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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 364 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 524 departures starting between May 2024 and April 2027.
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364 Cruises (524 Cruise Departures)
10 Day Willemstad to Bridgetown with Silversea
Cruise

10 Days (9 Nights) Willemstad to Bridgetown
Cruise Line: Silversea
Ship: Silver Moon
Departure: 12 December 2024
Countries Visited: Antigua and Barbuda, Barbados, Netherlands Antilles, Saint Kitts and Nevis (+4 more), Saint Vincent, Trinidad and Tobago, Virgin Islands, Saint Lucia
Port-to-PortExclusive Solo Offer
INSIDE
-
OCEANVIEW
-
BALCONY
-
SUITE
$13,860
From 13,860
View Trip
11 Day Champagne Colored Sands with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 13 February 2025
Countries Visited: USA, Dominican Republic, Puerto Rico, Saint Barthelemy (+3 more), Dominica, Antigua and Barbuda, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,653
SUITE
$11,247
Save 3,897
From 10,653
View Trip
10 Day Bridgetown to Cartagena with Silversea
Cruise

10 Days (9 Nights) Bridgetown to Cartagena
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 10 December 2025
Countries Visited: Barbados, Saint Lucia, Saint Vincent, Curacao (+3 more), Bonaire, Aruba, Colombia
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$9,009
BALCONY
$9,504
SUITE
$14,058
From 9,009
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
13 Day Island Odyssey: Bahamas to the Grenadines with Scenic
Cruise

13 Days (12 Nights) Nassau to Bridgetown
Cruise Line: Scenic
Ship: Scenic Eclipse I
Departure: 24 October 2024
Countries Visited: Bahamas, Puerto Rico, Virgin Islands, Saint Barthelemy (+5 more), Montserrat, Antigua and Barbuda, Guadeloupe, Saint Vincent, Barbados
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$11,232
SUITE
$29,735
Save 4,613
From 11,232
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
$11,121
SUITE
$20,630
From 11,121
View Trip
15 Day Island Anthology with Oceania Cruises
Cruise

15 Days (14 Nights) New York to Oranjestad
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 08 November 2024
Countries Visited: USA, Bermuda, Saint Barthelemy, Dominica (+7 more), Saint Lucia, Barbados, Saint Vincent, Grenada, Bonaire, Curacao, Aruba
Cabin Upgrade Offer
INSIDE
$4,623
OCEANVIEW
$4,623
BALCONY
$5,761
SUITE
$8,286
From 4,623
View Trip
8 Day Yachtsman's Caribbean with Seabourn
Cruise

8 Days (7 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2025 to Mar 2025
Countries Visited: Sint Maarten, Virgin Islands, Saint Kitts and Nevis, Martinique (+3 more), Saint Vincent, Grenada, Barbados
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$6,149
SUITE
$11,366
From 6,149
View Trip
9 Day Bridgetown to Bridgetown with Silversea
Cruise

9 Days (8 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Moon
Departure: 13 March 2025
Countries Visited: Barbados, Saint Vincent, Aruba, Bonaire (+2 more), Curacao, Saint Lucia
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$5,049
BALCONY
$6,930
SUITE
$11,781
From 5,049
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 II
Departures: Nov 2024 to Feb 2025
Countries Visited: USA, Virgin Islands, Dominica, Guadeloupe (+2 more), Saint Martin, Puerto Rico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$5,158
SUITE
$6,272
From 5,158
View Trip
10 Day A Journey of Infinite Enchantment in the Lesser Antillies with Explora Journeys
Cruise

