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Caribbean Luxury Cruises

Explore the best luxury cruises to the Caribbean. Choose from 537 unique cruise itineraries from 10 leading cruise lines. December is the most popular month to join a luxury cruise to the Caribbean with 700 departures starting between January 2026 and April 2028.
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537 Cruises (700 Cruise Departures)
12 Day Miami to Miami with Silversea
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Shadow
Departure: 07 November 2026
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Montserrat
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,880
Balcony
$5,840
Suite
$6,380
From
US$4,880
Save 1,220
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
8 Day A Journey Through Shimmering Island History & Mesmerisingly Cultures with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 27 November 2027
Visit: Puerto Rico, Saint Barthelemy, Virgin Islands, Dominican Republic, Bahamas, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,520
From
US$3,915
Per Person
View Trip
19 Day An Extended Journey Through Caribbean Echoes, Balmy Breezes & Emerald Landscapes with Explora Journeys
Cruise

19 Days (18 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 12 February 2026
Visit: USA, Dominican Republic, Dominica, Barbados (+7 more), Guadeloupe, Virgin Islands, Puerto Rico, Aruba, Curacao, Bonaire, Saint Martin
A Suite Invitation
Inside
-
Oceanview
-
Balcony
-
Suite
$11,585
From
US$11,585
Per Person
View Trip
11 Day Treasures Of Belize with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Grandeur
Departure: 09 December 2026
Visit: USA, Mexico, Belize, Honduras, Jamaica, Cayman Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,978
Suite
$7,615
From
US$6,978
Save 12,420
Per Person
View Trip
18 Day A Grand Journey Through Balmy Shores & Enchanting Nature to Panama’s Wonders with Explora Journeys
Cruise

18 Days (17 Nights) San Juan to Panama City
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 05 April 2027
Visit: Puerto Rico, Saint Barthelemy, Montserrat, Saint Kitts and Nevis (+6 more), USA, Jamaica, Curacao, Aruba, Colombia, Panama
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$8,995
Suite
$10,395
From
US$8,995
Per Person
View Trip
15 Day Discover Eastern Caribbean & Grenadines with Emerald Cruises
Cruise

15 Days (14 Nights) Bridgetown to Marigot
Cruise Line: Emerald Cruises
Ships: Emerald Sakara, Emerald Azzurra
Departures: Mar 2026 to Nov 2026
Visit: Barbados, Saint Vincent, Saint Lucia, Guadeloupe (+5 more), Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Anguilla, Saint Martin
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$27,611
From
US$27,611
Save 34,102
Per Person
View Trip
8 Day A Journey Through Historical Gems & Idyllic Coastlines with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departures: Mar 2028 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Guadeloupe, Saint Martin, Bahamas, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,520
From
US$3,915
Per Person
View Trip
16 Day Sapphire Sea Dreams with Regent Seven Seas
Cruise

16 Days (15 Nights) Miami to Galveston
Cruise Line: Regent Seven Seas
Ship: Seven Seas Splendor
Departure: 15 November 2026
Visit: USA, Curacao, Aruba, Bonaire (+4 more), Jamaica, Cayman Islands, Honduras, Mexico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$11,100
Suite
$12,374
From
US$11,100
Save 18,498
Per Person
View Trip
9 Day Bridgetown to Bridgetown with Silversea
Cruise

9 Days (8 Nights) Bridgetown to Bridgetown
Cruise Line: Silversea
Ship: Silver Spirit
Departure: 19 December 2026
Visit: Barbados, Saint Vincent, Martinique, Dominica, Saint Kitts and Nevis, Virgin Islands, Saint Lucia
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$3,600
Balcony
$4,200
Suite
$3,900
From
US$3,600
Save 2,400
Per Person
View Trip
8 Day West Indies Island Hopping with Emerald Cruises
New ReleaseCruise

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 27 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis
Wave Offer
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$5,303
Balcony
-
Suite
$7,073
From
US$5,303
Save 7,687
Per Person
View Trip
13 Day Prestige Isles with Regent Seven Seas
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 05 March 2027
Visit: USA, Virgin Islands, Saint Kitts and Nevis, Dominica, Saint Lucia, Barbados, Guadeloupe
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,330
Suite
$9,575
From
US$9,330
Save 15,668
Per Person
View Trip
8 Day A Journey Through the Caribbean's Elegant Charm & Vibrant Soul with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 22 January 2028
Visit: Puerto Rico, Saint Barthelemy, Virgin Islands, Dominican Republic, Bahamas, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,915
Suite
$4,520
From
US$3,915
Per Person
View Trip
11 Day Season To Cheer with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 18 December 2027
Visit: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis, Dominica, Antigua and Barbuda, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,977
Suite
$7,369
From
US$6,977
Save 13,221
Per Person
View Trip
8 Day A Journey into Tropical Utopia & Art Deco Flair with Explora Journeys
Cruise

8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 02 March 2026
Visit: Puerto Rico, Antigua and Barbuda, Anguilla, Virgin Islands, USA
A Suite Invitation
Inside
-
Oceanview
-
Balcony
$3,825
Suite
$4,310
From
US$3,825
Per Person
View Trip
9 Day Southern Caribbean Gems with Seabourn
Cruise

9 Days (8 Nights) Miami to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 20 November 2026
Visit: USA, Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Saint Vincent, Barbados
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,763
Suite
$7,095
From
US$3,763
Save 61
Per Person
View Trip
11 Day Island Odyssey: Bahamas to the Grenadine with Scenic
New ReleaseCruise

