October 2026 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
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, 2026Contact cruise line for pricing & availability
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
14 Night Eastern Caribbean Cruise from Bridgetown, Barbados
14 Night Eastern Caribbean Cruise from Bridgetown, Barbados
Seabourn Seabourn Ovation
Departure Port: Bridgetown, Barbados
OCG Class
Luxury
Cruises to: RODNEY BAY, SAINT LUCIA; ST. JOHNS, ANTIGUA AND BARBUDA; CARAMBOLA BEACH, SAINT KITTS AND NEVIS; PHILIPSBURG, SINT MAARTEN; SOPERS HOLE (FRENCHMANS CAY), BVI; CARAMBOLA BEACH, SAINT KITTS AND NEVIS; TROIS ILETS, MARTINIQUE more ...
DepartingInteriorOceanviewBalconySuite
Nov 28, 2026---$6,044
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
Holland America Line Eurodam
Departure Port: Fort Lauderdale, FL
OCG Class
Premium
Cruises to: RELAXAWAY HALF MOON CAY, BAHAMAS; AMBER COVE, DOMINICAN REPUBLIC; GRAND TURK, TURKS AND CAICOS; KEY WEST, FLORIDA, US; FORT LAUDERDALE, FLORIDA, US; GRAND TURK, TURKS AND CAICOS; SAN JUAN, PUERTO RICO more ...
DepartingInteriorOceanviewBalconySuite
Nov 21, 2026$399$489$939$2,199
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
Princess Cruises Regal Princess
Departure Port: Fort Lauderdale, FL
OCG Class
Mainstream
Cruises to: AMBER COVE, DOMINICAN REPUBLIC; GRAND TURK, TURKS & CAICOS; CURACAO; ARUBA; NASSAU, BAHAMAS; FT. LAUDERDALE, FLORIDA; FT. LAUDERDALE, FLORIDA more ...
DepartingInteriorOceanviewBalconySuite
Nov 8, 2026$1,580-$1,680$2,370
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
Princess Cruises Regal Princess
Departure Port: Fort Lauderdale, FL
OCG Class
Mainstream
Cruises to: GRAND CAYMAN, CAYMAN ISLANDS; OCHO RIOS, JAMAICA; ARUBA; FT. LAUDERDALE, FLORIDA; GRAND TURK, TURKS & CAICOS; NASSAU, BAHAMAS; FT. LAUDERDALE, FLORIDA
DepartingInteriorOceanviewBalconySuite
Nov 14, 2026$1,630-$1,800$2,340
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
Princess Cruises Regal Princess
Departure Port: Fort Lauderdale, FL
OCG Class
Mainstream
Cruises to: ST. MAARTEN; SAN JUAN, PUERTO RICO; AMBER COVE, DOMINICAN REPUBLIC; GRAND TURK, TURKS & CAICOS; FT. LAUDERDALE, FLORIDA; AMBER COVE, DOMINICAN REPUBLIC; GRAND TURK, TURKS & CAICOS more ...
DepartingInteriorOceanviewBalconySuite
Nov 28, 2026$515-$855$1,395
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
Princess Cruises Regal Princess
Departure Port: Fort Lauderdale, FL
OCG Class
Mainstream
Cruises to: GRAND TURK, TURKS & CAICOS; NASSAU, BAHAMAS; FT. LAUDERDALE, FLORIDA; ST. MAARTEN; SAN JUAN, PUERTO RICO; AMBER COVE, DOMINICAN REPUBLIC; GRAND TURK, TURKS & CAICOS more ...
DepartingInteriorOceanviewBalconySuite
Nov 22, 2026$506-$866$1,286

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