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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 381 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 539 departures starting between May 2024 and April 2027.
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381 Cruises (539 Cruise Departures)
17 Day Caribbean Holiday Voyage with Azamara Cruises
Cruise

17 Days (16 Nights) Miami to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 22 December 2024
Countries Visited: USA, Bahamas, Virgin Islands, Saint Kitts and Nevis (+5 more), Saint Lucia, Saint Vincent, Barbados, Antigua and Barbuda, Sint Maarten
INSIDE
$5,674
OCEANVIEW
$6,286
BALCONY
$8,585
SUITE
$19,649
From 5,674
View Trip
8 Day Caribbean Gems with Seabourn
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 07 February 2026
Countries Visited: Barbados, Saint Kitts and Nevis, Martinique, Guadeloupe (+2 more), Dominica, Saint Lucia
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$5,560
SUITE
$8,673
From 5,560
View Trip
22 Day Discover the Hidden Treasures of the Caribbean with Emerald Cruises
New ReleaseCruise

22 Days (21 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Nov 2025 to Feb 2026
Countries Visited: Barbados, Saint Vincent, Saint Lucia, Guadeloupe (+6 more), Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Saint Martin, Virgin Islands, Bonaire
Exclusive Deal
INSIDE
-
OCEANVIEW
$13,548
BALCONY
-
SUITE
$17,320
Save 12,149
From 13,548
View Trip
24 Day Elegant Tropical Enclaves with Oceania Cruises
Cruise

24 Days (23 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 08 April 2025
Countries Visited: USA, Antigua and Barbuda, Saint Lucia, Grenada (+5 more), Barbados, Dominica, Saint Barthelemy, Bahamas, Bermuda
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$13,040
SUITE
$20,425
Save 2,100
From 13,040
View Trip
24 Day Collectors Caribbean with Oceania Cruises
Cruise

24 Days (23 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 28 November 2025
Countries Visited: USA, Mexico, Guatemala, Panama (+10 more), Costa Rica, Honduras, Belize, Bahamas, Puerto Rico, Saint Kitts and Nevis, Barbados, Saint Lucia, Antigua and Barbuda, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$12,770
SUITE
$18,175
Save 2,100
From 12,770
View Trip
8 Day A Journey from San Juan to Bridgetown with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 21 February 2025
Countries Visited: Puerto Rico, Aruba, Curacao, Bonaire (+2 more), Trinidad and Tobago, Barbados
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,534
SUITE
$7,945
From 6,420
View Trip
15 Day Exotic Caribbean In Depth with Seabourn
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2025 to Feb 2025
Countries Visited: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+6 more), Virgin Islands, Saint Kitts and Nevis, Sint Maarten, Martinique, Saint Vincent, Grenada
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$10,532
SUITE
$20,630
From 10,532
View Trip
12 Day Leeward Islands Odyssey with Regent Seven Seas
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 10 February 2026
Countries Visited: USA, Bahamas, Puerto Rico, Virgin Islands (+4 more), Saint Barthelemy, Antigua and Barbuda, Saint Lucia, Sint Maarten
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,506
SUITE
$11,546
Save 6,294
From 10,506
View Trip
9 Day A Journey From Miami To Miami with Explora Journeys
Cruise

9 Days (8 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 07 March 2025
Countries Visited: USA, Mexico, Belize, Cayman Islands
INSIDE
-
OCEANVIEW
-
BALCONY
$6,816
SUITE
$8,321
From 5,024
View Trip
10 Day Tropical Harmony with Oceania Cruises
Cruise

10 Days (9 Nights) Bridgetown to Tampa
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 22 February 2026
Countries Visited: Barbados, Aruba, Jamaica, Mexico (+1 more), USA
Exclusive Deal
INSIDE
$4,189
OCEANVIEW
$4,882
BALCONY
$6,485
SUITE
$8,396
Save 2,031
From 4,189
View Trip
10 Day A Journey From Miami To Miami with Explora Journeys
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 05 February 2025
Countries Visited: USA, Dominican Republic, Puerto Rico, Antigua and Barbuda (+1 more), Virgin Islands
INSIDE
-
OCEANVIEW
-
BALCONY
$7,663
SUITE
$9,355
From 6,049
View Trip
11 Day A Journey From Miami To Miami with Explora Journeys
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 05 January 2026
Countries Visited: USA, Jamaica, Honduras, Belize (+1 more), Mexico
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$8,509
SUITE
$10,390
From 8,950
View Trip
12 Day New Year In The Tropics with Regent Seven Seas
Cruise