10 Days (9 Nights) Miami to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 05 December 2025
Countries Visited: USA, Virgin Islands, Guadeloupe, Dominica (+4 more), Saint Lucia, Grenada, Saint Vincent, Barbados
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$6,049
SUITE
$7,385
From 6,049
View Trip
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
15 Day Bridgetown to Bridgetown with Silversea
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 22 December 2025
Countries Visited: Barbados, Saint Lucia, Grenada, Saint Martin (+5 more), Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Dominica, Saint Vincent
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$14,553
BALCONY
$16,533
SUITE
$15,543
From 14,553
View Trip
8 Day Quintessential Caribbean with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) San Juan to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Jan 2027 to Mar 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe (+2 more), Antigua and Barbuda, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
$5,836
BALCONY
-
SUITE
$7,375
Save 3,559
From 5,836
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
$11,682
SUITE
$14,256
From 11,682
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 II
Departure: 22 December 2025
Countries Visited: USA, Dominican Republic, Virgin Islands, Saint Martin (+1 more), Puerto Rico
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$6,816
SUITE
$8,286
From 6,816
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
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: 24 March 2025
Countries Visited: USA, Guatemala, Honduras, Belize (+1 more), Mexico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$6,168
SUITE
$7,519
From 6,168
View Trip
18 Day Enchantment Of The Lesser Antilles with Seabourn
Cruise

18 Days (17 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 23 November 2024
Countries Visited: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+8 more), Saint Kitts and Nevis, Grenada, Saint Vincent, Dominica, Aruba, Curacao, Bonaire, Trinidad and Tobago
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$12,975
SUITE
$19,959
From 12,975
View Trip
8 Day A Journey From Miami To Bridgetown with Explora Journeys
Cruise

8 Days (7 Nights) Miami to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 23 December 2024
Countries Visited: USA, Puerto Rico, Virgin Islands, Dominica (+2 more), Saint Lucia, Barbados
INSIDE
-
OCEANVIEW
-
BALCONY
$7,618
SUITE
$9,261
From 7,618
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
8 Day Tropical Retreats with Oceania Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 08 January 2026
Countries Visited: USA, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
$3,190
OCEANVIEW
$3,645
BALCONY
$4,863
SUITE
$6,309
Save 2,020
From 3,190
View Trip
9 Day Cruising the Caribbean's Windward Islands - with Smithsonian Journeys with Ponant
Cruise

9 Days (8 Nights) Vieux Fort to Vieux Fort
Cruise Line: Ponant
Ship: Le Champlain
Departure: 30 January 2025
Countries Visited: Saint Lucia, Dominica, Guadeloupe, Saint Vincent (+2 more), Grenada, Barbados
Exclusive Savings
INSIDE
$14,682
OCEANVIEW
$7,813
BALCONY
$9,812
SUITE
-
Save 147
From 7,813
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
7 Day A Journey Of Sunshine Caribbean Shores And Sizzling Magnetism with Explora Journeys
Cruise

7 Days (6 Nights) Bridgetown to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 10 December 2024
Countries Visited: Barbados, Guadeloupe, Antigua and Barbuda, Puerto Rico
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$4,316
SUITE
$5,267
From 4,316
View Trip
11 Day Maya & Isle Mementos with Oceania Cruises
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 29 December 2025
Countries Visited: USA, Mexico, Belize, Honduras (+2 more), Jamaica, Cayman Islands
Exclusive Deal
INSIDE
$4,964
OCEANVIEW
$5,499
BALCONY
$7,558
SUITE
$10,548
Save 2,036
From 4,964
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 Bridgetown to Bridgetown with Silversea
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departures: Dec 2025 to Mar 2026
Countries Visited: Barbados, Saint Vincent, Martinique, Saint Barthelemy (+3 more), Dominica, Grenada, Saint Lucia
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$7,722
BALCONY
$8,910
SUITE
$8,118
From 7,722
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
13 Day Fort Lauderdale to Bridgetown with Silversea
Cruise

13 Days (12 Nights) Fort Lauderdale to Bridgetown
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 10 November 2025
Countries Visited: USA, Puerto Rico, Virgin Islands, Saint Barthelemy (+6 more), Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Saint Lucia, Barbados
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$10,494
BALCONY
$11,979
SUITE
$18,909
From 10,494
View Trip
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