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Departures
Duration
8 Days
15 Days
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Price
$800pp
$21,830pp
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108 Cruises (247 Cruise Departures)
Cruise
(5)
West Indies Explorer
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
Cruise
(4)
Southern Caribbean Adventurer From San Juan
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 15 February 2026
Countries Visited: Puerto Rico, Virgin Islands, Dominica, Saint Lucia (+5 more), Grenada, Barbados, Sint Maarten, Antigua and Barbuda, Martinique
Exclusive Deal
INSIDE
$1,908
OCEANVIEW
$2,147
BALCONY
$3,224
SUITE
$4,057
From (per person) 1,908
Cruise
(4)
Southern Caribbean Adventurer From San Juan
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 22 February 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Martinique, Barbados, Guadeloupe, Dominica, Grenada
Exclusive Deal
INSIDE
$1,939
OCEANVIEW
$2,178
BALCONY
$3,167
SUITE
$4,088
From (per person) 1,939
Cruise
(2)
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 15 March 2026
Exclusive DealExclusive Solo Offer
INSIDE
$1,360
OCEANVIEW
$1,434
BALCONY
$2,444
SUITE
$3,579
Cruise
(5)
San Juan, Barbados & Beyond
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 01 March 2025
Countries Visited: Puerto Rico, Saint Martin, Saint Lucia, Barbados (+2 more), Martinique, Saint Kitts and Nevis
70% Off Second Sailor + Save
INSIDE
$2,346
OCEANVIEW
$2,432
BALCONY
$2,687
SUITE
$8,303
From (per person) 2,346
Cruise
(4)
Southern Caribbean Adventurer From San Juan
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 30 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Dominica, Barbados, Saint Kitts and Nevis, Saint Lucia, Saint Vincent
Exclusive Deal
INSIDE
$1,943
OCEANVIEW
$2,163
BALCONY
$3,081
SUITE
$3,646
From (per person) 1,943
Cruise
(4)
Southern Caribbean Adventurer From San Juan
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 28 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Saint Vincent, Barbados, Saint Kitts and Nevis, Saint Lucia, Grenada
Exclusive Deal
INSIDE
$2,719
OCEANVIEW
$2,980
BALCONY
$3,665
SUITE
$4,507
From (per person) 2,719
Cruise
(4)
Southern Caribbean Adventurer From San Juan
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 16 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+5 more), Martinique, Barbados, Dominica, Saint Lucia, Grenada
Exclusive Deal
INSIDE
$2,195
OCEANVIEW
$2,453
BALCONY
$3,214
SUITE
$4,303
From (per person) 2,195
Cruise
(2)
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 22 March 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Antigua and Barbuda (+1 more), Barbados
Exclusive Deal
INSIDE
$1,639
OCEANVIEW
$1,790
BALCONY
$2,710
SUITE
$3,415
Cruise
(2)
Southern Caribbean Holiday
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 28 December 2025
Countries Visited: Puerto Rico, Antigua and Barbuda, Saint Lucia, Saint Kitts and Nevis (+1 more), Virgin Islands
Exclusive DealExclusive Solo Offer
INSIDE
$1,784
OCEANVIEW
$1,872
BALCONY
$2,847
SUITE
$3,587
Cruise
(4)
Southern Caribbean Adventurer From San Juan
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 07 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Saint Lucia (+5 more), Saint Vincent, Barbados, Sint Maarten, Antigua and Barbuda, Dominica
Exclusive Deal
INSIDE
$2,067
OCEANVIEW
$2,300
BALCONY
$3,156
SUITE
$3,740
From (per person) 2,067
Cruise
(2)
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 07 December 2025
Exclusive DealExclusive Solo Offer
INSIDE
$1,457
OCEANVIEW
$1,613
BALCONY
$2,131
SUITE
$3,301
Cruise
(2)
Southern Caribbean Cruise
11 Days (10 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 01 February 2026
Countries Visited: Puerto Rico, Virgin Islands, Aruba, Curacao (+3 more), Bonaire, Barbados, Saint Vincent
Exclusive Deal
INSIDE
$2,034
OCEANVIEW
$2,437
BALCONY