12 Days (11 Nights) Miami to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 23 December 2024
Countries Visited: USA, Jamaica, Aruba, Curacao (+4 more), Bonaire, Virgin Islands, Sint Maarten, Puerto Rico
Exclusive Deal
INSIDE
-
OCEANVIEW
$8,436
BALCONY
$11,683
SUITE
$13,168
Save 3,874
From 8,436
View Trip
8 Day Radiant New Year with Oceania Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 27 December 2024
Countries Visited: USA, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$4,734
SUITE
$8,229
Save 2,036
From 4,734
View Trip
13 Day Caribbean Flavors & Cozumel with Regent Seven Seas
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 14 March 2026
Countries Visited: USA, Mexico, Guatemala, Belize (+3 more), Honduras, Jamaica, Cayman Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,956
SUITE
$12,877
Save 6,294
From 10,956
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: 19 February 2026
Countries Visited: USA, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$4,407
SUITE
$7,070
Save 2,033
From 4,407
View Trip
15 Day Antillean Treasure Holiday with Seabourn
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 21 December 2024
Countries Visited: Barbados, Saint Lucia, Guadeloupe, Saint Kitts and Nevis (+7 more), Virgin Islands, Puerto Rico, Curacao, Bonaire, Aruba, Trinidad and Tobago, Saint Vincent
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$13,308
SUITE
$23,995
From 13,308
View Trip
11 Day Eastern Caribbean with Silversea
Cruise

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Silversea
Ship: Silver Moon
Departures: Jan 2025 to Feb 2025
Countries Visited: Antigua and Barbuda, Puerto Rico, Saint Kitts and Nevis, USA (+1 more), Virgin Islands
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$9,801
BALCONY
$10,494
SUITE
$27,225
From 9,801
View Trip
13 Day Mesoamerican Majesty with Oceania Cruises
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 28 January 2026
Countries Visited: USA, Mexico, Honduras, Guatemala (+3 more), Belize, Jamaica, Cayman Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,628
SUITE
$12,172
Save 2,062
From 7,628
View Trip
8 Day Basking In The Breeze with Regent Seven Seas
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 24 November 2025
Countries Visited: USA, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$5,919
SUITE
$6,879
Save 5,501
From 5,919
View Trip
11 Day Barefoot Reverie with Regent Seven Seas
Cruise

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 20 January 2025
Countries Visited: Puerto Rico, Grenada, Saint Vincent, Dominica (+5 more), Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Martinique, Saint Kitts and Nevis
Exclusive Deal
INSIDE
-
OCEANVIEW
$7,554
BALCONY
$9,910
SUITE
$11,682
Save 4,316
From 7,554
View Trip
11 Day A Journey From Miami To Miami with Explora Journeys
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 14 February 2026
Countries Visited: USA, Mexico
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$8,509
SUITE
$10,390
From 9,504
View Trip
13 Day Elegant Caribbean with Oceania Cruises
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 16 January 2026
Countries Visited: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis (+2 more), Guadeloupe, Antigua and Barbuda
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,627
SUITE
$12,172
Save 2,063
From 7,627
View Trip
15 Day Exotic Caribbean In Depth with Seabourn
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2025 to Mar 2025
Countries Visited: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+6 more), Virgin Islands, Saint Kitts and Nevis, Sint Maarten, Martinique, Saint Vincent, Grenada
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$11,963
SUITE
$20,462
From 11,963
View Trip
8 Day Sun-splashed Shores with Regent Seven Seas
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 07 November 2024
Countries Visited: USA, Honduras, Belize, Mexico
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,730
SUITE
$7,324
Save 3,110
From 6,730
View Trip
14 Day Eastern Caribbean Voyage with Azamara Cruises
Cruise

14 Days (13 Nights) Miami to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 20 November 2024
Countries Visited: USA, Virgin Islands, Sint Maarten, Dominica (+4 more), Barbados, Saint Lucia, Guadeloupe, Saint Kitts and Nevis
INSIDE
-
OCEANVIEW
$4,347
BALCONY
$5,280
SUITE
$10,044
From 4,347
View Trip
8 Day Joy Of The Islands with Regent Seven Seas
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 13 January 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Dominica (+3 more), Saint Lucia, Antigua and Barbuda, Saint Barthelemy
Exclusive Solo OfferExclusive Deal
INSIDE
-
OCEANVIEW
$5,334
BALCONY
$7,254
SUITE
$8,581
Save 3,546
From 5,334
View Trip
11 Day Caribbean Illumination with Oceania Cruises
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departures: Feb 2026 to Apr 2026
Countries Visited: USA, Puerto Rico, Saint Kitts and Nevis, Saint Lucia (+2 more), Dominica, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,190
SUITE
$9,942
Save 2,052
From 6,190
View Trip
8 Day Western Caribbean Escape with Oceania Cruises
Cruise

8 Days (7 Nights) Tampa to Tampa
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 18 March 2026
Countries Visited: USA, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
$3,644
OCEANVIEW
$4,020
BALCONY
$5,169
SUITE
$6,604
Save 2,026
From 3,644
View Trip
8 Day A Journey Meandering Amongst Lush Leewards Islands with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 03 March 2026
Countries Visited: Puerto Rico, Saint Martin, Guadeloupe, Saint Kitts and Nevis (+2 more), Virgin Islands, USA
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$5,970
SUITE
$7,286
From 7,039
View Trip
Results: 91-120 of 381

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