October 2025 All Caribbean Cruises

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14 Night Caribbean Cruise from San Juan, Puerto Rico
14 Night Caribbean Cruise from San Juan, Puerto Rico
Azamara Azamara Quest
Departure Port: San Juan, Puerto Rico
OCG Class
Premium
Cruises to: ST. JOHN'S, ANTIGUA; SAINT GEORGE'S; SCARBOROUGH, TOBAGO; BRIDGETOWN; BRIDGETOWN; CASTRIES; ROSEAU more ...
DepartingInteriorOceanviewBalconySuite
Nov 8, 2025$2,680$3,280$4,980$6,150
Nov 22, 2025$2,320$2,650$3,490$4,810
14 Night Caribbean Cruise from San Juan, Puerto Rico
14 Night Caribbean Cruise from San Juan, Puerto Rico
Princess Cruises Grand Princess
Departure Port: San Juan, Puerto Rico
OCG Class
Mainstream
Cruises to: Tortola; Dominica; Barbados; San Juan de Puerto Rico; St. Thomas; St. Maarten; Antigua more ...
DepartingInteriorOceanviewBalconySuite
Oct 12, 2025Contact cruise line for pricing & availability
14 Night Caribbean Cruise from San Juan, Puerto Rico
14 Night Caribbean Cruise from San Juan, Puerto Rico
Princess Cruises Grand Princess
Departure Port: San Juan, Puerto Rico
OCG Class
Mainstream
Cruises to: St. Thomas; St. Maarten; Antigua; St. Lucia; Barbados; San Juan de Puerto Rico; Tortola more ...
DepartingInteriorOceanviewBalconySuite
Oct 19, 2025Contact cruise line for pricing & availability
14 Night Caribbean Cruise from San Juan, Puerto Rico
14 Night Caribbean Cruise from San Juan, Puerto Rico
Princess Cruises Grand Princess
Departure Port: San Juan, Puerto Rico
OCG Class
Mainstream
Cruises to: St. Thomas; St. Maarten; Antigua; Barbados; San Juan de Puerto Rico; Martinica; Barbados more ...
DepartingInteriorOceanviewBalconySuite
Nov 2, 2025Contact cruise line for pricing & availability
14 Night Caribbean Cruise from San Juan, Puerto Rico
14 Night Caribbean Cruise from San Juan, Puerto Rico
Princess Cruises Grand Princess
Departure Port: San Juan, Puerto Rico
OCG Class
Mainstream
Cruises to: Tortola; Dominica; Point-A-Pitre; Barbados; San Juan de Puerto Rico; St. Thomas; St. Maarten more ...
DepartingInteriorOceanviewBalconySuite
Oct 26, 2025Contact cruise line for pricing & availability
14 Night Caribbean Cruise from San Juan, Puerto Rico
14 Night Caribbean Cruise from San Juan, Puerto Rico
Princess Cruises Grand Princess
Departure Port: San Juan, Puerto Rico
OCG Class
Mainstream
Cruises to: Martinica; Barbados; San Juan de Puerto Rico; St. Thomas; St. Maarten; Antigua; Martinica more ...
DepartingInteriorOceanviewBalconySuite
Nov 9, 2025Contact cruise line for pricing & availability
14 Night Caribbean Cruise from San Juan, Puerto Rico
14 Night Caribbean Cruise from San Juan, Puerto Rico
Princess Cruises Grand Princess
Departure Port: San Juan, Puerto Rico
OCG Class
Mainstream
Cruises to: St. Thomas; St. Maarten; Antigua; Dominica; Barbados; San Juan de Puerto Rico; St. Lucia more ...
DepartingInteriorOceanviewBalconySuite
Nov 30, 2025Contact cruise line for pricing & availability
14 Night Caribbean Cruise from San Juan, Puerto Rico
14 Night Caribbean Cruise from San Juan, Puerto Rico
Princess Cruises Grand Princess
Departure Port: San Juan, Puerto Rico
OCG Class
Mainstream
Cruises to: St. Thomas; St. Maarten; Antigua; Martinica; Barbados; San Juan de Puerto Rico; Dominica more ...
DepartingInteriorOceanviewBalconySuite
Nov 16, 2025Contact cruise line for pricing & availability
14 Night Caribbean Cruise from San Juan, Puerto Rico
14 Night Caribbean Cruise from San Juan, Puerto Rico
Princess Cruises Grand Princess
Departure Port: San Juan, Puerto Rico
OCG Class
Mainstream
Cruises to: Dominica; St. Lucia; Barbados; San Juan de Puerto Rico; St. Thomas; St. Maarten; Antigua more ...
DepartingInteriorOceanviewBalconySuite
Nov 23, 2025Contact cruise line for pricing & availability
14 Night Caribbean Cruise from San Juan, Puerto Rico
14 Night Caribbean Cruise from San Juan, Puerto Rico
Windstar Cruises Star Pride
Departure Port: San Juan, Puerto Rico
OCG Class
Luxury
Cruises to: Basseterre; Gustavia; Philipsburg, St. Maarten; San Juan; St. George's; Bequia; Marigot, St. Martin more ...
DepartingInteriorOceanviewBalconySuite
Nov 2, 2025-$4,599$7,099$9,499
Nov 16, 2025-$4,099$6,514$8,999

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