Filter Results
55 Cruises (63 Departures)
55 Cruises (63 Departures)
Departures
Duration
4 Days
18 Days
Start City
Ship Size
Ship Features
Operators
Price
$600pp
$54,825pp
Countries
Cruise
(6)
Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen
10 Days (9 Nights) New York to San Juan
Operator: Azamara
Ship: Azamara Quest
Departure: 28 October 2027
Visits: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Exclusive Savings
Inside
$2,805
Oceanview
$3,246
Balcony
$3,981
Suite
$6,813
From (Per Person)
A$2,805
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
$1,938
Oceanview
$2,459
Balcony
$2,710
Suite
$5,037
From (Per Person)
A$1,938
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
$6,282
From (Per Person)
A$6,282
Save 128
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
$3,028
Oceanview
$3,282
Balcony
$4,026
Suite
$5,142
From (Per Person)
A$3,028
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
$739
Oceanview
$657
Balcony
$749
Suite
$1,607
From (Per Person)
A$657
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
$894
Oceanview
$1,033
Balcony
$1,251
Suite
$2,280
From (Per Person)
A$894
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
$1,711
Oceanview
$1,711
Balcony
$2,445
Suite
$3,033
From (Per Person)
A$1,711
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
$5,968
From (Per Person)
A$5,968
Save 122
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
$8,369
From (Per Person)
A$8,369
Save 171
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
$5,968
From (Per Person)
A$5,968
Save 122
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
$5,968
From (Per Person)
A$5,968
Save 122
Per Person
Cruise
A Journey Of Sunny Shores & Caribbean Island Bliss
9 Days (8 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora III
Departure: 21 January 2027
Visits: USA, Virgin Islands, Anguilla, Martinique, Saint Kitts and Nevis, Saint Martin, Puerto Rico
Exclusive Savings
Suite
$9,290
From (Per Person)
A$9,290
Save 190
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
$14,073
From (Per Person)
A$14,073
Save 287
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
Balcony
$7,299
Suite
$10,254
From (Per Person)
A$5,398
Save 3,597
Per Person
Cruise
A Journey Of Tropical Festivities & Dazzling Island Beauty
9 Days (8 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora III
Departure: 20 December 2026
Visits: USA, Jamaica, Dominican Republic, Virgin Islands, Saint Martin, Puerto Rico
Exclusive Savings
Suite
$33,589
From (Per Person)
A$33,589
Save 686
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
$5,251
Balcony
$6,655
Suite
$7,006
From (Per Person)
A$5,251
Save 649
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
$10,741
From (Per Person)
A$10,741
Save 219
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
$1,661
Oceanview
$1,734
Balcony
$2,078
Suite
$6,287
From (Per Person)
A$1,661
Save 822
Per Person
Cruise
An Extended Journey of Island Energy & Ocean Tranquillity
17 Days (16 Nights) San Juan to San Juan
Operator: Explora Journeys
Ship: Explora III
Departure: 13 January 2027
Visits: Puerto Rico, Saint Martin, Guadeloupe, Grenada +7 more, Saint Lucia, Dominican Republic, USA, Virgin Islands, Anguilla, Martinique, Saint Kitts and Nevis
Exclusive Savings
Suite
$17,287
From (Per Person)
A$17,287
Save 353
Per Person
Cruise
An Extended Journey of Pearl-Blue Horizons & Maritime Grace
17 Days (16 Nights) Miami to San Juan
Operator: Explora Journeys
Ship: Explora III
Departure: 19 February 2027
Visits: USA, Dominican Republic, Puerto Rico, Virgin Islands, Anguilla, Antigua and Barbuda, Guadeloupe
Exclusive Savings
Suite
$13,818
From (Per Person)
A$13,818
Save 282
Per Person
Cruise
Miami to San Juan
11 Days (10 Nights) Miami to San Juan
Operator: Silversea
Ship: Silver Shadow
Departure: 10 December 2026
Visits: USA, Virgin Islands, Saint Martin, Saint Kitts and Nevis +4 more, Guadeloupe, Martinique, Montserrat, Puerto Rico
Exclusive Savings
Oceanview
$6,762
Balcony
$7,448
Suite
$11,368
From (Per Person)
A$6,762
Save 1,888
Per Person
New ReleaseCruise
Fort Lauderdale to San Juan
5 Days (4 Nights) Fort Lauderdale to San Juan
Operator: Crystal
Ship: Crystal Serenity
Departure: 23 November 2026
Visits: USA, Bahamas, Dominican Republic, Puerto Rico
Exclusive Savings
Oceanview
$3,617
Balcony
$4,105
Suite
$4,105
From (Per Person)
A$3,617
Save 83
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
$7,164
From (Per Person)
A$7,164
Save 146
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
$19,992
From (Per Person)
A$19,992
Save 408
Per Person
New ReleaseCruise
Fort Lauderdale to San Juan
9 Days (8 Nights) Fort Lauderdale to San Juan
Operator: Crystal
Ship: Crystal Grace
Departures: Jan 2029
Visits: USA, Turks and Caicos Islands, Dominican Republic, Virgin Islands +4 more, Antigua and Barbuda, Saint Kitts and Nevis, Saint Barthelemy, Puerto Rico
Exclusive Savings
Balcony
$7,106
Suite
$7,281
From (Per Person)
A$7,106
Save 956
Per Person
Cruise
A Journey Of Caribbean Adventure & Shimmering Tropical Harmony
8 Days (7 Nights) Miami to San Juan
Operator: Explora Journeys
Departures: Nov 2026 to Dec 2026
Visits: USA, Virgin Islands, Antigua and Barbuda, Guadeloupe, Saint Martin, Puerto Rico
Exclusive Savings
Suite
$6,541
From (Per Person)
A$6,541
Save 140
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
$19,404
From (Per Person)
A$19,404
Save 396
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
$1,177
Oceanview
$1,246
Balcony
$2,309
Suite
$3,053
From (Per Person)
A$1,177
Save 670
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
$15,802
From (Per Person)
A$15,802
Save 323
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
$53,728
From (Per Person)
A$53,728
Save 1,097
Per Person
No trips found. Try adjusting the search filters.