11 Days (10 Nights) Nassau to Bridgetown
Cruise Line: Scenic
Ship: Scenic Eclipse I
Departure: 10 October 2027
Visit: Bahamas, Turks and Caicos Islands, Virgin Islands, Saint Barthelemy, Martinique, Saint Vincent, Barbados
Early Booking Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$9,018
Suite
$9,746
From
US$9,018
Save 12,672
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
15 Day Discover the Pearls of the Caribbean with Emerald Cruises
New ReleaseCruise

15 Days (14 Nights) Bridgetown to Philipsburg
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Nov 2027 to Apr 2028
Visit: Barbados, Saint Lucia, Guadeloupe, Antigua and Barbuda (+6 more), Saint Kitts and Nevis, Saint Barthelemy, Anguilla, Saint Martin, Bonaire, Virgin Islands
Fly Free Economy
Fly Free Premium Economy
Exclusive Savings
Inside
-
Oceanview
$11,169
Balcony
-
Suite
$14,564
From
US$11,169
Save 12,326
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
10 Day Colours of the Caribbean: Antigua to San Juan with Emerald Cruises
New ReleaseCruise

10 Days (9 Nights) Saint John's to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Kaia
Departure: 11 December 2027
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Guadeloupe, Dominica, Saint Kitts and Nevis, Antigua and Barbuda
Wave Offer
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$5,946
Balcony
-
Suite
$8,226
From
US$5,946
Save 8,544
Per Person
View Trip
12 Day Miami to Miami with Silversea
Cruise

12 Days (11 Nights) Miami to Miami
Cruise Line: Silversea
Ship: Silver Ray
Departure: 16 January 2027
Visit: USA, Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Guadeloupe
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,480
Suite
$8,990
From
US$6,480
Save 1,620
Per Person
View Trip
8 Day Treasures Of Aruba, Bonaire & Curacao with Seabourn
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 02 January 2027
Visit: Barbados, Saint Lucia, Curacao, Aruba, Bonaire
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,012
Suite
$8,343
From
US$4,012
Save 67
Per Person
View Trip
11 Day San Juan to Miami, Fl with Silversea
Cruise

11 Days (10 Nights) San Juan to Miami
Cruise Line: Silversea
Ship: Silver Dawn
Departure: 22 February 2028
Visit: Puerto Rico, Virgin Islands, Saint Barthelemy, Dominica (+4 more), Martinique, Antigua and Barbuda, Saint Kitts and Nevis, USA
All-Inclusive Fare
Exclusive Savings
Inside
-
Oceanview
$4,240
Balcony
$4,800
Suite
$9,540
From
US$4,240
Save 1,060
Per Person
View Trip
13 Day Antillean Island Sojourn with Oceania Cruises
Cruise

13 Days (12 Nights) Miami to Miami
Cruise Line: Oceania Cruises
Ship: Oceania Vista
Departure: 25 November 2026
Visit: USA, Virgin Islands, Saint Martin, Saint Barthelemy, Martinique, Guadeloupe, Antigua and Barbuda
Upgrade Your Experience
Your World Inclusions
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$4,636
Suite
$7,012
From
US$4,636
Save 4,862
Per Person
View Trip
8 Day Eastern Caribbean with St. Barths with Emerald Cruises
Cruise

8 Days (7 Nights) Philipsburg to Bridgetown
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departures: Dec 2027 to Apr 2028
Visit: Saint Martin, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis (+4 more), Antigua and Barbuda, Guadeloupe, Saint Lucia, Barbados
Early Payment Discount
Exclusive Savings
Inside
-
Oceanview
$4,607
Balcony
-
Suite
$6,305
From
US$4,607
Save 7,140
Per Person
View Trip
11 Day Bahamian Breeze with Regent Seven Seas
Cruise

11 Days (10 Nights) Miami to Miami
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 07 January 2028
Visit: USA, Saint Martin, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy, Virgin Islands
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,171
Suite
$7,563
From
US$7,171
Save 13,427
Per Person
View Trip
8 Day Grenadines & Windwards yachting with Emerald Cruises
Cruise

8 Days (7 Nights) Bridgetown to Bridgetown
Cruise Line: Emerald Cruises
Ships: Emerald Azzurra, Emerald Sakara
Departures: Mar 2026 to Apr 2028
Visit: Barbados, Grenada, Saint Vincent
Early Payment Discount
Wave Offer
Exclusive Savings
Inside
-
Oceanview
$3,678
Balcony
-
Suite
$5,036
From
US$3,678
Save 18,289
Per Person
View Trip
15 Day Yachtsman's Island Jewels with Seabourn
Cruise

15 Days (14 Nights) Philipsburg to Bridgetown
Cruise Line: Seabourn
Ship: Seabourn Ovation
Departure: 07 March 2026
Visit: Saint Martin, Virgin Islands, Saint Kitts and Nevis, Martinique (+6 more), Saint Vincent, Grenada, Barbados, Guadeloupe, Dominica, Saint Lucia
Explore More
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,521
Suite
$20,507
From
US$7,521
Save 128
Per Person
View Trip
9 Day Splendours of the Caribbean with Scenic
New ReleaseCruise

9 Days (8 Nights) Saint John's to Bridgetown
Cruise Line: Scenic
Ship: Scenic Eclipse II
Departure: 15 October 2027
Visit: Antigua and Barbuda, Saint Barthelemy, Virgin Islands, Montserrat (+5 more), Martinique, Saint Lucia, Saint Vincent, Trinidad and Tobago, Barbados
Early Booking Savings
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$7,917
Suite
$8,208
From
US$7,917
Save 11,473
Per Person
View Trip
Results: 301-330 of 537

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