October 2026 All Caribbean Cruises

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15 Night Caribbean Cruise from Southampton, England
15 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; BRIDGETOWN, BARBADOS
DepartingInteriorOceanviewBalconySuite
Oct 23, 2026Contact cruise line for pricing & availability
15 Night Caribbean Cruise from Southampton, England
15 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; BRIDGETOWN, BARBADOS
DepartingInteriorOceanviewBalconySuite
Oct 30, 2026Contact cruise line for pricing & availability
15 Night Eastern Caribbean Cruise from Miami, FL
15 Night Eastern Caribbean Cruise from Miami, FL
Regent Seven Seas Cruises Seven Seas Splendor
Departure Port: Miami, FL
OCG Class
Luxury
Cruises to: WILLEMSTAD; MONTEGO BAY; GEORGE TOWN; ROATAN; COZUMEL; HOUSTON (GALVESTON)
DepartingInteriorOceanviewBalconySuite
Nov 15, 2026---$8,452
15 Night Eastern Caribbean Cruise from Miami, FL
15 Night Eastern Caribbean Cruise from Miami, FL
Seabourn Seabourn Ovation
Departure Port: Miami, FL
OCG Class
Luxury
Cruises to: SAN JUAN, PUERTO RICO; CARAMBOLA BEACH, SAINT KITTS AND NEVIS; ROSEAU, DOMINICA; BARBADOS; RODNEY BAY, SAINT LUCIA; ST. JOHNS, ANTIGUA AND BARBUDA; CARAMBOLA BEACH, SAINT KITTS AND NEVIS more ...
DepartingInteriorOceanviewBalconySuite
Nov 20, 2026---$5,539
15 Night Western Caribbean Cruise from Miami, FL
15 Night Western Caribbean Cruise from Miami, FL
MSC Cruises MSC Poesia
Departure Port: Miami, FL
OCG Class
Mainstream
Cruises to: George Town Cayman Islands; Ocho Rios Jamaica; Miami Florida; Oranjestad Aruba; Willemstad Cura §ao; Ocho Rios Jamaica; Miami Florida
DepartingInteriorOceanviewBalconySuite
Oct 17, 2026$761$951$1,321$7,543
16 Night Eastern Caribbean Cruise from Montreal, PQ
16 Night Eastern Caribbean Cruise from Montreal, PQ
Regent Seven Seas Cruises Seven Seas Splendor
Departure Port: Montreal, PQ
OCG Class
Luxury
Cruises to: QUEBEC CITY; SAGUENAY; SYDNEY; HALIFAX; PHILIPSBURG; ST. JOHN'S; BASSETERRE more ...
DepartingInteriorOceanviewBalconySuite
Oct 30, 2026---$10,573
17 Night Southern Caribbean Cruise from Miami, FL
17 Night Southern Caribbean Cruise from Miami, FL
Holland America Line Zuiderdam
Departure Port: Miami, FL
OCG Class
Premium
Cruises to: WILLEMSTAD, CURACAO; ORANJESTAD, ARUBA; RELAXAWAY HALF MOON CAY, BAHAMAS; MIAMI, FLORIDA, US; KEY WEST, FLORIDA, US; OCHO RIOS, JAMAICA; GEORGETOWN, CAYMAN ISLANDS more ...
DepartingInteriorOceanviewBalconySuite
Nov 11, 2026$499$679$1,039$2,339
18 Night Caribbean Cruise from New York, NY
18 Night Caribbean Cruise from New York, NY
Cunard Line Queen Mary 2
Departure Port: New York, NY
OCG Class
Premium
Cruises to: ST THOMAS, VIRGIN ISLANDS, U.S; ROAD TOWN, TORTOLA; BASSETERRE, ST KITTS; PHILIPSBURG, ST MAARTEN; NEW YORK, NY, USA; SOUTHAMPTON, ENGLAND, UK
DepartingInteriorOceanviewBalconySuite
Nov 17, 2026$1,503$2,214$2,556-
18 Night Caribbean Cruise from Southampton, England
18 Night Caribbean Cruise from Southampton, England
Cunard Line Queen Mary 2
Departure Port: Southampton, England
OCG Class
Premium
Cruises to: NEW YORK, NY, USA; ST THOMAS, VIRGIN ISLANDS, U.S; ROAD TOWN, TORTOLA; BASSETERRE, ST KITTS; PHILIPSBURG, ST MAARTEN; NEW YORK, NY, USA
DepartingInteriorOceanviewBalconySuite
Nov 10, 2026$1,254--$10,015
18 Night Western Caribbean Cruise from Miami, FL
18 Night Western Caribbean Cruise from Miami, FL
Explora Journeys Explora I
Departure Port: Miami, FL
OCG Class
Luxury
Cruises to: Merida (Progreso); Roatan Island; Belize City; Miami; Willemstad; Oranjestad; Santa Marta more ...
DepartingInteriorOceanviewBalconySuite
Nov 17, 2026---$10,880

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