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Cruises From San Juan

Choose from 146 unique cruises starting in San Juan, and travelling to Barcelona, Bridgetown, Fort Lauderdale, Lisbon, Los Angeles and more. December is the most popular month to join a cruise from San Juan and you can select from 293 departures available from twelve leading cruise lines.
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146 Cruises (293 Cruise Departures)
11 Day West Indies Explorer with Viking Cruises
Cruise
 (5)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Viking Cruises
Ship: Viking Sea
Departures: Oct 2024 to Mar 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+4 more), Barbados, Dominica, Antigua and Barbuda, Sint Maarten
Companion Fly Free
INSIDE
-
OCEANVIEW
-
BALCONY
$6,855
SUITE
$10,775
Save (per person) 1,077
From (per person) 6,855
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 09 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Aruba, Curacao
Exclusive Deal
INSIDE
$1,512
OCEANVIEW
$1,526
BALCONY
$2,016
SUITE
$3,138
Save (per person) 773
From (per person) 1,512
View Trip
11 Day San Juan, St. Vincent, Barbados & More with Virgin Voyages
Cruise
 (5)

11 Days (10 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 11 January 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+4 more), Martinique, Barbados, Saint Lucia, Saint Vincent
70% Off Second Sailor + Save
INSIDE
$2,799
OCEANVIEW
$2,901
BALCONY
$3,207
SUITE
$10,568
From (per person) 2,799
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (4)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 09 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Martinique (+4 more), Grenada, Barbados, Sint Maarten, Antigua and Barbuda
Exclusive Deal
INSIDE
$2,041
OCEANVIEW
$2,254
BALCONY
$2,863
SUITE
$3,685
From (per person) 2,041
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (4)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 11 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+3 more), Saint Vincent, Barbados, Dominica
Exclusive Deal
INSIDE
$1,944
OCEANVIEW
$2,196
BALCONY
$3,162
SUITE
$4,073
From (per person) 1,944
View Trip
14 Day Transatlantic Repositioning Cruise with Norwegian Cruise Line
Cruise
 (1)

14 Days (13 Nights) San Juan to Lisbon
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Viva
Departure: 13 April 2025
Countries Visited: Puerto Rico, Dominican Republic, Sint Maarten, Cape Verde (+2 more), Spain, Portugal
More At Sea Offer
INSIDE
$2,185
OCEANVIEW
$2,447
BALCONY
$2,645
SUITE
$4,755
From (per person) 2,185
View Trip
9 Day San Juan to St. Lucia: Holiday Edition with Virgin Voyages
Cruise
 (5)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 06 December 2024
Countries Visited: Puerto Rico, Virgin Islands, Saint Martin, Barbados (+3 more), Martinique, Saint Lucia, Saint Kitts and Nevis
70% Off Second Sailor + Save
INSIDE
$2,233
OCEANVIEW
$2,527
BALCONY
$2,741
SUITE
$13,067
From (per person) 2,233
View Trip
13 Day Amazon & Caribbean Adventure with Viking Cruises
Cruise
 (5)

13 Days (12 Nights) San Juan to Manaus
Cruise Line: Viking Cruises
Ship: Viking Sea
Departures: Nov 2024 to Feb 2025
Countries Visited: Puerto Rico, Antigua and Barbuda, Saint Lucia, Barbados (+2 more), French Guiana, Brazil
Companion Fly Free
INSIDE
-
OCEANVIEW
-
BALCONY
$8,212
SUITE
$15,283
Save (per person) 1,083
From (per person) 8,212
View Trip
8 Day Southern Caribbean with Barbados From San Juan with Princess
Cruise
 (4)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 25 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+2 more), Guadeloupe, Barbados
Exclusive Deal
INSIDE
$1,010
OCEANVIEW
$1,131
BALCONY
$1,545
SUITE
$2,059
From (per person) 1,010
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (4)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 08 February 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Saint Vincent, Barbados, Dominica, Saint Lucia, Grenada
Exclusive Deal
INSIDE
$1,908
OCEANVIEW
$2,147
BALCONY
$3,136
SUITE
$4,057
From (per person) 1,908
View Trip
8 Day Southern Caribbean with Barbados From San Juan with Princess
Cruise
 (4)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departures: Nov 2025 to Feb 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+2 more), Martinique, Barbados
Exclusive Deal
INSIDE
$1,010
OCEANVIEW
$1,120
BALCONY
$1,490
SUITE
$1,926
From (per person) 1,010
View Trip
8 Day Caribbean Yachting Hideaways with Emerald Cruises
New ReleaseCruise
 (3)

