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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)
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
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
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
15 Day A Blissful Escape with Regent Seven Seas
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 28 February 2026
Countries Visited: USA, Aruba, Curacao, Bonaire (+5 more), Grenada, Guadeloupe, Martinique, Saint Kitts and Nevis, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$13,608
SUITE
$14,865
Save 7,072
From 13,608
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
8 Day Joy Of The Islands with Regent Seven Seas
Cruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 13 January 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Dominica (+3 more), Saint Lucia, 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
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
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
$6,192
SUITE
$7,529
From 6,192
View Trip
18 Day Yucatan Gems & Serene Isles with Regent Seven Seas
Cruise

18 Days (17 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 24 November 2025
Countries Visited: USA, Mexico, Belize, Honduras (+6 more), Puerto Rico, Saint Barthelemy, Sint Maarten, Virgin Islands, Dominican Republic, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$13,613
SUITE
$15,979
Save 9,467
From 13,613
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
15 Day An Extended Journey of Caribbean Culture and Tropical Trails with Explora Journeys
Cruise

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 21 February 2025
Countries Visited: Puerto Rico, Aruba, Curacao, Bonaire (+6 more), Trinidad and Tobago, Barbados, Saint Lucia, Martinique, Saint Vincent, Grenada
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$10,593
SUITE
$8,365
From 8,365
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
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
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 Yachting Treasures with Oceania Cruises
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 19 December 2025
Countries Visited: USA, Puerto Rico, Saint Kitts and Nevis, Antigua and Barbuda (+2 more), Sint Maarten, Virgin Islands
Exclusive Deal
INSIDE
$4,805
OCEANVIEW
$5,270
BALCONY
$7,250
SUITE
$10,398
Save 2,035
From 4,805
View Trip
11 Day Barefoot Reverie with Regent Seven Seas
Cruise

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 20 January 2025
Countries Visited: Puerto Rico, Grenada, Saint Vincent, Dominica (+5 more), Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Martinique, Saint Kitts and Nevis
Exclusive Deal
INSIDE
-
OCEANVIEW
$7,554
BALCONY
$9,910
SUITE
$11,682
Save 4,316
From 7,554
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
13 Day Antillean Adventure with Oceania Cruises
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 27 March 2025
Countries Visited: USA, Aruba, Curacao, Bonaire (+5 more), Grenada, Saint Lucia, Saint Kitts and Nevis, Puerto Rico, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,609
SUITE
$11,846
Save 2,061
From 7,609
View Trip
27 Day Antilles & Atlantic Gems with Oceania Cruises
Cruise

27 Days (26 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 09 March 2026
Countries Visited: USA, Aruba, Curacao, Grenada (+5 more), Saint Vincent, Martinique, Virgin Islands, Bermuda, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$15,447
SUITE
$24,693
Save 2,123
From 15,447
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: 05 January 2026
Countries Visited: USA, Jamaica, Honduras, Belize (+1 more), Mexico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$7,168
SUITE
$8,752
From 7,168
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
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
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
24 Day Elegant Tropical Enclaves with Oceania Cruises
Cruise

24 Days (23 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 08 April 2025
Countries Visited: USA, Antigua and Barbuda, Saint Lucia, Grenada (+5 more), Barbados, Dominica, Saint Barthelemy, Bahamas, Bermuda
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$14,713
SUITE
$21,188
Save 2,117
From 14,713
View Trip
8 Day Lush Islands, Lovely Shores with Regent Seven Seas
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 03 January 2026
Countries Visited: USA, Mexico, Honduras, Belize
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$5,634
SUITE
$7,693
Save 5,496
From 5,634
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
$12,554
SUITE
-
From 12,554
View Trip
14 Day Fort Lauderdale to Lima with Silversea
Cruise

14 Days (13 Nights) Fort Lauderdale to Lima
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 06 January 2026
Countries Visited: USA, Mexico, Costa Rica, Panama (+2 more), Ecuador, Peru
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$15,493
BALCONY
$16,780
SUITE
-
From 15,493
View Trip
17 Day Iconic Islands To Empire City with Regent Seven Seas
Cruise

17 Days (16 Nights) Miami to New York
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 24 June 2025
Countries Visited: USA, Aruba, Curacao, Bonaire (+5 more), Grenada, Saint Lucia, Saint Barthelemy, Puerto Rico, Bermuda
Exclusive Solo OfferExclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$14,206
SUITE
$15,978
Save 7,224
From 14,206
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, Anguilla, Dominica, Guadeloupe (+2 more), Saint Martin, Puerto Rico
Mutiple Deals Available
INSIDE
-
OCEANVIEW
-
BALCONY
$5,158
SUITE
$6,272
From 5,158
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
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