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Departures
Duration
7 Days
28 Days
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$800pp
$22,530pp
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191 Cruises (424 Cruise Departures)
New ReleaseCruise
(3)
Caribbean Yachting Hideaways
8 Days (7 Nights) San Juan to Saint John's
Cruise Line: Emerald Cruises
Ship: Emerald Azzurra
Departures: Dec 2025 to Feb 2026
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Barthelemy (+2 more), Montserrat, Antigua and Barbuda
Super Earlybird
INSIDE
-
OCEANVIEW
$6,440
BALCONY
-
SUITE
$8,192
Cruise
(5)
West Indies Explorer
11 Days (10 Nights) San Juan to San Juan
Operated By: Viking Cruises
Ship: Viking Sea
Departures: Dec 2025 to Feb 2027
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
$6,561
SUITE
$9,991
Cruise
(2)
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departures: Feb 2027 to Apr 2027
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+2 more), Grenada, Saint Vincent
Exclusive Deal
INSIDE
$1,179
OCEANVIEW
$1,285
BALCONY
$1,734
SUITE
$3,134
Cruise
(5)
Southern Caribbean Adventurer
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 26 October 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+4 more), Grenada, Barbados, Antigua and Barbuda, Saint Martin
Exclusive Deal
INSIDE
$2,383
OCEANVIEW
$2,645
BALCONY
$3,472
SUITE
$4,264
From (per person) 2,383
Cruise
(2)
Southern Caribbean Cruise
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 Deal
INSIDE
$1,029
OCEANVIEW
$1,215
BALCONY
$1,451
SUITE
$2,883
Cruise
(1)
Eastern Caribbean Voyage
19 Days (18 Nights) San Juan to Miami
Cruise Line: Azamara Cruises
Ship: Azamara Quest
Departure: 19 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+8 more), Saint Vincent, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin, USA
INSIDE
$6,135
OCEANVIEW
$6,640
BALCONY
$7,323
SUITE
$10,551
From (per person) 6,135
Cruise
(5)
Southern Caribbean with Barbados and Antigua
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 01 March 2026
Countries Visited: Puerto Rico, Saint Martin, Antigua and Barbuda, Dominica (+2 more), Grenada, Barbados
Exclusive Deal
INSIDE
$993
OCEANVIEW
$1,141
BALCONY
$1,647
SUITE
$1,963
From (per person) 993
Cruise
(5)
Southern Caribbean Adventurer
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, Saint Martin, Antigua and Barbuda (+5 more), Saint Vincent, Barbados, Saint Kitts and Nevis, Saint Lucia, Grenada
Exclusive Deal
INSIDE
$3,670
OCEANVIEW
$4,138
BALCONY
$4,571
SUITE
$5,254
From (per person) 3,670
Cruise
(5)
Southern Caribbean Adventurer
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, Saint Martin, Antigua and Barbuda (+5 more), Saint Kitts and Nevis, Saint Lucia, Dominica, Grenada, Barbados
Exclusive Deal
INSIDE
$2,324
OCEANVIEW
$2,627
BALCONY
$3,591
SUITE
$4,561
From (per person) 2,324
Cruise
(2)
Southern Caribbean Holiday
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 27 December 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica (+1 more), Saint Martin
Exclusive Deal
INSIDE
$1,628
OCEANVIEW
$1,851
BALCONY
$2,346
SUITE
$3,597
Cruise
(5)
Southern Caribbean with Barbados and Antigua Holiday
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 21 December 2025
Exclusive Deal
INSIDE
$1,557
OCEANVIEW
$1,771
BALCONY
$2,349
SUITE
$2,617
From (per person) 1,557
Cruise
(1)
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 30 March 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Kitts and Nevis (+1 more), Barbados
Exclusive Deal
INSIDE
$2,141
OCEANVIEW
-
BALCONY
-
SUITE
$5,468
Cruise
(1)
Caribbean Cruise: San Juan, Antigua & Barbados
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 21 November 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Martinique (+9 more), Saint Vincent, Grenada, Trinidad and Tobago, Barbados, Saint Lucia, Dominica, Saint Kitts and Nevis, Saint Martin, Saint Barthelemy
INSIDE
$3,676
OCEANVIEW
$4,508
BALCONY
$6,003
SUITE
$9,913
From (per person) 3,676
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 Deal
INSIDE
$1,441
OCEANVIEW
$1,659
BALCONY
$1,899
SUITE
$3,367
Cruise
(1)
Southern Caribbean Cruise
9 Days (8 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departure: 13 April 2025
Countries Visited: Puerto Rico, Virgin Islands, Sint Maarten, Saint Kitts and Nevis (+2 more), Barbados, Dominica
Exclusive Deal
INSIDE
