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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 539 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 702 departures starting between January 2026 and April 2028.
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539 Cruises (702 Cruise Departures)
15 Day Caribbean Celebration with Regent Seven Seas
Cruise

15 Days (14 Nights) Tampa to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 21 December 2026
Visit: USA, Cayman Islands, Jamaica, Aruba (+5 more), Curacao, Bonaire, Saint Kitts and Nevis, Saint Martin, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,038
Suite
$10,410
From
US$9,038
Save 15,760
Per Person
View Trip
15 Day Caribbean Compass with Regent Seven Seas
Cruise

15 Days (14 Nights) Miami to New York
Cruise Line: Regent Seven Seas
Ship: Seven Seas Mariner
Departure: 15 April 2027
Visit: USA, Aruba, Curacao, Bonaire (+4 more), Saint Kitts and Nevis, Saint Barthelemy, Antigua and Barbuda, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,139
Suite
$10,315
From
US$9,139
Save 16,459
Per Person
View Trip
11 Day Caribbean Island Hopping: Sint Maarten to Barbados with Emerald Cruises
New ReleaseCruise

11 Days (10 Nights) Philipsburg to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 12 January 2028
Visit: Saint Martin, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+5 more), Antigua and Barbuda, Guadeloupe, Saint Lucia, Saint Vincent, Barbados
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$6,817
Balcony
-
Suite
$9,242
From
US$6,817
Save 9,173
Per Person
View Trip
15 Day An Extended Journey from Ocean Calm to Vibrant Culture with Explora Journeys
Cruise

15 Days (14 Nights) San Juan to Bridgetown
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 07 March 2027
Visit: Puerto Rico, Saint Martin, Saint Barthelemy, Saint Kitts and Nevis (+6 more), Turks and Caicos Islands, USA, Antigua and Barbuda, Dominica, Saint Vincent, Barbados
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$7,760
Suite
$8,920
From
US$7,760
Per Person
View Trip
8 Day Wonders of the Caribbean with Ponant
Cruise
 (1)

8 Days (7 Nights) Fort-de-France to Fort-de-France
Cruise Line: Ponant
Ship: Le Bougainville
Departures: Dec 2026 to Jan 2027
Visit: Martinique, Antigua and Barbuda, Virgin Islands, Saint Barthelemy, Guadeloupe
Inside
-
Oceanview
-
Balcony
$5,060
Suite
$7,560
From
US$5,060
Per Person
View Trip
12 Day San Juan to San Juan with Silversea
Cruise

12 Days (11 Nights) San Juan to San Juan
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 25 January 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Dominica (+4 more), Saint Vincent, Grenada, Curacao, Bonaire
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,800
Balcony
$5,520
Suite
$11,240
From
US$4,800
Save 1,200
Per Person
View Trip
18 Day An Extended Journey Into Tropical Utopia, Coral Wonders & Blissful Beaches with Explora Journeys
Cruise

18 Days (17 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 20 February 2026
Visit: Puerto Rico, Aruba, Curacao, Bonaire (+7 more), Barbados, Guadeloupe, Saint Martin, Virgin Islands, Antigua and Barbuda, Anguilla, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$7,595
Suite
$8,155
From
US$7,595
Per Person
View Trip
13 Day Bon Bini Aruba with Regent Seven Seas
Cruise

13 Days (12 Nights) Panama City to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 14 March 2028
Visit: Panama, Colombia, Aruba, Curacao (+4 more), Grenada, Dominica, Virgin Islands, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,458
Suite
$8,850
From
US$8,458
Save 14,740
Per Person
View Trip
8 Day A Journey Through Island Charm & Cultural Treasures with Explora Journeys
Cruise

