Filter Results
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
(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
$5,514
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
$1,211
Oceanview
$1,231
Balcony
$1,439
Suite
$2,399
From (Per Person)
A$1,211
Per Person
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
$8,078
Oceanview
$9,447
Balcony
$11,653
Suite
$18,421
From (Per Person)
A$8,078
Save 541
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
$2,465
Oceanview
$2,894
Balcony
$3,257
Suite
$5,237
From (Per Person)
A$2,465
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
(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
$2,573
Oceanview
$2,983
Balcony
$3,634
Suite
$6,204
From (Per Person)
A$2,573
Save 166
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
$935
Oceanview
$980
Balcony
$1,025
Suite
$1,100
From (Per Person)
A$935
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 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
(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
(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
$1,109
Oceanview
$1,178
Balcony
$1,762
Suite
$2,287
From (Per Person)
A$1,109
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)
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
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
$1,555
Oceanview
$1,628
Balcony
$1,867
Suite
$5,829
From (Per Person)
A$1,555
Save 928
Per Person
Cruise
An Extended Journey Into Island Delights, Hidden Coves & Chic Coastlines
15 Days (14 Nights) San Juan to San Juan
Operator: 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
Suite
$15,053
From (Per Person)
A$15,053
Save 307
Per Person
Cruise
An Extended Journey Of Cultural Treasures & Seaside Harmony
16 Days (15 Nights) Miami to San Juan
Operator: 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
Suite
$11,613
From (Per Person)
A$11,613
Save 237
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 163
Per Person
Cruise
Baltimore To San Juan Cruise
9 Days (8 Nights) Baltimore to San Juan
Operator: Royal Caribbean
Ship: Vision of the Seas
Departure: 21 October 2027
Visits: USA, Turks and Caicos Islands, Aruba, Curacao, Puerto Rico
Exclusive Savings
Inside
$1,126
Oceanview
$1,278
Balcony
$2,240
Suite
$3,115
From (Per Person)
A$1,126
Save 665
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
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
A Journey Through Island Charm & Cultural Treasures
8 Days (7 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora IV
Departures: Mar 2028 to Apr 2028
Visits: USA, Turks and Caicos Islands, Saint Barthelemy, Antigua and Barbuda, Anguilla, Puerto Rico
Exclusive Savings
Suite
$5,277
From (Per Person)
A$5,277
Save 115
Per Person
New ReleaseCruise
Caribbean escapade
8 Days (7 Nights) Miami to San Juan
Operator: Emerald Cruises
Ship: Emerald Sakara
Departure: 30 November 2026
Visits: USA, Bahamas, Turks and Caicos Islands, Puerto Rico
Exclusive Savings
Oceanview
$5,398
Suite
$6,922
From (Per Person)
A$5,398
Save 3,597
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
$14,104
Suite
$14,242
From (Per Person)
A$14,104
Save 2,256
Per Person
Cruise
An Extended Journey of Tropical Harmony & Natural Wonders
15 Days (14 Nights) San Juan to San Juan
Operator: 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
Suite
$13,230
From (Per Person)
A$13,230
Save 270
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
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
A Journey From Glorious Shorelines To Nature's Allure
8 Days (7 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora III
Departure: 29 March 2027
Visits: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Puerto Rico
Exclusive Savings
Suite
$6,757
From (Per Person)
A$6,757
Save 138
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
New ReleaseCruise
Fort Lauderdale to San Juan
11 Days (10 Nights) Fort Lauderdale to San Juan
Operator: Crystal
Ship: Crystal Symphony
Departure: 03 December 2026
Visits: USA, Virgin Islands, Saint Barthelemy, Guadeloupe +5 more, Saint Vincent, Saint Lucia, Martinique, Saint Kitts and Nevis, Puerto Rico
Exclusive Savings
Oceanview
$6,362
Balcony
$7,825
Suite
$8,215
From (Per Person)
A$6,362
Save 1,638
Per Person
Cruise
A Journey Of Tranquil Tropical Beauty & Rainforest Adventures
9 Days (8 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora III
Departure: 05 January 2027
Visits: USA, Virgin Islands, Saint Barthelemy, Antigua and Barbuda, Saint Kitts and Nevis, Puerto Rico
Exclusive Savings
Suite
$8,820
From (Per Person)
A$8,820
Save 180
Per Person
No trips found. Try adjusting the search filters.
