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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)
9 Day Southern Caribbean Holiday Cruise: British Virgin Islands, Dominica & Grenada with Azamara Cruises
Cruise
 (5)

9 Days (8 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 19 December 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$2,189
Oceanview
$2,749
Balcony
$3,349
Suite
$5,109
From
US$2,189
Per Person
View Trip
9 Day A Journey Of Sparkling Skies & Bright Beginnings with Explora Journeys
Cruise

9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 27 December 2026
Visit: USA, Dominican Republic, Virgin Islands, Saint Kitts and Nevis, Puerto Rico
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$6,800
From
US$6,800
Per Person
View Trip
11 Day A Journey Of Caribbean Charm & Spectacular Natural Beauty with Explora Journeys
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ships: Explora II, Explora I
Departures: Nov 2026 to Nov 2027
Visit: USA, Curacao, Aruba, Colombia, Cayman Islands
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$5,590
From
US$5,590
Per Person
View Trip
12 Day Miami, Fl to Miami, Fl with Silversea
Cruise
 (1)

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Nova
Departure: 18 December 2027
Visit: USA, Virgin Islands, Saint Kitts and Nevis, Guadeloupe, Martinique
All-Inclusive Fare
All-Inclusive Plus Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,900
Suite
$11,500
From
US$6,900
Save 1,500
Per Person
View Trip
13 Day Beach-blessed Isles with Oceania Cruises
Cruise
 (1)

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 10 December 2027
Visit: USA, Bahamas, Dominican Republic, Puerto Rico (+4 more), Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$3,499
Oceanview
$3,799
Balcony
$5,699
Suite
$7,899
From
US$3,499
Save 3,499
Per Person
View Trip
16 Day Broadway To The ABC Islands with Oceania Cruises
Cruise
 (1)

16 Days (15 Nights) New York to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 06 November 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis (+5 more), Bonaire, Curacao, Aruba, Jamaica, Cayman Islands
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$4,199
Oceanview
$4,599
Balcony
$6,999
Suite
$9,599
From
US$4,199
Save 4,199
Per Person
View Trip
15 Day Southern Caribbean Cruise: Dominica, Bequia & Grenada with Azamara Cruises
Cruise
 (5)

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 28 November 2027
Visit: Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis (+8 more), Saint Martin, Virgin Islands, Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago
Azamara Always Included
Inside
$3,649
Oceanview
$4,589
Balcony
$5,709
Suite
$8,779
From
US$3,649
Per Person
View Trip
7 Day Caribbean Sojourn with Emerald Cruises
New ReleaseCruise
 (3)

7 Days (6 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 03 January 2027
Visit: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Saint Martin
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,058
From
US$7,058
Save 347
Per Person
View Trip
17 Day An Extended Journey of Island Energy & Ocean Tranquillity with Explora Journeys
Cruise

17 Days (16 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 13 January 2027
Visit: Puerto Rico, Saint Martin, Guadeloupe, Grenada (+7 more), Saint Lucia, Dominican Republic, USA, Virgin Islands, Anguilla, Martinique, Saint Kitts and Nevis
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$9,720
From
US$9,720
Per Person
View Trip
10 Day Southern Caribbean Cruise: St.barts, Antigua & Tortola with Azamara Cruises
Cruise
 (3)

10 Days (9 Nights) San Juan to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 05 January 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis, USA
Azamara Always Included
Inside
$2,779
Oceanview
$3,449
Balcony
$4,119
Suite
$6,349
From
US$2,779
Per Person
View Trip
8 Day Caribbean Yachting Discovery with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) Saint John's to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departures: Nov 2027 to Mar 2028
Visit: Antigua and Barbuda, Saint Barthelemy, Guadeloupe, Virgin Islands
Preferred Plus Fare + Air Credit
Exclusive Savings
Inside
-
Oceanview
$6,135
Balcony
-
Suite
$7,773
From
US$6,135
Save 640
Per Person
View Trip
10 Day Southern Caribbean Cruise: Grenada, Saint Lucia & Martinique with Azamara Cruises
Cruise
 (5)

10 Days (9 Nights) Bridgetown to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 13 March 2028
Visit: Barbados, Grenada, Saint Lucia, Martinique (+4 more), Dominica, Saint Martin, Virgin Islands, USA
Azamara Always Included
Inside
$2,789
Oceanview
$3,339
Balcony
$4,139
Suite
$6,089
From
US$2,789
Per Person
View Trip
12 Day Miami, Fl to Miami, Fl with Silversea
Cruise
 (1)

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Nova
Departure: 31 January 2028
Visit: USA, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Martinique, Saint Kitts and Nevis, Puerto Rico
All-Inclusive Fare
Inside
-
Oceanview
-
Balcony
$7,700
Suite
$12,100
From
US$7,700
Per Person
View Trip
11 Day Miami to Cartagena with Silversea
Cruise

11 Days (10 Nights) Miami to Cartagena
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 05 January 2028
Visit: USA, Virgin Islands, Saint Barthelemy, Curacao, Bonaire, Colombia
All-Inclusive Fare
Inside
-
Oceanview
$6,000
Balcony
$7,900
Suite
-
From
US$6,000
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
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$3,149
Oceanview
$3,999
Balcony
$4,699
Suite
$6,549
From
US$3,149
Save 3,149
Per Person
View Trip
9 Day Southern Caribbean Cruise: Martinique, Grenada & U.S. Virgin Islands with Azamara Cruises
Cruise
 (5)

