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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 Wonders of the Caribbean with Ponant
Cruise
 (1)

8 Days (7 Nights) Fort-de-France to Fort-de-France
Cruise Line: Ponant
Ship: Le Bougainville
Departures: Dec 2026 to Jan 2027
Visit: Martinique, Antigua and Barbuda, Virgin Islands, Saint Barthelemy, Guadeloupe
Inside
-
Oceanview
-
Balcony
$5,060
Suite
$7,560
From
US$5,060
Per Person
View Trip
12 Day Miami, Fl to Miami, Fl with Silversea
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 14 March 2028
Visit: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,400
Balcony
$5,040
Suite
$10,100
From
US$4,400
Save 1,100
Per Person
View Trip
8 Day A Journey Through Caribbean Gems & Multi-coloured Coasts with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 13 December 2026
Visit: Puerto Rico, Anguilla, Antigua and Barbuda, Saint Kitts and Nevis, Turks and Caicos Islands, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,850
Suite
$4,445
From
US$3,850
Per Person
View Trip
16 Day Southern Caribbean Cruise: Dominica, Bequia & Grenada with Azamara Cruises
Cruise
 (4)

16 Days (15 Nights) Bridgetown to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 12 December 2027
Visit: Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis (+7 more), Saint Martin, Virgin Islands, Puerto Rico, Antigua and Barbuda, Saint Vincent, Grenada, Trinidad and Tobago
Azamara Always Included
Exclusive Savings
Inside
$3,844
Oceanview
$4,824
Balcony
$5,978
Suite
$9,179
From
US$3,844
Save 85
Per Person
View Trip
7 Day Eastern Caribbean Cruise: St.lucia, Dominica & St.kitts with Azamara Cruises
Cruise
 (3)

7 Days (6 Nights) Bridgetown to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 12 December 2026
Visit: Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin, Puerto Rico
Azamara Always Included
Inside
$1,399
Oceanview
$1,789
Balcony
$2,273
Suite
$3,583
From
US$1,399
Per Person
View Trip
15 Day Caribbean Cruise: San Juan, Antigua & Barbados with Azamara Cruises
Cruise
 (3)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 21 November 2026
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+9 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin, Saint Barthelemy
Azamara Always Included
Exclusive Savings
Inside
$3,599
Oceanview
$3,773
Balcony
$4,869
Suite
$7,556
From
US$3,599
Save 80
Per Person
View Trip
15 Day Discover the Pearls of the Caribbean with Emerald Cruises
Cruise
 (3)

15 Days (14 Nights) Marigot to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departures: Jan 2027 to Mar 2027
Visit: Saint Martin, Anguilla, Virgin Islands, Saint Kitts and Nevis (+5 more), Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Saint Lucia, Barbados
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$6,740
Balcony
-
Suite
$9,941
From
US$6,740
Save 12,639
Per Person
View Trip
11 Day Southern Caribbean & St. Barts with Seabourn
Cruise
 (1)

11 Days (10 Nights) Miami to Miami
Cruise Line: Seabourn
Ship: Seabourn Quest
Departures: Nov 2027 to Dec 2027
Visit: USA, Puerto Rico, Saint Kitts and Nevis, Montserrat, Saint Barthelemy, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
$4,429
Balcony
$5,311
Suite
$7,957
From
US$4,429
Save 70
Per Person
View Trip
10 Day Sunlit Caribbean Gems with Oceania Cruises
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 12 December 2026
Visit: USA, Virgin Islands, Saint Martin, Saint Barthelemy
Upgrade Your Experience
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,273
Suite
$5,261
From
US$3,273
Save 3,425
Per Person
View Trip
8 Day Eastern Caribbean Cruise: St. Lucia, Dominica & St. Kitts with Azamara Cruises
Cruise
 (3)

8 Days (7 Nights) Bridgetown to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 28 November 2026
Visit: Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin, Saint Barthelemy, Puerto Rico
Azamara Always Included
Inside
$1,629
Oceanview
$2,079
Balcony
$2,643
Suite
$4,156
From
US$1,629
Per Person
View Trip
15 Day An Extended Journey Through Golden Shores & Island Grace with Explora Journeys
Cruise

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 November 2026
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy (+4 more), Turks and Caicos Islands, USA, Antigua and Barbuda, Guadeloupe
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$6,825
Suite
$7,525
From
US$6,825
Per Person
View Trip
13 Day Bridgetown to Miami, Fl with Silversea
Cruise

13 Days (12 Nights) Bridgetown to Miami
Cruise Line: Silversea
Ship: Silver Ray
Departure: 20 March 2028
Visit: Barbados, Saint Vincent, Saint Lucia, Martinique (+7 more), Dominica, Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Puerto Rico, USA
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,280
Suite
$3,630
From
US$3,630
Save 6,570
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
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,700
Suite
$6,450
From
US$5,700
Per Person
View Trip
11 Day Splendid Sunsets with Oceania Cruises
Cruise
 (3)