$2,286
OCEANVIEW
-
BALCONY
$3,414
SUITE
$4,858
Cruise
(1)
Southern Caribbean Cruise: Antigua, St. Barts & Martinique
11 Days (10 Nights) San Juan to Bridgetown
Cruise Line: Azamara Cruises
Ship: Azamara Journey
Departure: 18 December 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Barthelemy (+4 more), Martinique, Saint Vincent, Trinidad and Tobago, Barbados
INSIDE
$2,709
OCEANVIEW
$3,313
BALCONY
$4,462
SUITE
$7,333
From (per person) 2,709
Cruise
(5)
Southern Caribbean Adventurer
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, Saint Martin, Antigua and Barbuda (+2 more), Dominica, Barbados
Exclusive Deal
INSIDE
$1,839
OCEANVIEW
$2,125
BALCONY
$3,423
SUITE
$4,146
From (per person) 1,839
Cruise
(2)
Southern Caribbean Cruise
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 01 March 2026
Countries Visited: Puerto Rico, Curacao, Aruba, Virgin Islands
Exclusive Deal
INSIDE
$1,059
OCEANVIEW
$1,138
BALCONY
$1,349
SUITE
$2,663
Cruise
(5)
Southern Caribbean with Barbados and Antigua
From (per person) 964
Cruise
(5)
Southern Caribbean Adventurer
19 Days (18 Nights) San Juan to Fort Lauderdale
Cruise Line: Princess
Ship: Grand Princess
Departure: 29 March 2026
Countries Visited: Puerto Rico, Saint Martin, Dominica, Grenada (+9 more), Barbados, Virgin Islands, Saint Kitts and Nevis, Aruba, Curacao, Bonaire, Dominican Republic, Turks and Caicos Islands, USA
Exclusive Deal
INSIDE
$2,643
OCEANVIEW
$2,898
BALCONY
$4,068
SUITE
$4,860
From (per person) 2,643
Cruise
(2)
Southern Caribbean Cruise
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
$1,291
OCEANVIEW
$1,339
BALCONY
$1,620
SUITE
$3,147
Cruise
(5)
Puerto Rican Daze & Caribbean Nights
11 Days (10 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Resilient Lady
Departure: 22 March 2025
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Saint Kitts and Nevis (+4 more), Martinique, Saint Lucia, Barbados, Saint Vincent
Up To USD $300 Bar Tab
INSIDE
-
OCEANVIEW
-
BALCONY
$3,901
SUITE
$7,799
From (per person) 3,901
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
INSIDE
$2,391
OCEANVIEW
-
BALCONY
-
SUITE
-
From (per person) 2,391
Cruise
(3)
Southern Caribbean with Barbados and St. Kitts
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Crown Princess
Departures: Jan 2027 to Feb 2027
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Dominica (+2 more), Grenada, Barbados
Exclusive Deal
INSIDE
$1,171
OCEANVIEW
$1,327
BALCONY
$1,785
SUITE
$2,221
From (per person) 1,171
Cruise
(5)
Southern Caribbean Adventurer
15 Days (14 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 23 November 2025
Countries Visited: Puerto Rico, Saint Martin, Saint Lucia, Barbados (+4 more), Grenada, Dominica, Virgin Islands, Antigua and Barbuda
Exclusive Deal
INSIDE
$2,581
OCEANVIEW
$2,916
BALCONY
$3,571
SUITE
$4,462
From (per person) 2,581
Cruise
(5)
Southern Caribbean Islander
12 Days (11 Nights) San Juan to Fort Lauderdale
Cruise Line: Princess
Ship: Grand Princess
Departure: 05 April 2026
Countries Visited: Puerto Rico, Virgin Islands, Saint Kitts and Nevis, Aruba (+5 more), Curacao, Bonaire, Dominican Republic, Turks and Caicos Islands, USA
Exclusive Deal
INSIDE
$1,491
OCEANVIEW
$1,578
BALCONY
$2,382
SUITE
$2,679
From (per person) 1,491
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 Deal
INSIDE
$1,968
OCEANVIEW
$2,332
BALCONY
$2,538
SUITE
$5,417
Cruise
(5)
Southern Caribbean with Barbados and Antigua
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 29 March 2026
Exclusive Deal
INSIDE
$1,092
OCEANVIEW
$1,269
BALCONY
$1,646
SUITE
$2,122
From (per person) 1,092
Cruise
(2)
Southern Caribbean Holiday
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Brilliance of the Seas
Departure: 20 December 2026
Countries Visited: Puerto Rico, Virgin Islands, Antigua and Barbuda, Dominica (+1 more), Saint Kitts and Nevis
Exclusive DealExclusive Solo Offer
INSIDE
$1,564
OCEANVIEW
$1,787
BALCONY
$2,171
SUITE
$3,559
Cruise
(5)
Southern Caribbean with Barbados and Antigua Holiday
8 Days (7 Nights) San Juan to San Juan
Cruise Line: Princess
Ship: Grand Princess
Departure: 28 December 2025
Countries Visited: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda (+2 more), Saint Vincent, Barbados
Exclusive Deal
INSIDE
-
OCEANVIEW
$2,777
BALCONY
$2,874
SUITE
$3,112
From (per person) 2,777
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