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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 362 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 519 departures starting between May 2024 and April 2027.
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362 Cruises (519 Cruise Departures)
8 Day A Journey From Miami To Miami with Explora Journeys
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departures: Dec 2024 to Jan 2025
Countries Visited: USA, Jamaica, Cayman Islands, Mexico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$4,792
SUITE
$5,584
From 4,792
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 Sand, Surf & Rum with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 24 January 2025
Countries Visited: USA, Dominican Republic, Puerto Rico, Saint Barthelemy (+3 more), Dominica, Antigua and Barbuda, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,356
SUITE
$11,396
Save 3,594
From 10,356
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15 Day Festive Caribbean with Oceania Cruises
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 22 December 2024
Countries Visited: USA, Jamaica, Aruba, Curacao (+6 more), Saint Vincent, Barbados, Saint Lucia, Saint Kitts and Nevis, Puerto Rico, Dominican Republic
Exclusive Deal
INSIDE
$6,611
OCEANVIEW
$7,225
BALCONY
$9,670
SUITE
$13,462
Save 2,049
From 6,611
View Trip
11 Day Hidden Caribbean Coves with Oceania Cruises
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 17 December 2024
Countries Visited: USA, Dominican Republic, Puerto Rico, Saint Barthelemy (+3 more), Guadeloupe, Saint Lucia, Antigua and Barbuda
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,467
SUITE
$10,833
Save 2,053
From 6,467
View Trip
11 Day Turquoise Shores, Hidden Isles with Regent Seven Seas
Cruise

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 03 January 2025
Countries Visited: Puerto Rico, Grenada, Saint Vincent, Dominica (+5 more), Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Martinique, Saint Kitts and Nevis
Exclusive DealExclusive Solo Offer
INSIDE
-
OCEANVIEW
$7,554
BALCONY
$10,059
SUITE
$11,544
Save 4,316
From 7,554
View Trip
12 Day Lesser Antilles Isles with Seabourn
Cruise

12 Days (11 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 10 December 2024
Countries Visited: Barbados, Saint Lucia, Antigua and Barbuda, Saint Martin (+5 more), Saint Kitts and Nevis, Virgin Islands, Guadeloupe, Martinique, Grenada
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$6,994
SUITE
$13,390
From 6,994
View Trip
11 Day Hidden Caribbean Coves with Oceania Cruises
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 27 November 2024
Countries Visited: USA, Antigua and Barbuda, Saint Lucia, Guadeloupe (+3 more), Saint Barthelemy, Puerto Rico, Dominican Republic
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$5,398
SUITE
-
Save 2,042
From 5,398
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
22 Day Lesser Antilles In Depth with Seabourn
Cruise

22 Days (21 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 30 November 2024
Countries Visited: Barbados, Saint Vincent, Dominica, Saint Kitts and Nevis (+11 more), Aruba, Bonaire, Curacao, Trinidad and Tobago, Saint Lucia, Antigua and Barbuda, Saint Martin, Virgin Islands, Guadeloupe, Martinique, Grenada
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$13,147
SUITE
$23,160
From 13,147
View Trip
9 Day Fort Lauderdale to Bridgetown with Silversea
Cruise

9 Days (8 Nights) Fort Lauderdale to Bridgetown
Cruise Line: Silversea
Ship: Silver Moon
Departure: 05 March 2025
Countries Visited: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis (+2 more), Martinique, Barbados
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$4,851
BALCONY
$6,633
SUITE
$11,484
From 4,851
View Trip
13 Day Merriment & Joy In The Tropics with Regent Seven Seas
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 22 December 2025
Countries Visited: USA, Saint Kitts and Nevis, Antigua and Barbuda, Martinique (+4 more), Barbados, Grenada, Saint Lucia, Sint Maarten
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$9,765
SUITE
$11,399
Save 6,135
From 9,765
View Trip
15 Day An Extended Journey Of Colourful Caribbean Escapes with Explora Journeys
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 06 December 2024
Countries Visited: USA, Virgin Islands, Dominica, Martinique (+4 more), Barbados, Saint Vincent, Saint Lucia, Saint Kitts and Nevis
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$12,276
SUITE
$14,256
From 12,276
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
12 Day A Journey from Miami to Miami with Explora Journeys
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 24 January 2025
Countries Visited: USA, Saint Barthelemy, Guadeloupe, Saint Vincent (+3 more), Saint Lucia, Antigua and Barbuda, Virgin Islands
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$9,172
SUITE
$11,192
From 9,172
View Trip
9 Day Fort Lauderdale to Cartagena with Silversea
Cruise

