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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)
12 Day Bridgetown to Bridgetown with Silversea
Cruise

12 Days (11 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Moon
Departure: 27 January 2025
Countries Visited: Aruba, Barbados, Grenada, Martinique (+4 more), Netherlands Antilles, Saint Vincent, Trinidad and Tobago, Saint Lucia
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$10,989
BALCONY
$12,375
SUITE
$18,612
From 10,989
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 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
11 Day Cartagena to New York with Silversea
Cruise

11 Days (10 Nights) Cartagena to New York
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 08 June 2024
Countries Visited: Aruba, Colombia, USA, Virgin Islands
Port-to-PortExclusive Solo Offer
INSIDE
-
OCEANVIEW
$5,494
BALCONY
$7,276
SUITE
-
From 5,494
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 Bridgetown to Bridgetown with Silversea
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 19 January 2026
Countries Visited: Barbados, Saint Vincent, Aruba, Bonaire (+1 more), Curacao
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$8,811
BALCONY
$10,494
SUITE
$9,306
From 8,811
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 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
12 Day Idyllic West Indies with Oceania Cruises
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 08 April 2025
Countries Visited: USA, Antigua and Barbuda, Saint Lucia, Grenada (+3 more), Barbados, Dominica, Saint Barthelemy
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$6,972
SUITE
$10,734
Save 2,058
From 6,972
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 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
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,618
SUITE
$9,261
From 11,905
View Trip
13 Day Beauty In Bonaire with Regent Seven Seas
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 24 November 2024
Countries Visited: USA, Aruba, Curacao, Bonaire (+4 more), Grenada, Saint Lucia, Saint Barthelemy, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,873
SUITE
$11,913
Save 3,447
From 10,873
View Trip
16 Day Fort Lauderdale to New York with Silversea
Cruise

16 Days (15 Nights) Fort Lauderdale to New York
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 27 May 2025
Countries Visited: USA, Jamaica, Aruba, Saint Barthelemy (+2 more), Virgin Islands, Bermuda
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$12,672
BALCONY
$13,167
SUITE
$20,493
From 12,672
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
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
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 145
From 7,580
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
8 Day Caribbean Gems with Seabourn
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Ovation
Departure: 14 March 2026
Countries Visited: Barbados, Saint Kitts and Nevis, Guadeloupe, Martinique (+2 more), Dominica, Saint Lucia
The Sail Away Event
INSIDE
-
OCEANVIEW
-
BALCONY
$5,560
SUITE
$8,673
From 5,560
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
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$12,415
SUITE
$15,088
From 12,474
View Trip
12 Day A Journey from Miami to Miami with Explora Journeys
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 24 January 2025
Countries Visited: USA, Saint Barthelemy, Guadeloupe, Saint Vincent (+3 more), Saint Lucia, Antigua and Barbuda, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$10,766
SUITE
$12,509
From 14,429
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
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 II
Departure: 05 January 2025
Countries Visited: USA, Virgin Islands, Guadeloupe, Saint Martin (+1 more), Puerto Rico
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$8,088
SUITE
$9,355
From 9,044
View Trip
15 Day An Extended Journey Of Caribbean Rhythms with Explora Journeys
Cruise

15 Days (14 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 22 November 2024
Countries Visited: USA, Dominica, Guadeloupe, Saint Martin (+5 more), Puerto Rico, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$13,038
SUITE
$15,088
From 15,246
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
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: Feb 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
$11,217
Save 10,125
From 9,049
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
$5,997
BALCONY
$7,254
SUITE
$8,581
Save 3,553
From 5,997
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
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 Fort Lauderdale to Fort Lauderdale with Silversea
Cruise

15 Days (14 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 03 December 2024
Countries Visited: Puerto Rico, Turks and Caicos Islands, USA, Virgin Islands (+1 more), Saint Lucia
Port-to-PortDoor-to-Door Upgrade Option
INSIDE
-
OCEANVIEW
$11,682
BALCONY
$12,672
SUITE
$17,028
From 11,682
View Trip
10 Day A Journey of Infinite Enchantment in the Lesser Antillies with Explora Journeys
Cruise

10 Days (9 Nights) Miami to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 05 December 2025
Countries Visited: USA, Virgin Islands, Guadeloupe, Dominica (+4 more), Saint Lucia, Grenada, Saint Vincent, Barbados
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
$7,663
SUITE
$9,355
From 7,534
View Trip
Results: 121-150 of 381

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