$3,337
SUITE
$5,020
Cruise
(4)
Southern Caribbean Adventurer From San Juan
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 01 February 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Guadeloupe (+4 more), Saint Vincent, Barbados, Sint Maarten, Antigua and Barbuda
Exclusive Deal
INSIDE
$2,042
OCEANVIEW
$2,298
BALCONY
$3,260
SUITE
$3,983
From (per person) 2,042
Cruise
(1)
Southern Caribbean Cruise
9 Days (8 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 16 May 2025
Exclusive DealExclusive Solo Offer
INSIDE
$1,248
OCEANVIEW
$1,289
BALCONY
$2,401
SUITE
$2,560
Cruise
(1)
Southern Caribbean - San Juan
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Norwegian Cruise Line
Ship: Norwegian Epic
Departures: Dec 2025 to Apr 2026
Countries Visited: Puerto Rico, Aruba, Curacao, Bonaire (+2 more), Saint Lucia, Saint Kitts and Nevis
More At Sea Offer
INSIDE
$2,495
OCEANVIEW
-
BALCONY
$3,107
SUITE
$3,413
From (per person) 2,495
Cruise
(4)
Southern Caribbean Adventurer From San Juan
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
Cruise
(1)
Southern Caribbean Cruise
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
Cruise
(2)
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 23 November 2025
Countries Visited: Puerto Rico, Virgin Islands, Curacao, Aruba
Exclusive DealExclusive Solo Offer
INSIDE
$1,566
OCEANVIEW
$1,668
BALCONY
$2,029
SUITE
$3,001
Cruise
(2)
Southern Caribbean Cruise
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
Cruise
(2)
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departures: Dec 2025 to Mar 2026
Exclusive DealExclusive Solo Offer
INSIDE
$1,407
OCEANVIEW
$1,714
BALCONY
$2,196
SUITE
$3,054
Cruise
(2)
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 04 January 2026
Exclusive DealExclusive Solo Offer
INSIDE
$1,657
OCEANVIEW
$1,704
BALCONY
$1,901
SUITE
$2,750
Cruise
(1)
Southern Caribbean Cruise
10 Days (9 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 07 March 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Sint Maarten (+2 more), Saint Lucia, Barbados
Exclusive Deal
INSIDE
$1,543
OCEANVIEW
$1,645
BALCONY
$3,468
SUITE
$5,224
Cruise
(4)
Southern Caribbean with Barbados From San Juan
8 Days (7 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 (+2 more), Grenada, Barbados
Exclusive Deal
INSIDE
$1,078
OCEANVIEW
$1,193
BALCONY
$1,494
SUITE
$1,890
From (per person) 1,078
Cruise
(4)
Southern Caribbean with Barbados From San Juan
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 19 October 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Antigua and Barbuda (+2 more), Saint Lucia, Barbados
Exclusive Deal
INSIDE
$1,200
OCEANVIEW
$1,321
BALCONY
$1,764
SUITE
$2,210
From (per person) 1,200
Cruise
(5)
San Juan, St. Vincent, Barbados & More
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
Cruise
(4)
Southern Caribbean with Barbados From San Juan
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
Cruise
(2)
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 18 January 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Grenada (+2 more), Saint Vincent, Dominica
Exclusive DealExclusive Solo Offer
INSIDE
$1,641
OCEANVIEW
$1,887
BALCONY
$2,595
SUITE
$3,417
Cruise
(4)
Southern Caribbean with Barbados From San Juan
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departures: Oct 2025 to Oct 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+2 more), Grenada, Barbados
Exclusive Deal
INSIDE
$894
OCEANVIEW
$1,009
BALCONY
$1,389
SUITE
$1,845
From (per person) 894
Cruise
(4)
Southern Caribbean Adventurer From San Juan
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 15 March 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+5 more), Grenada, Barbados, Sint Maarten, Antigua and Barbuda, Saint Vincent
Exclusive Deal
INSIDE
$2,027
OCEANVIEW
$2,290
BALCONY
$3,166
SUITE
$3,908
From (per person) 2,027
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