9 Days (8 Nights) Fort Lauderdale to Cartagena
Cruise Line: Silversea
Ship: Silver Ray
Departure: 19 December 2024
Countries Visited: Aruba, Colombia, Netherlands Antilles, USA
Port-to-PortExclusive Solo Offer
INSIDE
-
OCEANVIEW
-
BALCONY
-
SUITE
$8,365
From 8,365
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: 04 February 2025
Countries Visited: USA, Cayman Islands, Mexico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$7,351
SUITE
$8,984
From 7,351
View Trip
11 Day Glamorous Gustavia with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 13 December 2024
Countries Visited: USA, Dominican Republic, Puerto Rico, Saint Barthelemy (+3 more), Dominica, Antigua and Barbuda, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$9,327
SUITE
$9,911
Save 4,033
From 9,327
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 II
Departure: 05 January 2025
Countries Visited: USA, Virgin Islands, Guadeloupe, Saint Martin (+1 more), Puerto Rico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$7,237
SUITE
$8,370
From 7,237
View Trip
13 Day Beauty In Bonaire with Regent Seven Seas
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 24 November 2024
Countries Visited: USA, Aruba, Curacao, Bonaire (+4 more), Grenada, Saint Lucia, Saint Barthelemy, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,873
SUITE
$11,913
Save 3,447
From 10,873
View Trip
8 Day Secret Shores & Cultural Gems with Regent Seven Seas
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 21 February 2026
Countries Visited: USA, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,405
SUITE
$9,029
Save 5,515
From 7,405
View Trip
20 Day Caribbean Tour De Force with Oceania Cruises
Cruise

20 Days (19 Nights) Miami to Bridgetown
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 08 January 2026
Countries Visited: USA, Mexico, Belize, Honduras (+9 more), Aruba, Curacao, Trinidad and Tobago, Grenada, Saint Lucia, Saint Vincent, Dominica, Martinique, Barbados
Exclusive Deal
INSIDE
$8,808
OCEANVIEW
$9,719
BALCONY
$12,778
SUITE
$16,461
Save 2,062
From 8,808
View Trip
15 Day A Journey From Miami To Lisbon with Explora Journeys
Cruise

15 Days (14 Nights) Miami to Lisbon
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 14 March 2025
Countries Visited: USA, Puerto Rico, Antigua and Barbuda, Portugal
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$8,573
SUITE
$10,469
From 8,573
View Trip
12 Day Rhythm Of Paradise with Regent Seven Seas
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 11 December 2025
Countries Visited: USA, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+3 more), Martinique, Antigua and Barbuda, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$8,883
SUITE
$10,358
Save 6,277
From 8,883
View Trip
15 Day Yachtsman's Island Jewels with Seabourn
Cruise

15 Days (14 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 07 March 2026
Countries Visited: Sint Maarten, Virgin Islands, Saint Kitts and Nevis, Martinique (+6 more), Saint Vincent, Grenada, Barbados, Guadeloupe, Dominica, Saint Lucia
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$9,942
SUITE
$15,665
From 9,942
View Trip
8 Day A Journey from Miami to San Juan with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 21 February 2025
Countries Visited: USA, Virgin Islands, Guadeloupe, Saint Martin (+1 more), Puerto Rico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$5,029
SUITE
$6,138
From 5,029
View Trip
15 Day Fort Lauderdale to Fort Lauderdale with Silversea
Cruise

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 22 December 2025
Countries Visited: USA, Turks and Caicos Islands, Virgin Islands, Saint Kitts and Nevis (+5 more), Dominica, Martinique, Saint Vincent, Antigua and Barbuda, Puerto Rico
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$14,058
BALCONY
$15,345
SUITE
$21,582
From 14,058
View Trip
11 Day Autumn Atlantic Migration with Seabourn
Cruise

11 Days (10 Nights) St. John's to Bridgetown
Cruise Line: Seabourn
Ship: Venture
Departure: 27 September 2024
Countries Visited: Canada, Puerto Rico, Virgin Islands, Saint Kitts and Nevis (+2 more), Martinique, Barbados
More Moments On Us Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$8,326
SUITE
$10,603
From 8,326
View Trip
11 Day Radiant Roatan with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 23 February 2025
Countries Visited: USA, Mexico, Belize, Guatemala (+3 more), Honduras, Jamaica, Cayman Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$9,913
SUITE
$11,022
Save 4,037
From 9,913
View Trip
13 Day Sunkissed Caribbean Shores with Oceania Cruises
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 07 December 2025
Countries Visited: USA, Aruba, Curacao, Grenada (+2 more), Saint Lucia, Puerto Rico
Exclusive Deal
INSIDE
$3,500
OCEANVIEW
$4,113
BALCONY
$6,103
SUITE
$8,499
Save 2,020
From 3,500
View Trip
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