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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 359 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 518 departures starting between September 2024 and April 2027.
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359 Cruises (518 Cruise Departures)
15 Day Gems Of The Caribbean with Seabourn
Cruise

15 Days (14 Nights) Philipsburg to Philipsburg
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2026 to Feb 2026
Countries Visited: Sint Maarten, Virgin Islands, Saint Kitts and Nevis, Martinique (+6 more), Saint Vincent, Grenada, Barbados, Saint Lucia, Montserrat, Antigua and Barbuda
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$9,858
SUITE
$15,665
From 9,858
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
$10,210
SUITE
$11,249
Save 4,040
From 10,210
View Trip
15 Day An Extended Journey Of Caribbean Melodies And ABC Islands with Explora Journeys
Cruise

15 Days (14 Nights) Miami to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 14 February 2025
Countries Visited: USA, Anguilla, Virgin Islands, Dominica (+8 more), Guadeloupe, Saint Martin, Puerto Rico, Aruba, Curacao, Bonaire, Trinidad and Tobago, Barbados
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$9,702
SUITE
$11,880
From 9,702
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
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
Exclusive DealUnique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$6,504
SUITE
$7,529
From 6,504
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 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
$11,290
SUITE
$20,630
From 11,290
View Trip
16 Day Antillean Delights with Oceania Cruises
Cruise

16 Days (15 Nights) Oranjestad to Bridgetown
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 27 November 2024
Countries Visited: Aruba, Curacao, Jamaica, Dominican Republic (+10 more), Puerto Rico, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Guadeloupe, Martinique, Saint Lucia, Grenada, Barbados
Cabin Upgrade Offer
INSIDE
$4,828
OCEANVIEW
$4,828
BALCONY
$5,897
SUITE
$8,332
From 4,828
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
Ships: Emerald Sakara
Departures: Dec 2024 to Jan 2026
Countries Visited: Barbados, Saint Vincent, Saint Lucia, Guadeloupe (+7 more), Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Anguilla, Saint Martin, Virgin Islands, Bonaire
Exclusive Deal
INSIDE
-
OCEANVIEW
$13,548
BALCONY
-
SUITE
$17,320
Save 15,188
From 13,548
View Trip
8 Day Eternal Sunshine with Regent Seven Seas
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 30 January 2025
Countries Visited: Puerto Rico, Virgin Islands, Dominica, Saint Lucia (+2 more), 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
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
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$5,658
SUITE
$6,905
From 5,658
View Trip
11 Day Bridgetown to Fort Lauderdale with Silversea
Cruise

11 Days (10 Nights) Bridgetown to Fort Lauderdale
Cruise Line: Silversea
Ship: Silver Moon
Departure: 07 February 2025
Countries Visited: Barbados, Saint Vincent, Saint Lucia, Antigua and Barbuda (+5 more), Saint Barthelemy, Saint Kitts and Nevis, Virgin Islands, Puerto Rico, USA
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$9,801
BALCONY
$10,890
SUITE
$16,137
From 9,801
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
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
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
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
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
$10,653
SUITE
$11,396
Save 3,597
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
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 History and Culture Visiting Caribbean Jewels with Ponant
Cruise

8 Days (7 Nights) Marigot to Pointe-A-Pitre
Cruise Line: Ponant
Ship: Le Ponant
Departures: Mar 2025 to Apr 2025
Countries Visited: Saint Martin, Anguilla, Saint Barthelemy, Saint Kitts and Nevis (+2 more), Antigua and Barbuda, Guadeloupe
Exclusive Savings
INSIDE
-
OCEANVIEW
$10,526
BALCONY
$14,162
SUITE
$15,200
Save 218
From 10,526
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
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
12 Day Fort Lauderdale to Fort Lauderdale with Silversea
Cruise

12 Days (11 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Silversea
Ship: Silver Ray
Departures: Dec 2025 to Feb 2026
Countries Visited: USA, Turks and Caicos Islands, Virgin Islands, Saint Kitts and Nevis (+2 more), Antigua and Barbuda, Saint Martin
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
-
BALCONY
-
SUITE
$11,484
From 11,484
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
11 Day Classic Canal & Tropics with Oceania Cruises
Cruise

11 Days (10 Nights) Panama City to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 04 April 2026
Countries Visited: Panama, Colombia, Curacao, Aruba (+3 more), Jamaica, Cayman Islands, USA
Exclusive Deal
INSIDE
$5,026
OCEANVIEW
$5,482
BALCONY
$7,927
SUITE
$10,927
Save 2,034
From 5,026
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
Departures: Jan 2026 to Feb 2026
Countries Visited: USA, Virgin Islands, Guadeloupe, Saint Lucia (+1 more), Montserrat
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$7,168
SUITE
$8,752
From 7,168
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
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
$6,233
SUITE
$11,366
From 6,233
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
15 Day Discover the Pearls of the Caribbean with Emerald Cruises
New ReleaseCruise

15 Days (14 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Ships: Emerald Sakara, Emerald Azzurra
Departures: Dec 2024 to Dec 2026
Countries Visited: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+6 more), Saint Kitts and Nevis, Saint Barthelemy, Anguilla, Saint Martin, Bonaire, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
$8,999
BALCONY
-
SUITE
$11,563
Save 10,125
From 8,999
View Trip
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