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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 355 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 512 departures starting between September 2024 and April 2027.
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355 Cruises (512 Cruise Departures)
15 Day Yachtsman's Island Jewels with Seabourn
Cruise

15 Days (14 Nights) Bridgetown to Philipsburg
Cruise Line: Seabourn
Ship: Ovation
Departure: 07 February 2026
Countries Visited: Barbados, Saint Kitts and Nevis, Martinique, Guadeloupe (+6 more), Dominica, Saint Lucia, Montserrat, Antigua and Barbuda, Virgin Islands, Sint Maarten
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$9,943
SUITE
$15,665
From 9,943
View Trip
9 Day Bridgetown to Cartagena with Silversea
Cruise

9 Days (8 Nights) Bridgetown to Cartagena
Cruise Line: Silversea
Ship: Silver Moon
Departure: 21 December 2024
Countries Visited: Barbados, Trinidad and Tobago, Saint Lucia, Saint Vincent (+3 more), Aruba, Curacao, Colombia
Port-to-PortExclusive Solo Offer
INSIDE
-
OCEANVIEW
$7,474
BALCONY
$8,662
SUITE
-
Save 826
From 7,474
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
21 Day Holiday Caribbean Enchantment with Seabourn
Cruise

21 Days (20 Nights) San Juan to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 14 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe (+9 more), Martinique, Saint Vincent, Grenada, Barbados, Saint Lucia, Montserrat, Curacao, Aruba, Bonaire
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$12,557
SUITE
$24,254
From 12,557
View Trip
7 Day Splendours of the Caribbean with Emerald Cruises
New ReleaseCruise

7 Days (6 Nights) Saint Thomas to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 03 January 2027
Countries Visited: Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy (+1 more), Puerto Rico
Exclusive Deal
INSIDE
-
OCEANVIEW
$4,599
BALCONY
-
SUITE
$5,777
Save 3,546
From 4,599
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
22 Day Yachtsman's Caribbean Sea Jewels with Seabourn
Cruise

22 Days (21 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 25 January 2025
Countries Visited: Sint Maarten, Virgin Islands, Saint Kitts and Nevis, Martinique (+9 more), Saint Vincent, Grenada, Barbados, Curacao, Bonaire, Aruba, Colombia, Dominican Republic, Antigua and Barbuda
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$17,438
SUITE
-
From 17,438
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
22 Day Island Rhythm & Coastal Charm with Regent Seven Seas
Cruise

22 Days (21 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 20 December 2025
Countries Visited: USA, Aruba, Bonaire, Curacao (+8 more), Grenada, Saint Lucia, Guadeloupe, Saint Kitts and Nevis, Virgin Islands, Mexico, Honduras, Belize
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$17,322
SUITE
$20,570
Save 10,548
From 17,322
View Trip
8 Day Bridgetown to Philipsburg with Silversea
Cruise

8 Days (7 Nights) Bridgetown to Philipsburg
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 12 February 2026
Countries Visited: Barbados, Martinique, Saint Vincent, Dominica (+4 more), Saint Barthelemy, Virgin Islands, Antigua and Barbuda, Saint Martin
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$7,672
BALCONY
$8,464
SUITE
$11,830
Save 828
From 7,672
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
11 Day A Caribbean Holiday with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 18 December 2024
Countries Visited: USA, Dominican Republic, Puerto Rico, Saint Barthelemy (+3 more), Dominica, Antigua and Barbuda, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,060
SUITE
$11,099
Save 3,890
From 10,060
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
$13,315
BALCONY
$14,602
SUITE
$21,631
Save 885
From 13,315
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 Shadow
Departure: 03 December 2024
Countries Visited: USA, Puerto Rico, Montserrat, Saint Lucia (+3 more), Guadeloupe, Saint Barthelemy, Virgin Islands
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$11,434
BALCONY
$12,424
SUITE
$29,353
Save 866
From 11,434
View Trip
15 Day Yachtsman's Island Jewels with Seabourn
Cruise

15 Days (14 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 31 January 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
22 Day Discover the Hidden Treasures of the Caribbean with Emerald Cruises
New ReleaseCruise

