October 2026 Windstar Cruises Star Pride Cruises

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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
8 Night Caribbean Cruise from Boston, MA
8 Night Caribbean Cruise from Boston, MA
Windstar Cruises Star Pride
Departure Port: Boston, MA
OCG Class
Luxury
Cruises to: HAMILTON; HAMILTON; ST GEORGE'S BERMUDA; ST GEORGE'S BERMUDA; SAN JUAN; SAN JUAN
DepartingInteriorOceanviewBalconySuite
Oct 20, 2026-$2,608$3,288$5,168
11 Night Eastern Seaboard Cruise from Montreal, PQ
11 Night Eastern Seaboard Cruise from Montreal, PQ
Windstar Cruises Star Pride
Departure Port: Montreal, PQ
OCG Class
Luxury
Cruises to: CAPAUX MEULES, MAGDALEN ISLAND, QC; PORTLAND, ME
DepartingInteriorOceanviewBalconySuite
Oct 9, 2026-$4,956$7,321$11,006
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
19 Night Eastern Seaboard Cruise from Montreal, PQ
19 Night Eastern Seaboard Cruise from Montreal, PQ
Windstar Cruises Star Pride
Departure Port: Montreal, PQ
OCG Class
Luxury
Cruises to: CAPAUX MEULES, MAGDALEN ISLAND, QC; PORTLAND, ME; HAMILTON; HAMILTON; ST GEORGE'S BERMUDA; ST GEORGE'S BERMUDA; SAN JUAN more ...
DepartingInteriorOceanviewBalconySuite
Oct 9, 2026Contact cruise line for pricing & availability
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