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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 363 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 523 departures starting between May 2024 and April 2027.
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363 Cruises (523 Cruise Departures)
26 Day Captivating Antillean Treasures with Seabourn
Cruise

26 Days (25 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 10 December 2024
Countries Visited: Barbados, Saint Lucia, Antigua and Barbuda, Saint Martin (+12 more), Saint Kitts and Nevis, Virgin Islands, Guadeloupe, Anguilla, Martinique, Grenada, Puerto Rico, Curacao, Bonaire, Aruba, Trinidad and Tobago, Saint Vincent
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$18,283
SUITE
$33,683
From 18,283
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
$31,659
From 17,438
View Trip
8 Day History and Culture Visiting Caribbean Jewels with Ponant
Cruise

8 Days (7 Nights) Pointe-A-Pitre to Philipsburg
Cruise Line: Ponant
Ship: Le Ponant
Departures: Jan 2025 to Mar 2025
Countries Visited: Guadeloupe, Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy (+2 more), Anguilla, Saint Martin
Exclusive Savings
INSIDE
-
OCEANVIEW
$11,192
BALCONY
$14,162
SUITE
$15,200
Save 236
From 11,192
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, Anguilla, Guadeloupe (+2 more), Saint Martin, Puerto Rico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$5,029
SUITE
$6,138
From 5,029
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
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
11 Day Island Adventures with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 01 December 2025
Countries Visited: USA, Puerto Rico, Saint Barthelemy, Sint Maarten (+3 more), Virgin Islands, Dominican Republic, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$8,437
SUITE
$9,912
Save 6,123
From 8,437
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
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$6,049
SUITE
$7,385
From 6,049
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
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
$12,468
SUITE
$20,462
From 12,468
View Trip
8 Day Passage To Paradise with Regent Seven Seas
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 13 December 2025
Countries Visited: USA, Belize, Honduras, Mexico
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$5,488
SUITE
$7,557
Save 6,542
From 5,488
View Trip
12 Day Caribbean Warmth with Regent Seven Seas
Cruise

12 Days (11 Nights) San Juan to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 06 February 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Kitts and Nevis (+5 more), Curacao, Bonaire, Aruba, Dominican Republic, USA
Exclusive DealExclusive Solo Offer
INSIDE
-
OCEANVIEW
$8,435
BALCONY
$11,395
SUITE
$13,019
Save 4,325
From 8,435
View Trip
12 Day Eclectic Caribbean with Oceania Cruises
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 10 December 2025
Countries Visited: USA, Bahamas, Puerto Rico, Saint Kitts and Nevis (+4 more), Barbados, Saint Lucia, Antigua and Barbuda, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$5,944
SUITE
$9,478
Save 2,046
From 5,944
View Trip
8 Day A Journey To Rum-soaked Isles And Castaway Bliss with Explora Journeys
Cruise

8 Days (7 Nights) Bridgetown to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 15 November 2024
Countries Visited: Barbados, Martinique, Saint Lucia, Antigua and Barbuda (+2 more), Puerto Rico, USA
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$6,192
SUITE
$7,529
From 6,192
View Trip
14 Day Discover the Vibes of the Caribbean with Emerald Cruises
New ReleaseCruise

14 Days (13 Nights) Miami to Saint Thomas
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 30 November 2026
Countries Visited: USA, Bahamas, Turks and Caicos Islands, Puerto Rico (+4 more), Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
$7,712
BALCONY
-
SUITE
$10,430
Save 9,078
From 7,712
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 Ray
Departure: 23 December 2025
Countries Visited: USA, Puerto Rico, Virgin Islands, Bonaire (+3 more), Curacao, Saint Kitts and Nevis, Turks and Caicos Islands
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
-
BALCONY
-
SUITE
$15,048
From 15,048
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
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 San Juan To Miami with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 29 December 2025
Countries Visited: Puerto Rico, Anguilla, Virgin Islands, Dominican Republic (+1 more), USA
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$7,276
SUITE
$8,875
From 7,276
View Trip
8 Day Philipsburg to Bridgetown with Silversea
Cruise

8 Days (7 Nights) Philipsburg to Bridgetown
Cruise Line: Silversea
Ship: Silver Shadow
Departures: Jan 2026 to Feb 2026
Countries Visited: Saint Martin, Virgin Islands, Saint Barthelemy, Dominica (+4 more), Grenada, Martinique, Saint Vincent, Barbados
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$8,910
BALCONY
$9,504
SUITE
$12,078
From 8,910
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
12 Day Idyllic West Indies with Oceania Cruises
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 09 March 2025
Countries Visited: USA, Antigua and Barbuda, Saint Lucia, Barbados (+3 more), Grenada, Dominica, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,953
SUITE
$10,725
Save 2,057
From 6,953
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, Anguilla, Dominica (+5 more), Martinique, 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
17 Day Cartagena to Philipsburg with Silversea
Cruise

17 Days (16 Nights) Cartagena to Philipsburg
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 19 December 2025
Countries Visited: Colombia, Aruba, Curacao, Bonaire (+7 more), Saint Vincent, Barbados, Grenada, Martinique, Virgin Islands, Antigua and Barbuda, Saint Martin
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$11,484
BALCONY
$13,959
SUITE
$22,374
From 11,484
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
15 Day Discover Eastern Caribbean & Grenadines with Emerald Cruises
Cruise

15 Days (14 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Ships: Emerald Sakara, Emerald Azzurra
Departures: Dec 2024 to Nov 2026
Countries Visited: Barbados, Saint Vincent, Saint Lucia, Guadeloupe (+5 more), Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Anguilla, Saint Martin
Exclusive Deal
INSIDE
-
OCEANVIEW
$8,801
BALCONY
-
SUITE
$11,217
Save 10,113
From 8,801
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
8 Day Bridgetown to Philipsburg with Silversea
Cruise

8 Days (7 Nights) Bridgetown to Philipsburg
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 28 December 2025
Countries Visited: Barbados, Saint Vincent, Grenada, Martinique (+3 more), Virgin Islands, Antigua and Barbuda, Saint Martin
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$9,603
BALCONY
$10,395
SUITE
$12,771
From 9,603
View Trip
15 Day Vibrant Hues Of Blue with Regent Seven Seas
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 21 March 2025
Countries Visited: USA, Mexico, Honduras, Belize
Exclusive Deal
INSIDE
-
OCEANVIEW
$10,955
BALCONY
$13,757
SUITE
$15,242
Save 4,795
From 10,955
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
Results: 61-90 of 363

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