8 Days (7 Nights) San Juan to Saint John's
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 04 January 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Barthelemy, Sint Maarten (+2 more), Montserrat, Antigua and Barbuda
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
-
SUITE
$6,846
Save (per person) 4,069
From (per person) 6,846
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 15 March 2026
Countries Visited: Puerto Rico, Virgin Islands, Aruba, Curacao (+1 more), Bonaire
Exclusive DealExclusive Solo Offer
INSIDE
$1,360
OCEANVIEW
$1,434
BALCONY
$2,444
SUITE
$3,579
Save (per person) 696
From (per person) 1,360
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (4)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 12 October 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+5 more), Grenada, Barbados, Sint Maarten, Antigua and Barbuda, Saint Lucia
Exclusive Deal
INSIDE
$2,111
OCEANVIEW
$2,335
BALCONY
$3,253
SUITE
$3,725
From (per person) 2,111
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departures: Nov 2025 to Jan 2026
Countries Visited: Puerto Rico, Saint Lucia, Saint Kitts and Nevis, Antigua and Barbuda (+1 more), Virgin Islands
Exclusive DealExclusive Solo Offer
INSIDE
$1,190
OCEANVIEW
$1,354
BALCONY
$1,741
SUITE
$2,925
Save (per person) 683
From (per person) 1,190
View Trip
19 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (4)

19 Days (18 Nights) San Juan to Fort Lauderdale
Cruise Line: Princess
Ship: Grand Princess
Departure: 29 March 2026
Countries Visited: Puerto Rico, Virgin Islands, Guadeloupe, Dominica (+9 more), Grenada, Barbados, Saint Kitts and Nevis, Aruba, Curacao, Bonaire, Dominican Republic, Turks and Caicos Islands, USA
Exclusive Deal
INSIDE
$2,618
OCEANVIEW
$2,964
BALCONY
$3,835
SUITE
$4,855
From (per person) 2,618
View Trip
7 Day Western Caribbean Cruise with Royal Caribbean
Cruise
 (1)

7 Days (6 Nights) San Juan to Tampa
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 02 November 2025
Countries Visited: Puerto Rico, Dominican Republic, Jamaica, Cayman Islands (+1 more), USA
Exclusive Deal
INSIDE
$1,082
OCEANVIEW
$1,124
BALCONY
$2,105
SUITE
$2,223
Save (per person) 558
From (per person) 1,082
View Trip
10 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

10 Days (9 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 20 February 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Grenada (+2 more), Curacao, Aruba
Exclusive Deal
INSIDE
$1,589
OCEANVIEW
$1,910
BALCONY
$2,544
SUITE
$4,274
Save (per person) 797
From (per person) 1,589
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (4)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 02 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Saint Vincent, Barbados, Saint Kitts and Nevis, Martinique, Grenada
Exclusive Deal
INSIDE
$2,092
OCEANVIEW
$2,328
BALCONY
$2,983
SUITE
$3,755
From (per person) 2,092
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Nov 2024 to Mar 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Kitts and Nevis (+1 more), Barbados
Exclusive Deal
INSIDE
$1,344
OCEANVIEW
$1,420
BALCONY
$2,114
SUITE
$2,451
Save (per person) 1,631
From (per person) 1,344
View Trip
9 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

