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49 Cruises (58 Departures)
49 Cruises (58 Departures)
Departures
Duration
4 Days
25 Days
Start City
Ship Size
Ship Features
Operators
Price
$1,000pp
$20,280pp
Countries
Cruise
(1)
Southern Caribbean with Curacao
8 Days (7 Nights) Fort Lauderdale to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 14 November 2027
Visits: USA, Jamaica, Aruba, Curacao, Puerto Rico
Exclusive Savings
Inside
$1,271
Oceanview
$1,334
Balcony
$1,716
Suite
$2,429
From (Per Person)
A$1,271
Per Person
Cruise
(12)
Southern Caribbean Islander Holiday
9 Days (8 Nights) Fort Lauderdale to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departure: 19 December 2026
Visits: USA, Aruba, Curacao, Antigua and Barbuda, Virgin Islands, Puerto Rico
Exclusive Savings
Inside
$1,043
Oceanview
$1,030
Balcony
$1,529
Suite
$2,449
From (Per Person)
A$1,030
Per Person
Cruise
(1)
Southern Caribbean Adventurer Holiday
15 Days (14 Nights) Fort Lauderdale to San Juan
Cruise Line: Princess
Ship: Emerald Princess
Departure: 14 November 2027
Visits: USA, Jamaica, Aruba, Curacao +6 more, Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Saint Lucia, Barbados
Exclusive Savings
Inside
$2,680
Oceanview
$2,722
Balcony
$3,393
Suite
$5,205
From (Per Person)
A$2,680
Per Person
Cruise
(2)
Bermuda & Caribbean: NYC to San Juan
13 Days (12 Nights) New York to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 19 October 2026
Visits: USA, Bermuda, Bahamas, Virgin Islands, Saint Martin, Puerto Rico
Inside
$1,523
Oceanview
$1,695
Balcony
$1,866
Suite
$7,171
From (Per Person)
A$1,523
Per Person
Cruise
(1)
A Journey Into Timeless Marvels & Historical Tales of the West Indies
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 12 December 2027
Visits: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Saint Martin, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
(1)
A Journey Across Oceanic Gems & The Unresistible Caribbean Charm
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 05 March 2028
Visits: USA, Anguilla, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
(1)
A Journey into Dominican Charm & Caribbean Splendour
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 30 January 2028
Visits: USA, Dominican Republic, Virgin Islands, Anguilla, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
(4)
Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen
10 Days (9 Nights) New York to San Juan
Cruise Line: Azamara
Departures: Oct 2026 to Oct 2027
Visits: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Exclusive Savings
Inside
$2,579
Oceanview
$2,749
Balcony
$3,785
Suite
$6,081
From (Per Person)
A$2,579
Save 40
Per Person
Cruise
(1)
A Journey from Dominican Rhythms & Tranquil Bahamian Bliss
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 09 January 2028
Visits: USA, Dominican Republic, Virgin Islands, Saint Martin, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
(1)
Eastern Caribbean Cruise From Orlando To San Juan
4 Days (3 Nights) Orlando to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 12 November 2026
Visits: USA, Dominican Republic, Puerto Rico
Just Cruise Fare
Exclusive Savings
Inside
$1,085
Oceanview
$1,085
Balcony
$1,129
Suite
$1,159
From (Per Person)
A$1,085
Per Person
Cruise
(1)
Southern Caribbean Cruise From New York To San Juan
11 Days (10 Nights) New York to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 03 November 2027
Visits: USA, Bermuda, Virgin Islands, Saint Kitts and Nevis +4 more, Barbados, Antigua and Barbuda, Saint Martin, Puerto Rico
Just Cruise Fare
Exclusive Savings
Inside
$3,430
Oceanview
$3,654
Balcony
$4,323
Suite
$5,664
From (Per Person)
A$3,430
Per Person
Cruise
(5)
Bermuda & Eastern Caribbean Cruise: Tortola, Barbados & Saint Kitts
25 Days (24 Nights) New York to San Juan
Cruise Line: Azamara
Ship: Azamara Quest
Departure: 28 October 2027
Visits: USA, Bermuda, Saint Martin, Virgin Islands +10 more, Puerto Rico, Antigua and Barbuda, Martinique, Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis
Azamara Always Included
Exclusive Savings
Inside
$8,157
Oceanview
$9,832
Balcony
$12,126
Suite
$19,191
From (Per Person)
A$8,157
Per Person
Cruise
(1)
A Journey of Underwater Jewels & Captivating New Year's Eve Celebration
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 26 December 2027
Visits: USA, Dominican Republic, Virgin Islands, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$8,060
From (Per Person)
A$8,060
Save 165
Per Person
Cruise
An Extended Journey of Tropical Harmony & Natural Wonders
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 15 November 2026
Visits: Puerto Rico, Anguilla, Antigua and Barbuda, Virgin Islands +4 more, Dominican Republic, USA, Guadeloupe, Saint Martin
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$13,485
From (Per Person)
A$13,485
Save 275
Per Person
Cruise
A Journey Through Beguiling Caribbean Coastlines & Lush Landscapes
