Filter Results
169 Cruises (323 Departures)
169 Cruises (323 Departures)
Departures
Duration
6 Days
25 Days
Ship Size
Ship Features
Operators
Price
$800pp
$28,620pp
Countries
Cruise
(1)
West Indies Explorer
11 Days (10 Nights) San Juan to San Juan
Operator: Viking
Departures: Nov 2026 to Jan 2029
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia +4 more, Barbados, Dominica, Antigua and Barbuda, Sint Maarten
Exclusive Savings
Balcony
$6,610
Suite
$9,354
From (Per Person)
A$6,610
Save 1,385
Per Person
Cruise
(1)
Southern Caribbean Adventurer
15 Days (14 Nights) San Juan to San Juan
Operator: Princess
Ship: Emerald Princess
Departure: 05 December 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda +5 more, Saint Lucia, Barbados, Saint Kitts and Nevis, Martinique, Dominica
Exclusive Savings
Inside
$2,462
Oceanview
$2,763
Balcony
$3,373
Suite
$4,303
From (Per Person)
A$2,462
Per Person
Cruise
(1)
Southern Caribbean with Barbados and St. Lucia Holiday
8 Days (7 Nights) San Juan to San Juan
Operator: Princess
Ship: Emerald Princess
Departure: 21 November 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Dominica, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,231
Oceanview
$1,486
Balcony
$1,785
Suite
$2,795
From (Per Person)
A$1,231
Per Person
Cruise
(1)
Southern Caribbean Cruise From San Juan To San Juan
8 Days (7 Nights) San Juan to San Juan
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 14 February 2027
Visits: Puerto Rico, Virgin Islands, Barbados, Saint Kitts and Nevis, Saint Martin
Just Cruise Fare
Exclusive Savings
Inside
$2,182
Oceanview
$2,330
Balcony
$2,628
Suite
$3,804
From (Per Person)
A$2,182
Per Person
Cruise
(1)
Southern Caribbean Cruise From San Juan To San Juan
8 Days (7 Nights) San Juan to San Juan
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 19 February 2028
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Martin
Just Cruise Fare
Exclusive Savings
Inside
$2,211
Oceanview
$2,523
Balcony
$2,836
Suite
$4,176
From (Per Person)
A$2,211
Per Person
Cruise
(1)
Southern Caribbean Holiday
9 Days (8 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 31 December 2027
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia, Antigua and Barbuda, Saint Vincent
Exclusive Savings
Inside
$2,001
Oceanview
$2,378
Balcony
$3,837
Suite
$4,581
From (Per Person)
A$2,001
Save 1,068
Per Person
Cruise
(2)
Southern Caribbean Halloween Cruise
8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visits: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Inside
$1,717
Oceanview
$1,820
Balcony
$1,922
Suite
$5,376
From (Per Person)
A$1,717
Per Person
Cruise
(1)
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 27 November 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Saint Lucia, Saint Kitts and Nevis
Exclusive Savings
Inside
$1,151
Oceanview
$1,233
Balcony
$1,979
Suite
$2,367
From (Per Person)
A$1,151
Save 675
Per Person
Cruise
(1)
Southern Caribbean Adventurer
15 Days (14 Nights) San Juan to San Juan
Operator: Princess
Ship: Emerald Princess
Departure: 21 November 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Dominica +4 more, Saint Lucia, Barbados, Saint Kitts and Nevis, Grenada
Exclusive Savings
Inside
$2,482
Oceanview
$3,013
Balcony
$3,373
Suite
$4,957
From (Per Person)
A$2,482
Per Person
Cruise
(5)
Caribbean Holiday Cruise: San Juan, St. Barts & Curacao
19 Days (18 Nights) San Juan to San Juan
Operator: Azamara
Ship: Azamara Journey
Departure: 18 December 2026
Visits: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy +8 more, Martinique, Saint Vincent, Trinidad and Tobago, Barbados, Aruba, Curacao, Saint Lucia, Saint Kitts and Nevis
