October 2025 All Caribbean Cruises

New Search for Cruises

Filter and Sort Reset Filters

Showing 441 - 450 of 536 Cruises
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; Bequia; Marigot, St. Martin; San Juan; Basseterre; Gustavia; Philipsburg, St. Maarten more ...
DepartingInteriorOceanviewBalconySuite
Nov 9, 2025-$4,099$6,514$8,999
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; Bequia; Marigot, St. Martin; San Juan; Gustavia; Basseterre; Philipsburg, St. Maarten more ...
DepartingInteriorOceanviewBalconySuite
Nov 23, 2025-$4,099$6,514$8,999
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 24, 2025Contact 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 31, 2025Contact 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 15, 2025Contact 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; BASSETERRE, SAINT KITTS AND NEVIS; TORTOLA, VIRGIN ISLANDS, BRITISH; ST MAARTEN, SAINT MAARTEN more ...
DepartingInteriorOceanviewBalconySuite
Nov 29, 2025Contact cruise line for pricing & availability
14 Night Eastern Caribbean Cruise from Boston, MA
14 Night Eastern Caribbean Cruise from Boston, MA
Holland America Line Zuiderdam
Departure Port: Boston, MA
OCG Class
Premium
Cruises to: SAN JUAN, PUERTO RICO; ST. THOMAS, U.S.V.I.; PHILIPSBURG, SINT MAARTEN; CASTRIES, SAINT LUCIA; BRIDGETOWN, BARBADOS; WILLEMSTAD, CURACAO; HALF MOON CAY, BAHAMAS more ...
DepartingInteriorOceanviewBalconySuite
Oct 18, 2025$393$893$1,393$2,553
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
Princess Cruises Majestic Princess
Departure Port: Fort Lauderdale, FL
OCG Class
Mainstream
Cruises to: COSTA MAYA (MAHAHUAL), MEXICO; ROATAN (MAHOGANY BAY, HONDURAS; COZUMEL, MEXICO; FT. LAUDERDALE, FLORIDA; CURACAO; ARUBA; ARUBA more ...
DepartingInteriorOceanviewBalconySuite
Nov 2, 2025$999-$1,502$2,049
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
Princess Cruises Majestic Princess
Departure Port: Fort Lauderdale, FL
OCG Class
Mainstream
Cruises to: CURACAO; ARUBA; ARUBA; FT. LAUDERDALE, FLORIDA; COSTA MAYA (MAHAHUAL), MEXICO; ROATAN (MAHOGANY BAY, HONDURAS; COZUMEL, MEXICO more ...
DepartingInteriorOceanviewBalconySuite
Nov 8, 2025$999-$1,545$2,049
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
14 Night Eastern Caribbean Cruise from Fort Lauderdale, FL
Princess Cruises Majestic Princess
Departure Port: Fort Lauderdale, FL
OCG Class
Mainstream
Cruises to: COSTA MAYA (MAHAHUAL), MEXICO; ROATAN (MAHOGANY BAY, HONDURAS; COZUMEL, MEXICO; FT. LAUDERDALE, FLORIDA; CURACAO; ARUBA; FT. LAUDERDALE, FLORIDA
DepartingInteriorOceanviewBalconySuite
Nov 30, 2025$959-$1,548$2,259

Sponsored Content

JDS Travel News JDS Viewpoints JDS Africa/MI