Filter Results
51 Cruises (56 Departures)
51 Cruises (56 Departures)
Departures
Duration
5 Days
18 Days
End City
Ship Size
Ship Features
Operators
Price
$800pp
$22,140pp
Countries
Cruise
(1)
Southern Caribbean Cruise
11 Days (10 Nights) San Juan to Miami
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 06 March 2027
Visits: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda +4 more, Barbados, Saint Lucia, Dominica, USA
Exclusive Savings
Inside
$1,871
Oceanview
$2,227
Balcony
-
Suite
$7,355
From (Per Person)
A$1,871
Save 1,022
Per Person
Cruise
(4)
Southern Caribbean Cruise: St.barts, Antigua & Tortola
10 Days (9 Nights) San Juan to Miami
Cruise Line: Azamara
Ship: Azamara Journey
Departure: 05 January 2027
Visits: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Martin, Antigua and Barbuda, Saint Kitts and Nevis, USA
Azamara Always Included
Exclusive Savings
Inside
$3,159
Oceanview
$3,904
Balcony
$4,668
Suite
$7,167
From (Per Person)
A$3,159
Save 50
Per Person
Cruise
(2)
Eastern Caribbean: San Juan to Miami
6 Days (5 Nights) San Juan to Miami
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 10 April 2027
Visits: Puerto Rico, Turks and Caicos Islands, Bahamas, USA
Inside
$829
Oceanview
$920
Balcony
$1,134
Suite
$3,565
From (Per Person)
A$829
Per Person
Cruise
(5)
Eastern & Southern Caribbean Cruise: Grenada, Barbados & Aruba
18 Days (17 Nights) San Juan to Miami
Cruise Line: Azamara
Ship: Azamara Quest
Departure: 19 December 2027
Visits: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica +10 more, Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Bonaire, Curacao, Aruba, Dominican Republic, Bahamas, USA
Azamara Always Included
Exclusive Savings
Inside
$9,156
Oceanview
$11,253
Balcony
$13,850
Suite
$21,102
From (Per Person)
A$9,156
Save 153
Per Person
Cruise
(12)
Southern Caribbean with Aruba
8 Days (7 Nights) San Juan to Fort Lauderdale
Cruise Line: Princess
Ship: Crown Princess
Departure: 28 March 2027
Visits: Puerto Rico, Saint Martin, Aruba, Curacao, USA
Exclusive Savings
Inside
$993
Oceanview
$1,126
Balcony
$1,963
Suite
$2,795
From (Per Person)
A$993
Per Person
Cruise
(1)
A Journey to Island Rhythms & Tranquil Bahamian Bliss
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departures: Jan 2028
Visits: Puerto Rico, Virgin Islands, Guadeloupe, Saint Barthelemy, Bahamas, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
(1)
A Journey of Tropical Spirits & the Colourful Beauty of the Antilles
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 19 December 2027
Visits: Puerto Rico, Virgin Islands, Guadeloupe, Saint Barthelemy, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,262
From (Per Person)
A$7,262
Save 148
Per Person
Cruise
(1)
A Journey Through Beguiling Tropical Elegance To Vibrant Island Delights
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 27 February 2028
Visits: Puerto Rico, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Bahamas, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
(1)
San Juan to Miami, Fl
9 Days (8 Nights) San Juan to Miami
Cruise Line: Silversea
Ship: Silver Nova
Departure: 29 December 2026
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica, Antigua and Barbuda, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$6,880
Suite
$12,348
From (Per Person)
A$6,880
Save 4,820
Per Person
Cruise
(1)
A Journey Through Tropical Utopia & Rhythmic Streets
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 12 March 2028
Visits: Puerto Rico, Virgin Islands, Saint Barthelemy, Bahamas, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
(1)
Southern Caribbean with ABC Islands
8 Days (7 Nights) San Juan to Fort Lauderdale
Cruise Line: Princess
Ship: Emerald Princess
Departure: 26 March 2028
Visits: Puerto Rico, Curacao, Aruba, Bonaire, USA
Exclusive Savings
Inside
$1,201
Oceanview
$1,506
Balcony
$2,206
Suite
$3,067
From (Per Person)
A$1,201
Per Person
Cruise
An Extended Journey of Dazzling Skylines & Wildlife Exploration
17 Days (16 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 04 January 2027
Visits: Puerto Rico, Saint Martin, Antigua and Barbuda, Montserrat, Virgin Islands, USA, Dominican Republic
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$13,965
From (Per Person)
A$13,965
Save 285
Per Person
Cruise
A Journey Through Captivating Caribbean Culture & Sunlit Shores
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 12 February 2027
Visits: Puerto Rico, Virgin Islands, Antigua and Barbuda, Guadeloupe, Dominican Republic, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,830
From (Per Person)
A$7,830
Save 160
Per Person
Cruise
A Journey Through Caribbean Gems & Multi-coloured Coasts
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 13 December 2026
Visits: Puerto Rico, Anguilla, Antigua and Barbuda, Saint Kitts and Nevis, Turks and Caicos Islands, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,291
From (Per Person)
A$7,291
Save 149
Per Person
Cruise
A Journey Through Historical Gems & Idyllic Coastlines
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departures: Mar 2028 to Apr 2028