Azamara Always Included
Exclusive Savings
Inside
-
Oceanview
$6,879
Balcony
$9,182
Suite
$12,632
From (Per Person)
A$6,879
Save 110
Per Person
Cruise
(12)
Southern Caribbean with Barbados and St. Lucia
8 Days (7 Nights) San Juan to San Juan
Operator: Princess
Ship: Crown Princess
Departure: 17 January 2027
Visits: Puerto Rico, Saint Martin, Martinique, Grenada, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,557
Oceanview
$1,638
Balcony
$2,795
Suite
$3,636
From (Per Person)
A$1,557
Per Person
Cruise
(1)
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Operator: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 30 January 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$1,006
Oceanview
$1,060
Balcony
$2,030
Suite
$2,917
From (Per Person)
A$1,006
Save 611
Per Person
Cruise
(1)
Southern Caribbean Cruise From San Juan To San Juan
8 Days (7 Nights) San Juan to San Juan
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 07 March 2027
Visits: Puerto Rico, Virgin Islands, Aruba, Curacao
Just Cruise Fare
Exclusive Savings
Inside
$2,405
Oceanview
$2,479
Balcony
$2,851
Suite
$3,447
From (Per Person)
A$2,405
Per Person
Cruise
(1)
Southern Caribbean From San Juan To San Juan
8 Days (7 Nights) San Juan to San Juan
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 13 December 2026
Visits: Puerto Rico, Saint Martin, Saint Kitts and Nevis, Barbados, Saint Lucia, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$2,092
Oceanview
$2,122
Balcony
$2,420
Suite
$2,940
From (Per Person)
A$2,092
Per Person
Cruise
(1)
Southern Caribbean Cruise From San Juan To San Juan
8 Days (7 Nights) San Juan to San Juan
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 11 December 2027
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Martin, Barbados
Just Cruise Fare
Exclusive Savings
Inside
$2,077
Oceanview
$2,345
Balcony
$2,687
Suite
$3,894
From (Per Person)
A$2,077
Per Person
Cruise
(1)
Southern Caribbean Cruise From San Juan To San Juan
8 Days (7 Nights) San Juan to San Juan
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 20 December 2026
Visits: Puerto Rico, Aruba, Curacao, Virgin Islands
Just Cruise Fare
Exclusive Savings
Inside
$1,958
Oceanview
$2,077
Balcony
$2,301
Suite
$2,851
From (Per Person)
A$1,958
Per Person
Cruise
(1)
Southern Caribbean Adventurer Holiday
15 Days (14 Nights) San Juan to San Juan
Operator: Princess
Ship: Emerald Princess
Departure: 26 December 2027
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica +5 more, Grenada, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Exclusive Savings
Inside
$2,640
Oceanview
$3,026
Balcony
$3,373
Suite
$5,551
From (Per Person)
A$2,640
Per Person
Cruise
(2)
Southern Caribbean & Aruban Nights
9 Days (8 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 29 January 2027
Visits: Puerto Rico, Aruba, Curacao, Bonaire, Martinique, Saint Martin
Inside
$2,312
Oceanview
$2,428
Balcony
$2,544
Suite
$6,957
From (Per Person)
A$2,312
Per Person
Cruise
(1)
Southern Caribbean From San Juan To San Juan
8 Days (7 Nights) San Juan to San Juan
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departures: Jan 2028
Visits: Puerto Rico, Virgin Islands, Aruba, Curacao
Just Cruise Fare
Exclusive Savings
Inside
$2,121
Oceanview
$2,434
Balcony
$2,777
Suite
$4,087
From (Per Person)
A$2,121
Per Person
Cruise
(12)
Southern Caribbean Adventurer
15 Days (14 Nights) San Juan to San Juan
Operator: Princess
Ship: Crown Princess
Departure: 24 January 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda +5 more, Saint Lucia, Barbados, Guadeloupe, Dominica, Grenada
Exclusive Savings
Inside
