October 2026 All Caribbean Cruises

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14 Night Caribbean Cruise from La Romana, Dominican Republic
14 Night Caribbean Cruise from La Romana, Dominican Republic
MSC Cruises MSC Opera
Departure Port: La Romana, Dominican Republic
OCG Class
Mainstream
Cruises to: Catalina Island Dominican Republic; Bridgetown Barbados; Fort De France Martinique; Pointe-a-pitre Guadeloupe; Road Town British Virgin Islands; La Romana Dominican Republic; Samana Bay Dominican Republic more ...
DepartingInteriorOceanviewBalconySuite
Nov 16, 2026$920$1,220$2,030$3,320
14 Night Caribbean Cruise from Miami, FL
14 Night Caribbean Cruise from Miami, FL
Holland America Line Zuiderdam
Departure Port: Miami, FL
OCG Class
Premium
Cruises to: KEY WEST, FLORIDA, US; OCHO RIOS, JAMAICA; GEORGETOWN, CAYMAN ISLANDS; COZUMEL, MEXICO; MIAMI, FLORIDA, US; RELAXAWAY HALF MOON CAY, BAHAMAS; AMBER COVE, DOMINICAN REPUBLIC more ...
DepartingInteriorOceanviewBalconySuite
Nov 21, 2026$539$629$899$1,749
14 Night Caribbean Cruise from Port Canaveral, FL
14 Night Caribbean Cruise from Port Canaveral, FL
Carnival Cruise Line Carnival Venezia
Departure Port: Port Canaveral, FL
OCG Class
Mainstream
Cruises to: St. Thomas, Usvi (dock); Antigua (dock); Martinique, Fwi (dock); Barbados (dock); St. Maarten, Na (dock); San Juan, Puerto Rico (dock); Port Canaveral (orlando), Fl (dock)
DepartingInteriorOceanviewBalconySuite
Oct 18, 2026$639---
14 Night Caribbean Cruise from Port Canaveral, FL
14 Night Caribbean Cruise from Port Canaveral, FL
Carnival Cruise Line Carnival Venezia
Departure Port: Port Canaveral, FL
OCG Class
Mainstream
Cruises to: St. Thomas, Usvi (dock); Antigua (dock); Dominica (dock); Barbados (dock); St. Maarten, Na (dock); St. Kitts, Wi (dock); San Juan, Puerto Rico (dock) more ...
DepartingInteriorOceanviewBalconySuite
Nov 29, 2026$515--$5,679
14 Night Caribbean Cruise from Port Canaveral, FL
14 Night Caribbean Cruise from Port Canaveral, FL
Princess Cruises Caribbean Princess
Departure Port: Port Canaveral, FL
OCG Class
Mainstream
Cruises to: San Juan de Puerto Rico; Amber Cove; Grand Turk; Puerto Cañaveral; Nassau; Princess Cays; Amber Cove more ...
DepartingInteriorOceanviewBalconySuite
Oct 4, 2026Contact 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, ST. KITTS; GUSTAVIA, ST. BARTHELEMY; PHILIPSBURG, ST. MAARTEN; SAN JUAN; SAN JUAN; ST. GEORGE'S, GRENADA; BEQUIA more ...
DepartingInteriorOceanviewBalconySuite
Nov 15, 2026-$5,280$6,456$8,612
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: ST. GEORGE'S, GRENADA; BEQUIA; MARIGOT BAY; SAN JUAN; SAN JUAN; BASSETERRE, ST. KITTS; GUSTAVIA, ST. BARTHELEMY more ...
DepartingInteriorOceanviewBalconySuite
Nov 8, 2026-$3,286$5,196$6,624
14 Night Caribbean Cruise from Southampton, England
14 Night Caribbean Cruise from Southampton, England
P&O Cruises Arvia
Departure Port: Southampton, England
OCG Class
Mainstream
Cruises to: TENERIFE, SPAIN; ST MAARTEN, SAINT MAARTEN; BASSETERRE, SAINT KITTS AND NEVIS; CASTRIES, SAINT LUCIA; BRIDGETOWN, BARBADOS
DepartingInteriorOceanviewBalconySuite
Oct 23, 2026Contact cruise line for pricing & availability
14 Night Caribbean Cruise from Southampton, England
14 Night Caribbean Cruise from Southampton, England
P&O Cruises Britannia
Departure Port: Southampton, England
OCG Class
Mainstream
Cruises to: TENERIFE, SPAIN; ST MAARTEN, SAINT MAARTEN; DOMINICA, DOMINICA; CASTRIES, SAINT LUCIA; BRIDGETOWN, BARBADOS
DepartingInteriorOceanviewBalconySuite
Oct 30, 2026Contact cruise line for pricing & availability
14 Night Caribbean Cruise from St John's, Antigua, Antigua and Barbuda
14 Night Caribbean Cruise from St John's, Antigua, Antigua and Barbuda
P&O Cruises Arvia
Departure Port: St John's, Antigua, Antigua and Barbuda
OCG Class
Mainstream
Cruises to: ANTIGUA, ANTIGUA AND BARBUDA; CASTRIES, SAINT LUCIA; BRIDGETOWN, BARBADOS; BRIDGETOWN, BARBADOS; FORT DE FRANCE, MARTINIQUE; BASSETERRE, SAINT KITTS AND NEVIS; ST MAARTEN, SAINT MAARTEN more ...
DepartingInteriorOceanviewBalconySuite
Nov 14, 2026Contact cruise line for pricing & availability
Nov 28, 2026Contact cruise line for pricing & availability