Visits: Puerto Rico, Virgin Islands, Guadeloupe, Saint Martin, Bahamas, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
A Journey of Caribbean Enchantment & Tranquil Shores
9 Days (8 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 13 January 2027
Visits: Puerto Rico, Saint Martin, Guadeloupe, Grenada, Saint Lucia, Dominican Republic, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$9,369
From (Per Person)
A$9,369
Save 191
Per Person
Cruise
An Extended Journey Of Caribbean Celebrations & Tropical Idylls
18 Days (17 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 28 December 2026
Visits: Puerto Rico, Antigua and Barbuda, Guadeloupe, Virgin Islands +4 more, Dominican Republic, USA, Saint Barthelemy, Saint Kitts and Nevis
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$19,874
From (Per Person)
A$19,874
Save 406
Per Person
Cruise
A Journey Of Spectacular Festivities & Caribbean Wonders
10 Days (9 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 28 December 2026
Visits: Puerto Rico, Antigua and Barbuda, Guadeloupe, Virgin Islands, Dominican Republic, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$9,526
From (Per Person)
A$9,526
Save 194
Per Person
Cruise
A Journey Through Shimmering Island History & Mesmerisingly Cultures
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 27 November 2027
Visits: Puerto Rico, Saint Barthelemy, Virgin Islands, Dominican Republic, Bahamas, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,934
From (Per Person)
A$5,934
Save 121
Per Person
Cruise
San Juan to Miami, Fl
9 Days (8 Nights) San Juan to Miami
Cruise Line: Silversea
Ship: Silver Ray
Departure: 26 December 2027
Visits: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique, Saint Kitts and Nevis, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$8,232
Suite
$16,660
From (Per Person)
A$8,232
Save 3,768
Per Person
Cruise
A Journey of Intimate Island Bliss & Caribbean Breeze
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 05 February 2028
Visits: Puerto Rico, Saint Barthelemy, Virgin Islands, Bahamas, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
A Journey Through The Caribbean's Rich History & Palm-shaded Paradise
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departures: Mar 2028 to Apr 2028
Visits: Puerto Rico, Virgin Islands, Dominican Republic, USA, Bahamas
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
An Extended Journey Through Wild Beauty and Tropical Festivities
16 Days (15 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 13 December 2026
Visits: Puerto Rico, Anguilla, Antigua and Barbuda, Saint Kitts and Nevis +6 more, Turks and Caicos Islands, USA, Jamaica, Dominican Republic, Virgin Islands, Saint Martin
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$16,582
From (Per Person)
A$16,582
Save 338
Per Person
Cruise
A Journey Through A Caribbean Tapestry Of Serenity & Splendour
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 November 2026
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Turks and Caicos Islands, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,291
From (Per Person)
A$7,291
Save 149
Per Person
Cruise
San Juan To Ft. Lauderdale
5 Days (4 Nights) San Juan to Fort Lauderdale
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 02 January 2028
Visits: Puerto Rico, Saint Martin, USA
Exclusive Savings
Inside
$822
Oceanview
$853
Balcony
$955
Suite
$3,986
From (Per Person)
A$822
Save 455
Per Person
Cruise
A Journey Of Blissful Escapes & Island Splendour
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 15 November 2026
Visits: Puerto Rico, Anguilla, Antigua and Barbuda, Virgin Islands, Dominican Republic, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,291
From (Per Person)
A$7,291
Save 149
Per Person
Cruise
A Journey Through Caribbean Jewels
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 29 April 2028
Visits: Puerto Rico, Virgin Islands, Guadeloupe, Saint Kitts and Nevis, Saint Martin, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
A Journey Of Caribbean Delicacies & Idyllic Islands
8 Days (7 Nights) San Juan to Miami
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 04 January 2027
Visits: Puerto Rico, Saint Martin, Antigua and Barbuda, Montserrat, Virgin Islands, USA
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$6,282
From (Per Person)
A$6,282
Save 128
Per Person
Cruise
An Extended Journey into Island Bliss & Lively Celebrations
16 Days (15 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 20 December 2026
Visits: Puerto Rico, Saint Kitts and Nevis, Virgin Islands, Saint Barthelemy, Anguilla, USA, Dominican Republic
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$19,492
From (Per Person)
A$19,492
Save 398
Per Person
Cruise
An Extended Journey Through Golden Shores & Island Grace
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 November 2026
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy +4 more, Turks and Caicos Islands, USA, Antigua and Barbuda, Guadeloupe
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$14,308
From (Per Person)
A$14,308
Save 292
Per Person
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