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57 Cruises (66 Departures)
57 Cruises (66 Departures)
Departures
Duration
4 Days
25 Days
Start City
Ship Size
Ship Features
Operators
Price
$900pp
$22,085pp
Countries
Cruise
(6)
Bermuda & Eastern Caribbean Cruise: Tortola, Barbados & Saint Kitts
25 Days (24 Nights) New York to San Juan
Operator: 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
Exclusive Savings
Inside
$7,751
Oceanview
$9,343
Balcony
$11,522
Suite
$18,234
From (Per Person)
A$7,751
Save 518
Per Person
Cruise
(1)
A Journey Across Oceanic Gems & The Unresistible Caribbean Charm
8 Days (7 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora II
Departure: 05 March 2028
Visits: USA, Anguilla, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
(12)
Southern Caribbean Islander Holiday
9 Days (8 Nights) Fort Lauderdale to San Juan
Operator: Princess
Ship: Crown Princess
Departure: 19 December 2026
Visits: USA, Aruba, Curacao, Antigua and Barbuda, Virgin Islands, Puerto Rico
Exclusive Savings
Inside
$1,024
Oceanview
$1,043
Balcony
$1,529
Suite
$2,152
From (Per Person)
A$1,024
Per Person
Cruise
(1)
A Journey of Underwater Jewels & Captivating New Year's Eve Celebration
8 Days (7 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora II
Departure: 26 December 2027
Visits: USA, Dominican Republic, Virgin Islands, Puerto Rico
Exclusive Savings
Suite
$7,521
From (Per Person)
A$7,521
Save 154
Per Person
Cruise
(2)
Bermuda & Caribbean: NYC to San Juan
13 Days (12 Nights) New York to San Juan
Operator: Virgin Voyages
Ship: Valiant Lady
Departure: 19 October 2026
Visits: USA, Bermuda, Bahamas, Virgin Islands, Saint Martin, Puerto Rico
Inside
$1,550
Oceanview
$1,724
Balcony
$1,898
Suite
$6,254
From (Per Person)
A$1,550
Per Person
Cruise
(1)
Eastern Caribbean Cruise From Orlando To San Juan
4 Days (3 Nights) Orlando to San Juan
Operator: Norwegian Cruise Line
Ship: Norwegian Prima
Departure: 12 November 2026
Visits: USA, Dominican Republic, Puerto Rico
Just Cruise Fare
Exclusive Savings
Inside
$965
Oceanview
$1,010
Balcony
$996
Suite
$1,070
From (Per Person)
A$965
Per Person
Cruise
(1)
Southern Caribbean Adventurer Holiday
15 Days (14 Nights) Fort Lauderdale to San Juan
Operator: Princess
Ship: Emerald Princess
Departure: 14 November 2027
Visits: USA, Jamaica, Aruba, Curacao +6 more, Puerto Rico, Virgin Islands, Saint Martin, Dominica, Saint Lucia, Barbados
Exclusive Savings
Inside
$2,245
Oceanview
$2,708
Balcony
$3,096
Suite
$4,987
From (Per Person)
A$2,245
Per Person
Cruise
(5)
Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen
10 Days (9 Nights) New York to San Juan
Operator: Azamara
Departures: Oct 2026 to Oct 2027
Visits: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Exclusive Savings
Inside
$2,545
Oceanview
$2,945
Balcony
$3,597
Suite
$6,138
From (Per Person)
A$2,545
Save 164
Per Person
Cruise
(1)
A Journey Into Timeless Marvels & Historical Tales of the West Indies
8 Days (7 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora II
Departure: 12 December 2027
Visits: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Saint Martin, Puerto Rico
Exclusive Savings
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
Operator: Explora Journeys
Ship: Explora II
Departure: 30 January 2028
Visits: USA, Dominican Republic, Virgin Islands, Anguilla, Puerto Rico
Exclusive Savings
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
(1)
A Journey from Dominican Rhythms & Tranquil Bahamian Bliss
8 Days (7 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora II
Departure: 09 January 2028
Visits: USA, Dominican Republic, Virgin Islands, Saint Martin, Puerto Rico
Exclusive Savings
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
(1)
Southern Caribbean Cruise From New York To San Juan
11 Days (10 Nights) New York to San Juan
Operator: 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
(1)
Southern Caribbean with Curacao
8 Days (7 Nights) Fort Lauderdale to San Juan
Operator: Princess
Ship: Emerald Princess
Departure: 14 November 2027
Visits: USA, Jamaica, Aruba, Curacao, Puerto Rico
Exclusive Savings
Inside
$1,073
Oceanview
$1,140
Balcony
$1,389
Suite
$2,251
From (Per Person)
A$1,073
Per Person
Cruise
A Journey Through Stunning Scenery & Charming Caribbean Culture
8 Days (7 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora I
Departure: 29 January 2027
Visits: USA, Dominican Republic, Saint Martin, Guadeloupe, Saint Kitts and Nevis, Puerto Rico
Exclusive Savings
Suite
$6,429
From (Per Person)
A$6,429
Save 131
Per Person
New ReleaseCruise
Fort Lauderdale to San Juan
8 Days (7 Nights) Fort Lauderdale to San Juan