$2,135
Oceanview
$2,492
Balcony
$4,779
Suite
$6,095
From (Per Person)
A$2,135
Per Person
Cruise
(1)
Southern Caribbean Adventurer
15 Days (14 Nights) San Juan to San Juan
Operator: Princess
Ship: Emerald Princess
Departure: 09 January 2028
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica +5 more, Grenada, Barbados, Saint Martin, Antigua and Barbuda, Saint Lucia
Exclusive Savings
Inside
$2,244
Oceanview
$2,763
Balcony
$3,096
Suite
$4,640
From (Per Person)
A$2,244
Per Person
Cruise
(12)
Southern Caribbean Adventurer
15 Days (14 Nights) San Juan to San Juan
Operator: Princess
Ship: Crown Princess
Departure: 07 February 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda +4 more, Dominica, Barbados, Saint Kitts and Nevis, Grenada
Exclusive Savings
Inside
$2,214
Oceanview
$2,705
Balcony
$4,016
Suite
$7,015
From (Per Person)
A$2,214
Per Person
Cruise
(2)
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 06 March 2027
Visits: Puerto Rico, Saint Martin, Barbados, Saint Lucia, Antigua and Barbuda, Virgin Islands
Inside
$1,616
Oceanview
$1,717
Balcony
$1,819
Suite
$5,782
From (Per Person)
A$1,616
Per Person
Cruise
(1)
Southern Caribbean Cruise From San Juan To San Juan
8 Days (7 Nights) San Juan to San Juan
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 04 December 2027
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Barbados, Saint Lucia, Saint Martin
Just Cruise Fare
Exclusive Savings
Inside
$2,077
Oceanview
$2,301
Balcony
$2,627
Suite
$3,803
From (Per Person)
A$2,077
Per Person
Cruise
(12)
Southern Caribbean with Barbados and St. Lucia Holiday
8 Days (7 Nights) San Juan to San Juan
Operator: Princess
Departures: Dec 2026 to Dec 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,142
Oceanview
$1,362
Balcony
$1,766
Suite
$2,756
From (Per Person)
A$1,142
Save 21
Per Person
Cruise
(12)
Southern Caribbean Adventurer
15 Days (14 Nights) San Juan to San Juan
Operator: Princess
Ship: Crown Princess
Departure: 28 February 2027
Visits: Puerto Rico, Saint Martin, Martinique, Dominica +5 more, Grenada, Barbados, Virgin Islands, Antigua and Barbuda, Saint Lucia
Exclusive Savings
Inside
$2,066
Oceanview
$2,145
Balcony
$3,799
Suite
$6,046
From (Per Person)
A$2,066
Per Person
Cruise
(2)
Southern Caribbean Cruise
9 Days (8 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 19 March 2027
Visits: Puerto Rico, Virgin Islands, Barbados, Saint Vincent, Dominica, Saint Martin
Inside
$1,382
Oceanview
$1,499
Balcony
$1,731
Suite
$6,609
From (Per Person)
A$1,382
Per Person
Cruise
(2)
Southern Caribbean & Aruban Nights
8 Days (7 Nights) San Juan to San Juan
Operator: Virgin Voyages
Ship: Scarlet Lady
Departures: Jan 2028 to Mar 2028
Visits: Puerto Rico, Aruba, Saint Lucia, Antigua and Barbuda, Saint Martin
Inside
$1,109
Oceanview
$1,312
Balcony
$1,819
Suite
$5,590
From (Per Person)
A$1,109
Per Person
Cruise
(12)
Southern Caribbean with Barbados and St. Thomas
8 Days (7 Nights) San Juan to San Juan
Operator: Princess
Ship: Crown Princess
Departure: 31 January 2027
Visits: Puerto Rico, Virgin Islands, Guadeloupe, Dominica, Grenada, Barbados
Exclusive Savings
Inside
$993
Oceanview
$1,250
Balcony
$2,102
Suite
$2,527
From (Per Person)
A$993
Per Person
Cruise
(1)
Southern Caribbean with Barbados and St. Lucia
8 Days (7 Nights) San Juan to San Juan
Operator: Princess
Ship: Emerald Princess
Departure: 13 February 2028
Visits: Puerto Rico, Virgin Islands, Saint Martin, Dominica, Saint Lucia, Barbados
Exclusive Savings
Inside
$1,142
Oceanview
$1,667
Balcony
$1,884
Suite
$3,013
From (Per Person)
A$1,142
Per Person
No trips found. Try adjusting the search filters.