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 17 February 2028
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Saint Martin
Black Friday Sale + Your World Included
Your World Inclusions
Exclusive Savings
Inside
$3,032
Oceanview
$3,808
Balcony
$4,487
Suite
$6,524
From
US$3,032
Save 3,166
Per Person
View Trip
11 Day Shimmering Reefs, Mighty Ruins with Regent Seven Seas
Cruise

11 Days (10 Nights) Tampa to Tampa
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 11 December 2026
Visit: USA, Cayman Islands, Jamaica, Honduras, Belize, Mexico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,732
Suite
$7,859
From
US$6,732
Save 12,166
Per Person
View Trip
8 Day San Juan to San Juan with Silversea
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 26 February 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Montserrat
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,840
Balcony
$4,480
Suite
$7,640
From
US$3,840
Save 960
Per Person
View Trip
11 Day Southern Caribbean & St. Barts Holiday with Seabourn
Cruise
 (1)

11 Days (10 Nights) Miami to Miami
Cruise Line: Seabourn
Ship: Seabourn Quest
Departure: 18 December 2027
Visit: USA, Puerto Rico, Anguilla, Montserrat, Saint Kitts and Nevis, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
$4,429
Balcony
$5,311
Suite
$7,957
From
US$4,429
Save 70
Per Person
View Trip
8 Day Tropical Retreats with Oceania Cruises
Cruise
 (3)

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 25 January 2027
Visit: USA, Mexico, Belize, Honduras
Black Friday Sale + Your World Included
Your World Inclusions
Exclusive Savings
Inside
$1,999
Oceanview
$2,545
Balcony
$3,078
Suite
$4,388
From
US$1,999
Save 1,999
Per Person
View Trip
8 Day San Juan to San Juan with Silversea
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 21 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia, Antigua and Barbuda
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,680
Balcony
$4,240
Suite
$8,560
From
US$3,680
Save 920
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: 21 December 2026
Visit: USA, Mexico, Honduras, Belize
Your World Inclusions
Upgrade Your Experience
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,031
Suite
$4,486
From
US$3,031
Save 3,167
Per Person
View Trip
9 Day Southern Caribbean Cruise: Martinique, Grenada & U.S. Virgin Islands with Azamara Cruises
Cruise
 (4)

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
$2,724
Balcony
$3,306
Suite
$5,013
From
US$2,229
Per Person
View Trip
10 Day A Journey Through Sacred Cenotes & Hidden Mayan Pyramids with Explora Journeys
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 06 January 2028
Visit: USA, Mexico, Guatemala, Belize, Bahamas
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,355
Suite
$6,230
From
US$5,355
Per Person
View Trip
12 Day Azure Antilles with Oceania Cruises
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 26 February 2026
Visit: USA, Puerto Rico, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, Virgin Islands
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,992
Suite
-
From
US$5,992
Save 6,306
Per Person
View Trip
13 Day Miami to Miami with Silversea
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 18 November 2026
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Montserrat, Saint Kitts and Nevis
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,800
Balcony
$5,760
Suite
$11,480
From
US$4,800
Save 1,200
Per Person
View Trip
9 Day San Juan to Miami, Fl with Silversea
Cruise

9 Days (8 Nights) San Juan to Miami
Cruise Line: Silversea
Ship: Silver Ray
Departure: 26 December 2027
Visit: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique, Saint Kitts and Nevis, USA
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,600
Suite
$9,340
From
US$5,600
Save 1,400
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
Departures: Feb 2026 to Mar 2027
Visit: Barbados, Saint Lucia, Montserrat, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands, Saint Martin
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,012
Suite
$7,510
From
US$4,012
Save 91
Per Person
View Trip
11 Day Caribbean Mystique with Regent Seven Seas
Cruise

11 Days (10 Nights) San Juan to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 30 March 2027
Visit: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+5 more), Saint Barthelemy, Saint Martin, Dominican Republic, Bahamas, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,976
Suite
$7,368
From
US$6,976
Save 13,222
Per Person
View Trip
8 Day Caribbean Gems with Seabourn
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 12 December 2026
Visit: Barbados, Saint Kitts and Nevis, Guadeloupe, Martinique, Dominica, Saint Lucia
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,761
Suite
$7,093
From
US$3,761
Save 63
Per Person
View Trip
8 Day A Journey Of Colourful Treasures & Idyllic Island Scenery with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 06 December 2026
Visit: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Barthelemy, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,850
Suite
$4,445
From
US$3,850
Per Person
View Trip
12 Day Miami to Miami with Silversea
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Ray
Departure: 05 January 2027
Visit: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe, Antigua and Barbuda
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,390
Suite
$9,990
From
US$5,390
Save 2,310
Per Person
View Trip
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