Operator: Crystal
Ship: Crystal Serenity
Departure: 12 February 2028
Visits: USA, Virgin Islands, Saint Barthelemy, Dominica, Saint Kitts and Nevis, Puerto Rico
Exclusive Savings
Oceanview
$5,087
Balcony
$5,965
Suite
$6,140
From (Per Person)
A$5,087
Save 613
Per Person
Cruise
An Extended Journey Through Golden Shores & Island Grace
15 Days (14 Nights) San Juan to San Juan
Operator: 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
Suite
$13,411
From (Per Person)
A$13,411
Save 274
Per Person
Cruise
An Extended Journey of Secluded Isles & Coastal Havens
15 Days (14 Nights) San Juan to San Juan
Operator: 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
Suite
$16,072
From (Per Person)
A$16,072
Save 328
Per Person
New ReleaseCruise
New York City to San Juan
10 Days (9 Nights) New York to San Juan
Operator: Crystal
Ship: Crystal Serenity
Departure: 12 October 2027
Visits: USA, Bermuda, Antigua and Barbuda, Guadeloupe, Saint Barthelemy, Puerto Rico
Exclusive Savings
Oceanview
$5,551
Balcony
$6,428
Suite
$6,779
From (Per Person)
A$5,551
Save 1,649
Per Person
Cruise
Tropical Passage
11 Days (10 Nights) Miami to San Juan
Operator: 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
$13,987
Suite
$14,124
From (Per Person)
A$13,987
Save 2,253
Per Person
Cruise
An Extended Journey into Island Bliss & Lively Celebrations
16 Days (15 Nights) San Juan to San Juan
Operator: 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
Suite
$18,409
From (Per Person)
A$18,409
Save 376
Per Person
New ReleaseCruise
Paradise Beaches from the Bahamas to the U.S. Virgin Islands
10 Days (9 Nights) Miami to San Juan
Operator: Emerald Cruises
Ship: Emerald Kaia
Departures: Feb 2029 to Mar 2029
Visits: USA, Bahamas, Turks and Caicos Islands, Puerto Rico, Virgin Islands
Exclusive Savings
Oceanview
$9,884
Suite
$12,182
From (Per Person)
A$9,884
Save 4,161
Per Person
Cruise
A Journey Of Colourful Treasures & Idyllic Island Scenery
8 Days (7 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora III
Departure: 06 December 2026
Visits: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Barthelemy, Puerto Rico
Exclusive Savings
Suite
$6,282
From (Per Person)
A$6,282
Save 128
Per Person
Cruise
A Journey From Glorious Shorelines To Nature's Allure
8 Days (7 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora III
Departure: 28 February 2027
Visits: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Puerto Rico
Exclusive Savings
Suite
$6,909
From (Per Person)
A$6,909
Save 141
Per Person
Cruise
A Journey Of Caribbean Adventure & Shimmering Tropical Harmony
8 Days (7 Nights) Miami to San Juan
Operator: Explora Journeys
Departures: Oct 2026 to Dec 2026
Visits: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Martin, Puerto Rico
Exclusive Savings
Suite
$5,439
From (Per Person)
A$5,439
Save 156
Per Person
Cruise
An Extended Journey Of Caribbean Celebrations & Tropical Idylls
18 Days (17 Nights) San Juan to San Juan
Operator: 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
Suite
$21,643
From (Per Person)
A$21,643
Save 442
Per Person
Cruise
Fort Lauderdale to San Juan
7 Days (6 Nights) Fort Lauderdale to San Juan
Operator: Crystal
Ship: Crystal Symphony
Departure: 28 December 2027
Visits: USA, Cayman Islands, Jamaica, Dominican Republic, Puerto Rico
Exclusive Savings
Oceanview
$5,163
Balcony
$6,655
Suite
$7,006
From (Per Person)
A$5,163
Save 637
Per Person
Cruise
An Extended Journey Through Wild Beauty and Tropical Festivities
16 Days (15 Nights) San Juan to San Juan
Operator: 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
Suite
$16,351
From (Per Person)
A$16,351
Save 334
Per Person
Cruise
A Journey Through Art Deco Wonders & Caribbean Adventures
8 Days (7 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora IV
Departure: 23 December 2027
Visits: USA, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis, Puerto Rico
Exclusive Savings
Suite
$6,453
From (Per Person)
A$6,453
Save 132
Per Person
Cruise
A Journey Through the Vibrant Pulse of the Antilles
8 Days (7 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora IV
Departure: 29 January 2028
Visits: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Kitts and Nevis, Puerto Rico
Exclusive Savings
Suite
$5,655
From (Per Person)
A$5,655
Save 115
Per Person
Cruise
Boston To San Juan Cruise
10 Days (9 Nights) Boston to San Juan
Operator: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visits: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$1,521
Oceanview
$1,593
Balcony
$1,832
Suite
$5,759
From (Per Person)
A$1,521
Save 962
Per Person
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