8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora IV
Departures: Mar 2028 to Apr 2028
Visit: USA, Turks and Caicos Islands, Saint Barthelemy, Antigua and Barbuda, Anguilla, Puerto Rico
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,520
From
US$3,915
Per Person
View Trip
8 Day Sea, Sun & Salsa with Regent Seven Seas
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 20 November 2027
Visit: USA, Belize, Guatemala, Mexico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,063
Suite
$5,259
From
US$5,063
Save 10,235
Per Person
View Trip
15 Day An Extended Journey of Tropical Harmony & Natural Wonders with Explora Journeys
Cruise

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 15 November 2026
Visit: Puerto Rico, Anguilla, Antigua and Barbuda, Virgin Islands (+4 more), Dominican Republic, USA, Guadeloupe, Saint Martin
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$6,600
Suite
$7,575
From
US$6,600
Per Person
View Trip
8 Day A Journey From Exciting Escapades To Idyllic Tranquillity with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 01 March 2027
Visit: Puerto Rico, Antigua and Barbuda, Anguilla, Virgin Islands, Turks and Caicos Islands, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$4,125
Suite
$4,650
From
US$4,125
Per Person
View Trip
22 Day Caribbean Celebration with Cunard
Cruise
 (13)

22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 08 December 2026
Visit: USA, Cayman Islands, Jamaica, Honduras (+6 more), Mexico, Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados, Saint Martin
Inside
$2,297
Oceanview
$2,449
Balcony
$3,124
Suite
$7,936
From
US$2,297
Per Person
View Trip
17 Day Discover the Best of the Caribbean with Emerald Cruises
New ReleaseCruise
 (3)

17 Days (16 Nights) Marigot to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 20 November 2026
Visit: Saint Martin, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda (+5 more), Guadeloupe, Martinique, Saint Lucia, Saint Vincent, Barbados
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$10,653
From
US$10,653
Save 13,427
Per Person
View Trip
8 Day Tropical Retreats with Oceania Cruises
Cruise
 (3)

8 Days (7 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 25 January 2027
Visit: USA, Mexico, Belize, Honduras
Black Friday Sale + Your World Included
Your World Inclusions
Exclusive Savings
Inside
$1,999
Oceanview
$2,545
Balcony
$3,078
Suite
$4,388
From
US$1,999
Save 1,999
Per Person
View Trip
14 Day Caribbean Celebration with Cunard
Cruise
 (6)

14 Days (13 Nights) New York to New York
Cruise Line: Cunard
Ship: Queen Mary 2
Departure: 21 December 2027
Visit: USA, Saint Kitts and Nevis, Saint Lucia, Barbados, Dominica, Saint Martin
Inside
$2,489
Oceanview
$3,429
Balcony
$3,539
Suite
$8,816
From
US$2,489
Per Person
View Trip
8 Day Pearls of the Caribbean with Ponant
Cruise
 (1)

8 Days (7 Nights) Fort-de-France to Fort-de-France
Cruise Line: Ponant
Ship: Le Bougainville
Departures: Dec 2026 to Feb 2027
Visit: Martinique, Saint Vincent, Saint Lucia, Guadeloupe
Inside
-
Oceanview
-
Balcony
$5,060
Suite
$7,560
From
US$5,060
Per Person
View Trip
11 Day Maya Culture & Cuisine with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 04 March 2028
Visit: USA, Mexico, Belize, Honduras, Jamaica, Cayman Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,293
Suite
$6,734
From
US$6,293
Save 12,505
Per Person
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 2026 to Mar 2027
Visit: Saint Martin, Anguilla, Saint Barthelemy, Saint Kitts and Nevis (+5 more), Antigua and Barbuda, Guadeloupe, Saint Lucia, Saint Vincent, Barbados
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$6,756
Balcony
-
Suite
$9,957
From
US$6,756
Save 34,102
Per Person
View Trip
10 Day A Journey of Palm - Shaded Elegance & Caribbean Cultural Fusion with Explora Journeys
Cruise

10 Days (9 Nights) Miami to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 04 December 2027
Visit: USA, Dominican Republic, Puerto Rico, Virgin Islands, Saint Barthelemy
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$5,020
Suite
$5,840
From
US$5,020
Per Person
View Trip
11 Day Classic Canal & Tropics with Oceania Cruises
Cruise
 (3)