9 Days (8 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 24 May 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Dominica (+2 more), Barbados, Saint Lucia
Exclusive Deal
INSIDE
$1,422
OCEANVIEW
$1,585
BALCONY
$3,107
SUITE
$3,752
Save (per person) 689
From (per person) 1,422
View Trip
8 Day Southern Caribbean with Barbados From San Juan with Princess
Cruise
 (4)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 01 March 2026
Countries Visited: Puerto Rico, Sint Maarten, Guadeloupe, Dominica (+2 more), Grenada, Barbados
Exclusive Deal
INSIDE
$979
OCEANVIEW
$1,089
BALCONY
$1,573
SUITE
$2,048
From (per person) 979
View Trip
15 Day Southern Caribbean Adventurer From San Juan with Princess
Cruise
 (4)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 22 March 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Saint Vincent, Barbados, Guadeloupe, Dominica, Grenada
Exclusive Deal
INSIDE
$2,077
OCEANVIEW
$2,345
BALCONY
$3,195
SUITE
$3,967
From (per person) 2,077
View Trip
8 Day Resilient New Year's Ahoy with Virgin Voyages
Cruise
 (5)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 28 December 2024
Countries Visited: Puerto Rico, Virgin Islands, Barbados, Saint Lucia (+2 more), Antigua and Barbuda, Saint Martin
70% Off Second Sailor + Save
INSIDE
$2,683
OCEANVIEW
$3,179
BALCONY
$3,202
SUITE
$8,307
From (per person) 2,683
View Trip
8 Day Southern Caribbean with Barbados From San Juan with Princess
Cruise
 (4)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departures: Nov 2025 to Jan 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+2 more), Dominica, Barbados
Exclusive Deal
INSIDE
$1,010
OCEANVIEW
$1,131
BALCONY
$1,604
SUITE
$2,059
From (per person) 1,010
View Trip
8 Day Southern Caribbean with Barbados From San Juan with Princess
Cruise
 (4)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departures: Nov 2025 to Mar 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+2 more), Saint Vincent, Barbados
Exclusive Deal
INSIDE
$990
OCEANVIEW
$1,112
BALCONY
$1,545
SUITE
$1,901
From (per person) 990
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Nov 2024 to Apr 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia (+1 more), Barbados
Exclusive Deal
INSIDE
$1,393
OCEANVIEW
$1,451
BALCONY
$2,433
SUITE
$1,868
Save (per person) 3,128
From (per person) 1,393
View Trip
15 Day Discover the Yachting Islands of the Caribbean with Emerald Cruises
New ReleaseCruise
 (3)

15 Days (14 Nights) San Juan to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departure: 04 January 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Barthelemy, Sint Maarten (+3 more), Montserrat, Antigua and Barbuda, Guadeloupe
Exclusive Deal
INSIDE
-
OCEANVIEW
-
BALCONY
-
SUITE
$11,712
Save (per person) 10,118
From (per person) 11,712
View Trip
28 Day Panama Canal and Caribbean Adventurer with Princess
Cruise
 (4)

28 Days (27 Nights) San Juan to Los Angeles
Cruise Line: Princess
Ship: Grand Princess
Departure: 05 April 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Aruba (+8 more), Curacao, Bonaire, Dominican Republic, Turks and Caicos Islands, USA, Panama, Costa Rica, Mexico
Exclusive Deal
INSIDE
$4,411
OCEANVIEW
$5,173
BALCONY
$6,866
SUITE
$9,014
From (per person) 4,411
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (2)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departures: Nov 2025 to Apr 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+1 more), Saint Lucia
Exclusive DealExclusive Solo Offer
INSIDE
$1,226
OCEANVIEW
$1,294
BALCONY
$1,804
SUITE
$2,674
Save (per person) 856
From (per person) 1,226
View Trip
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