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Departures
Duration
7 Days
28 Days
Start City
Ship Size
Ship Features
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Price
$1,100pp
$15,830pp
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23 Cruises (24 Cruise Departures)
Cruise
(1)
Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen
10 Days (9 Nights) New York to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 29 October 2026
INSIDE
$2,096
OCEANVIEW
$2,641
BALCONY
$3,779
SUITE
$5,799
From (per person) 2,096
Cruise
(5)
One-Way San Juan Sojourn
7 Days (6 Nights) Miami to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 30 November 2024
Countries Visited: USA, Turks and Caicos Islands, Dominican Republic, Saint Kitts and Nevis (+1 more), Puerto Rico
70% Off Second Sailor + Save
INSIDE
$1,553
OCEANVIEW
$1,632
BALCONY
$1,703
SUITE
$3,647
From (per person) 1,553
Cruise
(1)
Eastern Caribbean Voyage
9 Days (8 Nights) Miami to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 31 October 2025
Countries Visited: USA, Virgin Islands, Saint Kitts and Nevis, Sint Maarten (+2 more), Saint Barthelemy, Puerto Rico
INSIDE
$1,681
OCEANVIEW
$2,116
BALCONY
$2,819
SUITE
$4,067
From (per person) 1,681
Cruise
(4)
Southern Caribbean Islander
12 Days (11 Nights) Fort Lauderdale to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 01 October 2025
Countries Visited: USA, Turks and Caicos Islands, Dominican Republic, Bonaire (+5 more), Curacao, Aruba, Saint Kitts and Nevis, Virgin Islands, Puerto Rico
Exclusive Deal
INSIDE
$1,589
OCEANVIEW
$1,722
BALCONY
$2,124
SUITE
$2,797
From (per person) 1,589
Cruise
(4)
Southern Caribbean Adventurer
19 Days (18 Nights) Fort Lauderdale to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 01 October 2025
Countries Visited: USA, Turks and Caicos Islands, Dominican Republic, Bonaire (+8 more), Curacao, Aruba, Saint Kitts and Nevis, Virgin Islands, Puerto Rico, Dominica, Grenada, Barbados
Exclusive Deal
INSIDE
$2,639
OCEANVIEW
$2,895
BALCONY
$3,698
SUITE
$4,688
From (per person) 2,639
Cruise
(2)
Boston To San Juan Cruise
8 Days (7 Nights) Boston to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 02 November 2025
Exclusive Deal
INSIDE
$1,189
OCEANVIEW
$1,401
BALCONY
$2,041
SUITE
$3,655
Cruise
(4)
Panama Canal and Caribbean Adventurer
28 Days (27 Nights) Los Angeles to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 15 September 2025
Countries Visited: USA, Mexico, Costa Rica, Panama (+8 more), Aruba, Turks and Caicos Islands, Dominican Republic, Bonaire, Curacao, Saint Kitts and Nevis, Virgin Islands, Puerto Rico
Exclusive Deal
INSIDE
$4,341
OCEANVIEW
$4,781
BALCONY
$5,952
SUITE
$8,281
From (per person) 4,341
Cruise
Ft. Lauderdale To San Juan
9 Days (8 Nights) Fort Lauderdale to San Juan
Cruise Line: Royal Caribbean
Ship: Jewel of the Seas
Departure: 31 October 2025
Countries Visited: USA, Haiti, Saint Kitts and Nevis, Saint Lucia (+3 more), Dominica, Sint Maarten, Puerto Rico
Exclusive Deal
INSIDE
$1,127
OCEANVIEW
$1,155
BALCONY
$1,495
SUITE
$3,040
Cruise
A Journey From Chic French Beaches to Rain-forested Peaks
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 14 January 2025
Countries Visited: USA, Virgin Islands, Saint Barthelemy, Guadeloupe (+2 more), Saint Martin, Puerto Rico
Anniversary Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$6,583
SUITE
$7,672
From (per person) 5,925
Cruise
A Journey from Miami to San Juan
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 22 December 2025
Anniversary Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$8,019
SUITE
$9,603
From (per person) 7,217
Cruise
One-way to SJ: DR, St. Maarten & BVI
7 Days (6 Nights) Miami to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 02 November 2025
70% Off Second Sailor + Save
INSIDE
$1,738
OCEANVIEW
$1,982
BALCONY
$2,166
SUITE
$4,726
From (per person) 1,738
Cruise
New Year In The Tropics