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 08 November 2026
Visits: USA, Turks and Caicos Islands, Dominican Republic, Virgin Islands, Saint Barthelemy, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,747
From (Per Person)
A$7,747
Save 158
Per Person
Cruise
An Extended Journey Into Island Delights, Hidden Coves & Chic Coastlines
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 01 November 2026
Visits: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy +4 more, Anguilla, USA, Turks and Caicos Islands, Dominican Republic
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$15,161
From (Per Person)
A$15,161
Save 309
Per Person
Cruise
A Journey Through Secluded Isles & Caribbean Havens
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 05 February 2027
Visits: USA, Saint Martin, Saint Barthelemy, Saint Kitts and Nevis, Virgin Islands, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$7,830
From (Per Person)
A$7,830
Save 160
Per Person
Cruise
A Journey Of Tropical Festivities & Dazzling Island Beauty
9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 20 December 2026
Visits: USA, Jamaica, Dominican Republic, Virgin Islands, Saint Martin, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$8,938
From (Per Person)
A$8,938
Save 182
Per Person
Cruise
A Journey Through Majestic Island Paradises & Radiant Cultures
9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora IV
Departure: 05 November 2027
Visits: USA, Turks and Caicos Islands, Saint Barthelemy, Guadeloupe, Saint Kitts and Nevis, Virgin Islands, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$6,796
From (Per Person)
A$6,796
Save 139
Per Person
Cruise
Boston To San Juan Cruise
10 Days (9 Nights) Boston to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visits: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$1,661
Oceanview
$1,734
Balcony
$2,078
Suite
$6,287
From (Per Person)
A$1,661
Save 822
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
An Extended Journey Through Ancient Marvels & Glittering Shores
17 Days (16 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 20 January 2027
Visits: USA, Jamaica, Guatemala, Honduras +6 more, Belize, Dominican Republic, Saint Martin, Guadeloupe, Saint Kitts and Nevis, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$14,386
From (Per Person)
A$14,386
Save 294
Per Person
Cruise
Tropical Passage
11 Days (10 Nights) Miami to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Prestige
Departure: 20 March 2027
Visits: USA, Virgin Islands, Dominica, Barbados +4 more, Saint Lucia, Martinique, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$13,379
Suite
$13,801
From (Per Person)
A$13,379
Save 2,241
Per Person
Cruise
An Extended Journey Of Cultural Treasures & Seaside Harmony
16 Days (15 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 05 December 2026
Visits: USA, Mexico, Guatemala, Belize +6 more, Honduras, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Martin, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$13,014
From (Per Person)
A$13,014
Save 266
Per Person
Cruise
A Journey Through Stunning Scenery & Charming Caribbean Culture
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 29 January 2027
Visits: USA, Dominican Republic, Saint Martin, Guadeloupe, Saint Kitts and Nevis, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$6,860
From (Per Person)
A$6,860
Save 140
Per Person
Cruise
Baltimore To San Juan Cruise
11 Days (10 Nights) Baltimore to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departure: 22 October 2026
Visits: USA, Turks and Caicos Islands, Saint Martin, Dominica +4 more, Martinique, Antigua and Barbuda, Virgin Islands, Puerto Rico
Exclusive Savings
Inside
$2,093
Oceanview
-
Balcony
-
Suite
-
From (Per Person)
A$2,093
Save 1,099
Per Person
New ReleaseCruise
Caribbean escapade
8 Days (7 Nights) Miami to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 30 November 2026
Visits: USA, Bahamas, Turks and Caicos Islands, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$6,922
From (Per Person)
A$6,922
Save 4,628
Per Person
Cruise
A Journey Of Sparkling Skies & Bright Beginnings
9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 27 December 2026
Visits: USA, Dominican Republic, Virgin Islands, Saint Kitts and Nevis, Puerto Rico
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$11,201
From (Per Person)
A$11,201
Save 229
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 of Secluded Isles & Coastal Havens
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Explora Journeys
Ship: Explora III
Departure: 29 January 2027
Visits: Puerto Rico, Virgin Islands, Antigua and Barbuda, Turks and Caicos Islands +4 more, USA, Saint Martin, Saint Barthelemy, Saint Kitts and Nevis
Exclusive Savings
Inside
-
Oceanview
-
Balcony
-
Suite
$16,283
From (Per Person)
A$16,283
Save 332
Per Person
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