October 2026 All Caribbean Cruises

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Showing 161 - 170 of 984 Cruises
7 Night Caribbean Cruise from San Juan, Puerto Rico
7 Night Caribbean Cruise from San Juan, Puerto Rico
Norwegian Cruise Line Norwegian Prima
Departure Port: San Juan, Puerto Rico
OCG Class
Mainstream
Cruises to: TORTOLA, BRITISH VIRGIN ISLANDS; BASSETERRE, SAINT KITTS - NEVIS; BRIDGETOWN, BARBADOS; ST LUCIA, SAINT LUCIA; PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES; ST THOMAS, VI; SAN JUAN, PR
DepartingInteriorOceanviewBalconySuite
Nov 22, 2026$1,559$1,629$1,629$1,779
Nov 29, 2026$1,299$1,379$1,529$1,779
7 Night Caribbean Cruise from San Juan, Puerto Rico
7 Night Caribbean Cruise from San Juan, Puerto Rico
The Ritz-Carlton Yacht Collection Evrima
Departure Port: San Juan, Puerto Rico
OCG Class
Premium
Cruises to: Cartagena; Cartagena; Panama City
DepartingInteriorOceanviewBalconySuite
Nov 12, 2026---$8,600
7 Night Caribbean Cruise from San Juan, Puerto Rico
7 Night Caribbean Cruise from San Juan, Puerto Rico
Virgin Voyages Valiant Lady
Departure Port: San Juan, Puerto Rico
OCG Class
Premium
Cruises to: Willemstad, Curacao; Oranjestad, Aruba; Fort-de-france, Martinique; Basseterre, Saint Kitts And Nevis; San Juan, Puerto Rico
DepartingInteriorOceanviewBalconySuite
Oct 31, 2026$1,113$1,323$1,533$4,123
7 Night Caribbean Cruise from San Juan, Puerto Rico
7 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
DepartingInteriorOceanviewBalconySuite
Nov 15, 2026-$3,739$4,649$5,909
7 Night Caribbean Cruise from San Juan, Puerto Rico
7 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
DepartingInteriorOceanviewBalconySuite
Nov 8, 2026-$2,126$2,857$4,152
Nov 22, 2026-$2,857$3,592$5,027
7 Night Caribbean Cruise from Santo Domingo, Dominican Republic
7 Night Caribbean Cruise from Santo Domingo, Dominican Republic
Costa Cruise Lines Costa Favolosa
Departure Port: Santo Domingo, Dominican Republic
OCG Class
Mainstream
Cruises to: Guadeloupe (Antilles); Martinique (Antilles); St. Kitts (Antilles); Antigua (Antilles); Road Harbour | Tortola; Santo Domingo (Dominican Republic)
DepartingInteriorOceanviewBalconySuite
Nov 30, 2026$1,199$1,319$1,619$1,819
7 Night Caribbean Cruise from St Maarten, St Martin/St Maarten
7 Night Caribbean Cruise from St Maarten, St Martin/St Maarten
Atlas Ocean Voyages World Navigator
Departure Port: St Maarten, St Martin/St Maarten
OCG Class
Expedition
Cruises to: Gustavia; Fort-de-France; Bridgetown
DepartingInteriorOceanviewBalconySuite
Oct 14, 2026---$5,899
7 Night Caribbean Cruise from Tampa, FL
7 Night Caribbean Cruise from Tampa, FL
Carnival Cruise Line Carnival Legend
Departure Port: Tampa, FL
OCG Class
Mainstream
Cruises to: Cozumel, Mexico (dock); Montego Bay, Jamaica (dock); Grand Cayman, Cayman Islands (tender); Tampa, Fl (dock)
DepartingInteriorOceanviewBalconySuite
Nov 29, 2026Contact cruise line for pricing & availability
7 Night Eastern Caribbean Cruise from Bridgetown, Barbados
7 Night Eastern Caribbean Cruise from Bridgetown, Barbados
Azamara Azamara Journey
Departure Port: Bridgetown, Barbados
OCG Class
Premium
Cruises to: CASTRIES; ROSEAU; BASSETERRE, ST.KITTS; PHILIPSBURG; GUSTAVIA; SAN JUAN; SAN JUAN
DepartingInteriorOceanviewBalconySuite
Nov 28, 2026$1,390$1,870$2,530$4,140
7 Night Eastern Caribbean Cruise from Bridgetown, Barbados
7 Night Eastern Caribbean Cruise from Bridgetown, Barbados
Azamara Azamara Journey
Departure Port: Bridgetown, Barbados
OCG Class
Premium
Cruises to: CASTRIES; ROSEAU; BASSETERRE, ST.KITTS; PHILIPSBURG; ROAD TOWN, TORTOLA; SAN JUAN; SAN JUAN
DepartingInteriorOceanviewBalconySuite
Nov 14, 2026$1,390$1,870$2,530$4,140