10,235
Per Person
View Trip
13 Day Miami to Bridgetown with Silversea
Cruise

13 Days (12 Nights) Miami to Bridgetown
Cruise Line: Silversea
Ship: Silver Ray
Departure: 07 February 2027
Visit: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis (+7 more), Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Dominica, Martinique, Saint Vincent, Barbados
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,880
Suite
$10,640
From
US$6,880
Save 1,720
Per Person
View Trip
15 Day Heavenly Hideaways with Regent Seven Seas
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 08 December 2027
Visit: USA, Jamaica, Aruba, Curacao (+5 more), Bonaire, Grenada, Saint Vincent, Martinique, Saint Kitts and Nevis
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,668
Suite
$9,138
From
US$7,668
Save 14,930
Per Person
View Trip
8 Day Reefs Of The Maya with Oceania Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sonata
Departure: 11 March 2028
Visit: USA, Mexico, Honduras, Belize
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,471
Suite
$4,877
From
US$3,471
Save 3,627
Per Person
View Trip
8 Day Southern Caribbean Cruise: Antigua, Grenada & Barbados with Azamara Cruises
Cruise
 (3)

8 Days (7 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Nov 2026 to Dec 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$1,609
Oceanview
$2,059
Balcony
$2,623
Suite
$4,136
From
US$1,609
Per Person
View Trip
11 Day Panama, Colombia & Caribbean Islands with Ponant
Cruise
 (1)

11 Days (10 Nights) Colon to Fort-de-France
Cruise Line: Ponant
Ship: Le Bellot
Departure: 08 April 2027
Visit: Panama, Colombia, Holland, Saint Lucia, Guadeloupe, Martinique
Inside
-
Oceanview
-
Balcony
$7,150
Suite
$11,330
From
US$7,150
Per Person
View Trip
8 Day A Journey to Island Rhythms & Tranquil Bahamian Bliss with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departures: Jan 2028 to Jan 2028
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Saint Barthelemy, Bahamas, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,415
From
US$3,915
Per Person
View Trip
18 Day Eastern & Southern Caribbean Cruise: Grenada, Barbados & Aruba with Azamara Cruises
Cruise
 (4)

18 Days (17 Nights) San Juan to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 19 December 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica (+10 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Bonaire, Curacao, Aruba, Dominican Republic, Bahamas, USA
Azamara Always Included
Exclusive Savings
Inside
$4,623
Oceanview
$5,670
Balcony
$6,960
Suite
$10,569
From
US$4,623
Save 106
Per Person
View Trip
8 Day West Indies Island Hopping with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 20 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy
Wave Offer
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$5,303
Balcony
-
Suite
$7,073
From
US$5,303
Save 7,687
Per Person
View Trip
8 Day A Journey Of Soft Sands, Azure Waters & Sun-drenched Shores with Explora Journeys
Cruise

8 Days (7 Nights) Miami to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 14 March 2027
Visit: USA, Turks and Caicos Islands, Antigua and Barbuda, Dominica, Saint Vincent, Barbados
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,480
Suite
$5,165
From
US$4,480
Per Person
View Trip
23 Day Caribbean Intensive Cruise: Sint Maarten, Barbados & Cozumel with Azamara Cruises
Cruise
 (8)

23 Days (22 Nights) Miami to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Onward
Departure: 30 November 2027
Visit: USA, Virgin Islands, Saint Martin, Martinique (+8 more), Saint Lucia, Barbados, Dominica, Saint Kitts and Nevis, Puerto Rico, Mexico, Belize, Honduras
Azamara Always Included
Exclusive Savings
Inside
$5,618
Oceanview
$6,918
Balcony
$8,683
Suite
$12,689
From
US$5,618
Save 121
Per Person
View Trip
8 Day A Journey of Intimate Island Bliss & Caribbean Breeze with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 05 February 2028
Visit: Puerto Rico, Saint Barthelemy, Virgin Islands, Bahamas, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,180
Suite
$4,820
From
US$4,180
Per Person
View Trip
11 Day Golden Caribbean Strands with Oceania Cruises
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 23 February 2027
Visit: USA, Puerto Rico, Saint Kitts and Nevis, Saint Martin, Virgin Islands, Dominican Republic, Bahamas
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
$2,935
Oceanview
$3,711
Balcony
$4,293
Suite
$6,039
From
US$2,935
Save 3,063
Per Person
View Trip
8 Day Yachtsman's Caribbean with Seabourn
Cruise

8 Days (7 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 21 February 2026
Visit: Saint Martin, Virgin Islands, Saint Kitts and Nevis, Martinique, Saint Vincent, Grenada, Barbados
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$11,607
From
US$11,607
Save 224
Per Person
View Trip
8 Day A Journey of Underwater Jewels & Captivating New Year's Eve Celebration with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 26 December 2027
Visit: USA, Dominican Republic, Virgin Islands, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,590
Suite
$6,300
From
US$5,590
Per Person
View Trip
12 Day Leeward Islands & Dominica Dreams with Seabourn
Cruise
 (1)

12 Days (11 Nights) Miami to Miami
Cruise Line: Seabourn
Ship: Seabourn Quest
Departure: 23 November 2027
Visit: USA, Puerto Rico, Saint Barthelemy, Montserrat, Dominica, Saint Kitts and Nevis, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
$4,872
Balcony
$6,018
Suite
$8,841
From
US$4,872
Save 77
Per Person
View Trip
7 Day Splendours of the Caribbean with Emerald Cruises
New ReleaseCruise

7 Days (6 Nights) Saint Thomas to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 03 January 2027
Visit: Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy, Puerto Rico
Wave Offer
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$4,679
From
US$4,679
Save 7,311
Per Person
View Trip
8 Day A Journey Of Blissful Escapes & Island Splendour with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 15 November 2026
Visit: Puerto Rico, Anguilla, Antigua and Barbuda, Virgin Islands, Dominican Republic, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,125
Suite
$4,760
From
US$4,125
Per Person
View Trip
11 Day Bridgetown to Bridgetown with Silversea
Cruise

11 Days (10 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 15 January 2027
Visit: Barbados, Saint Vincent, Grenada, Aruba (+4 more), Curacao, Bonaire, Martinique, Saint Lucia
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,720
Balcony
$5,280
Suite
$4,800
From
US$4,720
Save 1,180
Per Person
View Trip
Results: 241-270 of 537

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