9 Days (8 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 06 November 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+4 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados
Azamara Always Included
Inside
$2,229
Oceanview
$2,789
Balcony
$3,389
Suite
$5,149
From
US$2,229
Per Person
View Trip
8 Day Fall For The Caribbean with Regent Seven Seas
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 22 November 2026
Visit: USA, Honduras, Guatemala, Belize, Mexico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,599
Suite
$8,999
From
US$8,599
Save 8,599
Per Person
View Trip
32 Day Loving The Island Life with Oceania Cruises
Cruise
 (1)

32 Days (31 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 21 November 2027
Visit: USA, Mexico, Honduras, Belize (+14 more), Aruba, Curacao, Bonaire, Grenada, Saint Lucia, Guadeloupe, Saint Martin, Bahamas, Dominican Republic, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$8,649
Oceanview
$9,049
Balcony
$13,699
Suite
$18,999
From
US$8,649
Save 8,649
Per Person
View Trip
22 Day Caribbean with Cunard
Cruise
 (13)

22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 27 October 2026
Visit: USA, Turks and Caicos Islands, Curacao, Bonaire (+7 more), Aruba, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Saint Martin, Virgin Islands
Bonus Onboard Credit
Inside
$2,139
Oceanview
$2,419
Balcony
$2,969
Suite
$7,589
From
US$2,139
Per Person
View Trip
13 Day Collector's Caribbean with Oceania Cruises
Cruise
 (3)

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 10 December 2026
Visit: USA, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Martinique, Saint Kitts and Nevis, Saint Martin
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$3,999
Oceanview
$4,849
Balcony
$4,725
Suite
$6,975
From
US$3,999
Save 3,999
Per Person
View Trip
8 Day Classic Caribbean Yacht Harbors with Seabourn
Cruise

8 Days (7 Nights) Bridgetown to Philipsburg
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 11 March 2028
Visit: Barbados, Saint Lucia, Montserrat, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands, Saint Martin
Inside
-
Oceanview
-
Balcony
$4,319
Suite
$7,199
From
US$4,319
Per Person
View Trip
11 Day New Year Exuberance with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 28 December 2027
Visit: USA, Mexico, Guatemala, Belize, Honduras, Jamaica, Cayman Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,999
Suite
$10,399
From
US$9,999
Save 9,999
Per Person
View Trip
10 Day A Journey Through Caribbean Delights & Wildlife Wonders with Explora Journeys
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 19 February 2027
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Anguilla
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$6,225
From
US$6,225
Per Person
View Trip
8 Day Reefs Of The Maya with Oceania Cruises
Cruise
 (1)

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Sirena
Departure: 21 November 2027
Visit: USA, Mexico, Honduras, Belize
Your World Included Credit
Your World Inclusions
Exclusive Savings
Inside
$1,899
Oceanview
$1,999
Balcony
$3,099
Suite
$4,399
From
US$1,899
Save 1,899
Per Person
View Trip
8 Day A Journey of Tropical Spirits & the Colourful Beauty of the Antilles with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 19 December 2027
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Saint Barthelemy, USA
Inside
-
Oceanview
-
Balcony
-
Suite
$4,685
From
US$4,685
Per Person
View Trip
17 Day Caribbean Christmas Cruise: Barbados, St. Lucia & St. Thomas with Azamara Cruises
Cruise
 (3)

17 Days (16 Nights) Bridgetown to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 12 December 2026
Visit: Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis (+8 more), Saint Martin, Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy, Martinique, Saint Vincent, Trinidad and Tobago
Azamara Always Included
Inside
$4,299
Oceanview
$4,559
Balcony
$5,689
Suite
$8,909
From
US$4,299
Per Person
View Trip
15 Day An Extended Journey from Vibrant Shores to Spectacular Scenery with Explora Journeys
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 March 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe (+4 more), Puerto Rico, Saint Barthelemy, Montserrat, Saint Kitts and Nevis
Inside
-
Oceanview
-
Balcony
-
Suite
$7,770
From
US$7,770
Per Person
View Trip
17 Day An Extended Journey Through Ancient Marvels & Glittering Shores with Explora Journeys
Cruise

17 Days (16 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 20 January 2027
Visit: USA, Jamaica, Guatemala, Honduras (+6 more), Belize, Dominican Republic, Saint Martin, Guadeloupe, Saint Kitts and Nevis, Puerto Rico
Sky & Sea
Inside
-
Oceanview
-
Balcony
-
Suite
$7,000
From
US$7,000
Per Person
View Trip
18 Day Eastern & Southern Caribbean Cruise: Grenada, Barbados & Aruba with Azamara Cruises
Cruise
 (5)

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
Inside
$4,729
Oceanview
$5,809
Balcony
$7,139
Suite
$10,859
From
US$4,729
Per Person
View Trip
8 Day A Journey Through Art Deco Wonders & Caribbean Adventures with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 23 December 2027
Visit: USA, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis, Puerto Rico
Inside
-
Oceanview
-
Balcony
-
Suite
$4,745
From
US$4,745
Per Person
View Trip
Results: 211-240 of 507

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