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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)
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
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
15 Day Colorful Caribbean Shores with Regent Seven Seas
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 05 March 2025
Countries Visited: USA, Aruba, Curacao, Bonaire (+6 more), Grenada, Saint Vincent, Barbados, Dominica, Antigua and Barbuda, Sint Maarten
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$14,132
SUITE
$15,310
Save 4,228
From 14,132
View Trip
13 Day Radiant Island Dawns with Oceania Cruises
Cruise

13 Days (12 Nights) Miami to Bridgetown
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 15 January 2026
Countries Visited: USA, Aruba, Curacao, Trinidad and Tobago (+6 more), Grenada, Saint Lucia, Saint Vincent, Dominica, Martinique, Barbados
Exclusive Deal
INSIDE
$5,826
OCEANVIEW
$6,361
BALCONY
$8,262
SUITE
$10,667
Save 2,044
From 5,826
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 Tropical Retreats with Oceania Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 19 February 2026
Countries Visited: USA, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$4,407
SUITE
$7,070
Save 2,033
From 4,407
View Trip
15 Day Exotic Caribbean Isles with Seabourn
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departures: Jan 2026 to Feb 2026
Countries Visited: Barbados, Saint Lucia, Montserrat, Antigua and Barbuda (+6 more), Saint Kitts and Nevis, Virgin Islands, Sint Maarten, Martinique, Saint Vincent, Grenada
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$9,858
SUITE
$15,665
From 9,858
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
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 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: 20 December 2024
Countries Visited: USA, Virgin Islands, Guadeloupe, Saint Martin (+1 more), Puerto Rico
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$7,217
SUITE
$8,776
From 7,217
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
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, Virgin Islands, Dominican Republic, USA
Unique Escapes
INSIDE
-
OCEANVIEW
-
BALCONY
$7,276
SUITE
$8,875
From 7,276
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
$9,949
From 9,949
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, Virgin Islands, Dominica, Guadeloupe (+7 more), 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 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
11 Day Autumn Atlantic Migration with Seabourn
Cruise

11 Days (10 Nights) St. John's to Bridgetown
Cruise Line: Seabourn
Ship: Venture
Departure: 27 September 2024
Countries Visited: Canada, Puerto Rico, Virgin Islands, Saint Kitts and Nevis (+2 more), Martinique, Barbados
More Moments On Us Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$8,326
SUITE
$10,603
From 8,326
View Trip
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 (+11 more), Saint Kitts and Nevis, Virgin Islands, Guadeloupe, 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
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
13 Day Treasures Of Aruba, Bonaire & Curacao with Seabourn
Cruise

13 Days (12 Nights) San Juan to San Juan
Cruise Line: Seabourn
Ship: Ovation
Departure: 02 December 2025
Countries Visited: Puerto Rico, Aruba, Curacao, Bonaire (+6 more), Martinique, Dominica, Montserrat, Saint Kitts and Nevis, Antigua and Barbuda, Virgin Islands
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$7,585
SUITE
$15,243
From 7,585
View Trip
16 Day Leeward Isles Serenade with Oceania Cruises
Cruise

16 Days (15 Nights) Tampa to Tampa
Cruise Line: Oceania Cruises
Ship: Oceania Insignia
Departure: 03 March 2026
Countries Visited: USA, Puerto Rico, Virgin Islands, Sint Maarten (+3 more), Antigua and Barbuda, Dominica, Saint Kitts and Nevis
Exclusive Deal
INSIDE
$7,580
OCEANVIEW
$8,342
BALCONY
$10,936
SUITE
$14,134
Save 2,060
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
$9,009
BALCONY
$9,504
SUITE
$14,058
From 9,009
View Trip
22 Day Caribbean Sea Harbors with Seabourn
Cruise

22 Days (21 Nights) Bridgetown to Philipsburg
Cruise Line: Seabourn
Ship: Ovation
Departure: 01 February 2025
Countries Visited: Barbados, Curacao, Bonaire, Aruba (+9 more), Colombia, Dominican Republic, Antigua and Barbuda, Martinique, Saint Lucia, Guadeloupe, Virgin Islands, Saint Kitts and Nevis, Sint Maarten
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$17,438
SUITE
$32,837
From 17,438
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: 14 February 2026
Countries Visited: USA, Mexico
Unique EscapesPenthouse Dream Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$7,613
SUITE
$9,296
From 7,613
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
$14,058
BALCONY
$15,345
SUITE
$21,582
From 14,058
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
$7,659
OCEANVIEW
$7,580
BALCONY
$8,793
SUITE
-
Save 153
From 7,580
View Trip
13 Day Elegant Caribbean with Oceania Cruises
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 16 January 2026
Countries Visited: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis (+2 more), Guadeloupe, Antigua and Barbuda
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,627
SUITE
$12,172
Save 2,063
From 7,627
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
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
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
15 Day Discover Eastern Caribbean & Grenadines with Emerald Cruises
Cruise

15 Days (14 Nights) Marigot to Bridgetown
Cruise Line: Emerald Cruises
Ships: Emerald Sakara, Emerald Azzurra
Departures: Mar 2025 to Mar 2027
Countries Visited: Saint Martin, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda (+4 more), Guadeloupe, Saint Lucia, Saint Vincent, Barbados
Exclusive Deal
INSIDE
-
OCEANVIEW
$9,049
BALCONY
-
SUITE
$11,563
Save 10,125
From 9,049
View Trip
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