12 Days (11 Nights) Miami to San Juan
Cruise Line: Regent Seven Seas
Ship: Seven Seas Navigator
Departure: 23 December 2024
Countries Visited: USA, Jamaica, Aruba, Curacao (+4 more), Bonaire, Virgin Islands, Sint Maarten, Puerto Rico
Exclusive Deal
INSIDE
-
OCEANVIEW
$9,248
BALCONY
$11,832
SUITE
$13,317
Cruise
An Extended Journey From Caribbean Rhythms To Jungle Mysteries
15 Days (14 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 07 January 2025
Countries Visited: USA, Jamaica, Cayman Islands, Mexico (+5 more), Virgin Islands, Saint Barthelemy, Guadeloupe, Saint Martin, Puerto Rico
Anniversary Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$9,652
SUITE
$11,217
From (per person) 9,652
New ReleaseCruise
Caribbean escapade
8 Days (7 Nights) Miami to San Juan
Cruise Line: Emerald Cruises
Ship: Emerald Sakara
Departure: 30 November 2026
Countries Visited: USA, Bahamas, Turks and Caicos Islands, Puerto Rico
Exclusive Deal
INSIDE
-
OCEANVIEW
$5,440
BALCONY
-
SUITE
$6,979
Cruise
A Journey to Butterfly Isles & French Caribbean Chic
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 20 December 2024
Anniversary Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$8,019
SUITE
$9,603
From (per person) 7,618
Cruise
An Extended Journey From Mayan Mysteries To Castaway Chic
15 Days (14 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 14 February 2025
Countries Visited: USA, Mexico, Belize, Virgin Islands (+4 more), Anguilla, Guadeloupe, Saint Martin, Puerto Rico
Anniversary Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$8,999
SUITE
$10,850
From (per person) 8,999
Cruise
A Journey From Miami To San Juan
9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 12 November 2025
Countries Visited: USA, Virgin Islands, Guadeloupe, Barbados (+3 more), Dominica, Saint Martin, Puerto Rico
Anniversary Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$7,177
SUITE
$8,266
From (per person) 5,381
Cruise
A Journey of Paradise Coves and Puerto Rican Spirits
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 24 February 2026
Countries Visited: USA, Virgin Islands, Antigua and Barbuda, Saint Barthelemy (+1 more), Puerto Rico
Anniversary Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$6,286
SUITE
$7,524
From (per person) 5,658
Cruise
A Journey From Miami To San Juan
9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 13 January 2026
Countries Visited: USA, Virgin Islands, Guadeloupe, Grenada (+3 more), Barbados, Montserrat, Puerto Rico
Anniversary Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$7,177
SUITE
$8,266
From (per person) 5,742
Cruise
An Extended Journey Of Central American Jungles And Caribbean Isles
18 Days (17 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departure: 04 February 2025
Countries Visited: USA, Cayman Islands, Mexico, Anguilla (+4 more), Dominica, Guadeloupe, Saint Martin, Puerto Rico
Anniversary Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$12,672
SUITE
$15,008
From (per person) 12,672
Cruise
A Journey Of Calypso Rhythms And Coconut Breezes
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora II
Departures: Nov 2024 to Feb 2025
Anniversary Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$6,880
SUITE
$8,217
From (per person) 5,504
Cruise
A Journey From Miami To San Juan
9 Days (8 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 29 December 2025
Countries Visited: USA, Virgin Islands, Guadeloupe, Barbados (+3 more), Martinique, Saint Kitts and Nevis, Puerto Rico
Anniversary Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$9,801
SUITE
$11,781
From (per person) 8,331
Cruise
A Journey to Boho-chic Beaches on Rum-Casked Islands
8 Days (7 Nights) Miami to San Juan
Cruise Line: Explora Journeys
Ship: Explora I
Departure: 21 February 2025
Anniversary Offer
INSIDE
-
OCEANVIEW
-
BALCONY
$6,286
SUITE
$7,524
From (per person) 5,341
Results: 23 results
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