22 Days (21 Nights) Marigot to Bridgetown
Cruise Line: Emerald Cruises
Ships: Emerald Sakara
Departures: Feb 2025 to Jan 2026
Countries Visited: Saint Martin, Anguilla, Virgin Islands, Bonaire (+7 more), Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Guadeloupe, Saint Lucia, Barbados, Saint Vincent
Exclusive Deal
INSIDE
-
OCEANVIEW
$14,786
BALCONY
-
SUITE
$17,320
Save 15,192
From 14,786
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
11 Day Heavenly Sunsets with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 03 February 2025
Countries Visited: USA, Mexico, Belize, Guatemala (+3 more), Honduras, Jamaica, Cayman Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,507
SUITE
$11,249
Save 4,043
From 10,507
View Trip
15 Day An Extended Journey Of Caribbean Indulgence And Island Adventures with Explora Journeys
Cruise

15 Days (14 Nights) Bridgetown to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 28 February 2025
Countries Visited: Barbados, Saint Lucia, Martinique, Saint Vincent (+8 more), Trinidad and Tobago, Grenada, Puerto Rico, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands, USA
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$10,593
SUITE
$12,276
From 10,593
View Trip
22 Day An Extended Journey To Southern Serenity And Caribbean Dreaming with Explora Journeys
Cruise

22 Days (21 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 14 January 2025
Countries Visited: USA, Mexico, Bahamas, Saint Barthelemy (+5 more), Guadeloupe, Saint Vincent, Saint Lucia, Antigua and Barbuda, Virgin Islands
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$16,929
SUITE
$19,651
From 16,929
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 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
9 Day Yachtsman's Caribbean with Seabourn
Cruise

9 Days (8 Nights) San Juan to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 14 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe (+4 more), Martinique, Saint Vincent, Grenada, Barbados
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$5,056
SUITE
$9,853
From 5,056
View Trip
8 Day Caribbean Gems with Seabourn
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 14 March 2026
Countries Visited: Barbados, Saint Kitts and Nevis, Guadeloupe, Martinique (+2 more), Dominica, Saint Lucia
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$5,560
SUITE
$8,673
From 5,560
View Trip
8 Day Belize and Honduras: Unexpected Encounters and Nature with Ponant
Cruise

8 Days (7 Nights) Belize City to Belize City
Cruise Line: Ponant
Ship: Le Bellot
Departures: Dec 2024 to Dec 2024
Countries Visited: Belize, Honduras
Exclusive Savings
INSIDE
$9,119
OCEANVIEW
$7,580
BALCONY
$8,793
SUITE
-
Save 153
From 7,580
View Trip
10 Day Bridgetown to Cartagena with Silversea
Cruise

10 Days (9 Nights) Bridgetown to Cartagena
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 22 November 2025
Countries Visited: Barbados, Saint Lucia, Saint Vincent, Bonaire (+3 more), Curacao, Aruba, Colombia
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$8,266
BALCONY
$8,761
SUITE
$14,107
Save 834
From 8,266
View Trip
22 Day Antillean Treasures & Caribbean Sea with Seabourn
Cruise

22 Days (21 Nights) Bridgetown to Philipsburg
Cruise Line: Seabourn
Ship: Ovation
Departure: 21 December 2024
Countries Visited: Barbados, Saint Lucia, Guadeloupe, Anguilla (+10 more), Saint Kitts and Nevis, Virgin Islands, Puerto Rico, Curacao, Bonaire, Aruba, Trinidad and Tobago, Saint Vincent, Antigua and Barbuda, Sint Maarten
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$17,606
SUITE
$31,828
From 17,606
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
8 Day Classic Caribbean Yacht Harbors with Seabourn
Cruise

8 Days (7 Nights) Bridgetown to Philipsburg
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2026 to Feb 2026
Countries Visited: Barbados, Saint Lucia, Montserrat, Antigua and Barbuda (+3 more), Saint Kitts and Nevis, Virgin Islands, Sint Maarten
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$5,476
SUITE
$8,674
From 5,476
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
$12,726
SUITE
$23,160
From 12,726
View Trip
Results: 61-90 of 355

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