11 Days (10 Nights) Panama City to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Marina
Departure: 16 January 2028
Visit: Panama, Colombia, Curacao, Aruba, Jamaica, Cayman Islands, USA
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
$3,043
Oceanview
$4,013
Balcony
$4,789
Suite
$6,729
From
US$3,043
Save 3,155
Per Person
View Trip
9 Day Beaches of the Grenadines with Emerald Cruises
New ReleaseCruise
 (3)

9 Days (8 Nights) Bridgetown to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 11 December 2027
Visit: Barbados, Saint Lucia, Saint Vincent
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$5,085
Balcony
-
Suite
$7,025
From
US$5,085
Save 7,405
Per Person
View Trip
15 Day Discover Eastern Caribbean & Grenadines with Emerald Cruises
Cruise

15 Days (14 Nights) Philipsburg to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 12 February 2028
Visit: Saint Martin, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+5 more), Antigua and Barbuda, Guadeloupe, Saint Lucia, Saint Vincent, Barbados
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$11,645
Balcony
-
Suite
$15,040
From
US$11,645
Save 12,335
Per Person
View Trip
11 Day Tropical Island Havens with Oceania Cruises
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departures: Dec 2026 to Mar 2027
Visit: USA, Virgin Islands, Saint Martin, Saint Barthelemy, Saint Kitts and Nevis
Multiple Deals Available
Inside
-
Oceanview
-
Balcony
$3,613
Suite
$6,038
From
US$3,613
Save 4,301
Per Person
View Trip
14 Day Bountiful Caribbean with Oceania Cruises
Cruise

14 Days (13 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Allura
Departure: 07 January 2027
Visit: USA, Cayman Islands, Jamaica, Aruba (+4 more), Curacao, Grenada, Guadeloupe, Virgin Islands
Your World Inclusions
Black Friday Sale + Your World Included
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$5,559
Suite
$7,790
From
US$5,559
Save 5,839
Per Person
View Trip
22 Day Caribbean Celebration with Cunard
Cruise
 (13)

22 Days (21 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 17 December 2026
Visit: USA, Puerto Rico, Antigua and Barbuda, Saint Lucia (+6 more), Barbados, Saint Martin, Cayman Islands, Jamaica, Honduras, Mexico
Inside
$2,367
Oceanview
$2,443
Balcony
$3,175
Suite
$10,704
From
US$2,367
Per Person
View Trip
8 Day Reverie Under Sail in the Heart of the Lesser Antilles with Ponant
Cruise

8 Days (7 Nights) Marigot to Philipsburg
Cruise Line: Ponant
Ship: Le Ponant
Departure: 14 March 2026
Visit: Saint Martin, Anguilla, Virgin Islands
Inside
-
Oceanview
$9,870
Balcony
-
Suite
-
From
US$9,870
Per Person
View Trip
10 Day Western Caribbean with Cunard
Cruise
 (13)

10 Days (9 Nights) Miami to Miami
Cruise Line: Cunard
Ship: Queen Elizabeth
Departure: 03 March 2026
Visit: USA, Turks and Caicos Islands, Jamaica, Belize, Mexico
Inside
$739
Oceanview
$759
Balcony
$999
Suite
$8,319
From
US$739
Per Person
View Trip
8 Day A Journey Through Beguiling Tropical Elegance To Vibrant Island Delights with Explora Journeys
Cruise
 (1)

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 27 February 2028
Visit: Puerto Rico, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Bahamas, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,415
From
US$3,915
Per Person
View Trip
11 Day Bridgetown to Bridgetown with Silversea
Cruise

11 Days (10 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 15 January 2027
Visit: Barbados, Saint Vincent, Grenada, Aruba (+4 more), Curacao, Bonaire, Martinique, Saint Lucia
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,720
Balcony
$5,280
Suite
$4,800
From
US$4,720
Save 1,180
Per Person
View Trip
Results: 1-30 of 539

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