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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 381 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 539 departures starting between May 2024 and April 2027.
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381 Cruises (539 Cruise Departures)
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
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,618
SUITE
$9,261
From 12,608
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
$10,356
SUITE
$11,396
Save 3,594
From 10,356
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 Solo OfferExclusive Deal
INSIDE
-
OCEANVIEW
$9,099
BALCONY
$11,395
SUITE
$13,019
Save 4,331
From 9,099
View Trip
8 Day A Journey to Yacht-filled Harbours and Scenic Sail-ins with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ships: Explora II, Explora I
Departure: 28 February 2025
Countries Visited: Puerto Rico, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis (+2 more), Virgin Islands, USA
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,534
SUITE
$7,945
From 5,742
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 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
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$9,311
SUITE
$11,380
From 11,024
View Trip
8 Day A Journey From Miami To Miami with Explora Journeys
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 28 November 2025
Countries Visited: USA, Mexico
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$5,970
SUITE
$7,286
From 5,861
View Trip
15 Day Jewels Of The Caribbean Sea with Seabourn
Cruise

15 Days (14 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 01 February 2025
Countries Visited: Barbados, Curacao, Bonaire, Aruba (+4 more), Colombia, Dominican Republic, Antigua and Barbuda, Martinique
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$12,465
SUITE
$24,331
From 12,465
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
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
$13,040
SUITE
$20,425
Save 2,100
From 13,040
View Trip
19 Day Iridescent Isles & Inlets with Oceania Cruises
Cruise

19 Days (18 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 09 March 2025
Countries Visited: USA, Antigua and Barbuda, Saint Lucia, Barbados (+6 more), Grenada, Dominica, Saint Barthelemy, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$11,319
SUITE
$16,071
Save 2,091
From 11,319
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
14 Day Eastern Caribbean Voyage with Azamara Cruises
Cruise

14 Days (13 Nights) Miami to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 20 November 2024
Countries Visited: USA, Virgin Islands, Sint Maarten, Dominica (+4 more), Barbados, Saint Lucia, Guadeloupe, Saint Kitts and Nevis
INSIDE
-
OCEANVIEW
$4,347
BALCONY
$5,280
SUITE
$10,044
From 4,347
View Trip
20 Day Caribbean Twilight with Oceania Cruises
Cruise

20 Days (19 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 20 March 2025
Countries Visited: USA, Mexico, Belize, Honduras (+8 more), Aruba, Curacao, Bonaire, Grenada, Saint Lucia, Saint Kitts and Nevis, Puerto Rico, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,748
SUITE
$16,886
Save 2,082
From 10,748
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
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 Tropical Retreats with Oceania Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 20 March 2025
Countries Visited: USA, Mexico, Belize, Honduras
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$4,526
SUITE
$7,040
Save 2,034
From 4,526
View Trip
8 Day Cruising the Leeward Islands with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) Marigot to Marigot
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Sakara
Departures: Nov 2024 to Apr 2027
Countries Visited: Saint Martin, Virgin Islands, Bonaire, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
$5,490
BALCONY
-
SUITE
$6,747
Save 4,074
From 5,490
View Trip
11 Day Fort Lauderdale to Fort Lauderdale with Silversea
Cruise

11 Days (10 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Silversea
Ship: Silver Ray
Departures: Dec 2025 to Mar 2026
Countries Visited: USA, Turks and Caicos Islands, Virgin Islands, Saint Kitts and Nevis (+2 more), Saint Martin, Puerto Rico
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
-
BALCONY
-
SUITE
$10,593
From 10,593
View Trip
10 Day Caribbean Journey Voyage with Azamara Cruises
Cruise

10 Days (9 Nights) Bridgetown to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 22 March 2025
Countries Visited: Barbados, Saint Lucia, Dominica, Antigua and Barbuda (+4 more), Sint Maarten, Virgin Islands, Puerto Rico, USA
Circle Club Voyage
INSIDE
$3,524
OCEANVIEW
$3,749
BALCONY
$4,990
SUITE
-
From 3,524
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
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$19,518
SUITE
$22,691
From 25,393
View Trip
13 Day Tropical Connoisseur with Oceania Cruises
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 05 December 2024
Countries Visited: USA, Mexico, Guatemala, Belize (+4 more), Honduras, Cayman Islands, Jamaica, Bahamas
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,996
SUITE
$9,550
Save 2,054
From 6,996
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
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$8,509
SUITE
$10,390
From 8,950
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
9 Day A Journey From Bridgetown To Miami with Explora Journeys
Cruise

9 Days (8 Nights) Bridgetown to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 30 December 2024
Countries Visited: Barbados, Grenada, Bonaire, Curacao (+2 more), Aruba, USA
INSIDE
-
OCEANVIEW
-
BALCONY
$9,311
SUITE
$11,380
From 8,821
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
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
$5,813
SUITE
$11,366
From 5,813
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
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
$12,975
SUITE
$19,959
From 12,975
View Trip
11 Day Hidden Caribbean Coves with Oceania Cruises
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 27 November 2024
Countries Visited: USA, Antigua and Barbuda, Saint Lucia, Guadeloupe (+3 more), Saint Barthelemy, Puerto Rico, Dominican Republic
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$5,398
SUITE
-
Save 2,042
From 5,398
View Trip
Results: 61-90 of 381

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