All Caribbean Cruises on Windstar Cruises

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Showing 1 - 10 of 33 Cruises
6 Night Caribbean Cruise from Aruba
6 Night Caribbean Cruise from Aruba
Windstar Cruises Star Pride
Departure Port: Aruba
OCG Class
Luxury
Cruises to: WILLEMSTAD, CURACAO; GUSTAVIA, ST. BARTHELEMY; SAN JUAN; SAN JUAN
DepartingInteriorOceanviewBalconySuite
Mar 6, 2028Contact cruise line for pricing & availability
6 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
6 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
Windstar Cruises Wind Surf
Departure Port: Philipsburg, St Maarten, St Martin/St Maarten
OCG Class
Luxury
Cruises to: GUSTAVIA, ST. BARTHELEMY; SOPER'S HOLE, TORTOLA, BVI; PHILIPSBURG, ST. MAARTEN; PHILIPSBURG, ST. MAARTEN
DepartingInteriorOceanviewBalconySuite
Jan 3, 2028-$1,812-$2,532
6 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
6 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
Windstar Cruises Wind Surf
Departure Port: Philipsburg, St Maarten, St Martin/St Maarten
OCG Class
Luxury
Cruises to: FALMOUTH HARBOUR, ANTIGUA; SOPER'S HOLE, TORTOLA, BVI; GUSTAVIA, ST. BARTHELEMY; PHILIPSBURG, ST. MAARTEN
DepartingInteriorOceanviewBalconySuite
Mar 13, 2027-$1,812-$2,532
7 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
7 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
Windstar Cruises Wind Surf
Departure Port: Philipsburg, St Maarten, St Martin/St Maarten
OCG Class
Luxury
Cruises to: GUSTAVIA, ST. BARTHELEMY; FALMOUTH HARBOUR, ANTIGUA; SOPER'S HOLE, TORTOLA, BVI; PHILIPSBURG, ST. MAARTEN; PHILIPSBURG, ST. MAARTEN
DepartingInteriorOceanviewBalconySuite
Dec 19, 2026-$2,345-$3,185
7 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
7 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
Windstar Cruises Wind Surf
Departure Port: Philipsburg, St Maarten, St Martin/St Maarten
OCG Class
Luxury
Cruises to: ROSEAU, DOMINICA; BASSETERRE, ST. KITTS; GUSTAVIA, ST. BARTHELEMY; PHILIPSBURG, ST. MAARTEN; PHILIPSBURG, ST. MAARTEN
DepartingInteriorOceanviewBalconySuite
Jan 9, 2027-$2,121-$2,961
7 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
7 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
Windstar Cruises Wind Surf
Departure Port: Philipsburg, St Maarten, St Martin/St Maarten
OCG Class
Luxury
Cruises to: ROSEAU, DOMINICA; BASSETERRE, ST. KITTS; GUSTAVIA, ST. BARTHELEMY; PHILIPSBURG, ST. MAARTEN; PHILIPSBURG, ST. MAARTEN
DepartingInteriorOceanviewBalconySuite
Jan 23, 2027-$2,121-$2,961
Mar 6, 2027-$2,121-$2,961
Mar 20, 2027-$2,191-$3,031
7 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
7 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
Windstar Cruises Wind Surf
Departure Port: Philipsburg, St Maarten, St Martin/St Maarten
OCG Class
Luxury
Cruises to: SOPER'S HOLE, TORTOLA, BVI; GUSTAVIA, ST. BARTHELEMY; FALMOUTH HARBOUR, ANTIGUA; PHILIPSBURG, ST. MAARTEN; PHILIPSBURG, ST. MAARTEN
DepartingInteriorOceanviewBalconySuite
Jan 16, 2027-$2,121-$2,961
7 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
7 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
Windstar Cruises Wind Surf
Departure Port: Philipsburg, St Maarten, St Martin/St Maarten
OCG Class
Luxury
Cruises to: FALMOUTH HARBOUR, ANTIGUA; SOPER'S HOLE, TORTOLA, BVI; GUSTAVIA, ST. BARTHELEMY; PHILIPSBURG, ST. MAARTEN; PHILIPSBURG, ST. MAARTEN
DepartingInteriorOceanviewBalconySuite
Jan 2, 2027-$2,131-$2,971
7 Night Caribbean Cruise from San Juan, Puerto Rico
7 Night Caribbean Cruise from San Juan, Puerto Rico
Windstar Cruises 3tar Legend
Departure Port: San Juan, Puerto Rico
OCG Class
Luxury
Cruises to: GUSTAVIA, ST. BARTHELEMY; BASSETERRE, ST. KITTS; PHILIPSBURG, ST. MAARTEN; SAN JUAN
DepartingInteriorOceanviewBalconySuite
Jan 3, 2028-$1,951$3,246$5,311
7 Night Caribbean Cruise from San Juan, Puerto Rico
7 Night Caribbean Cruise from San Juan, Puerto Rico
Windstar Cruises 3tar Legend
Departure Port: San Juan, Puerto Rico
OCG Class
Luxury
Cruises to: BASSETERRE, ST. KITTS; GUSTAVIA, ST. BARTHELEMY; PHILIPSBURG, ST. MAARTEN; SAN JUAN
DepartingInteriorOceanviewBalconySuite
Dec 20, 2027-$2,129$3,389$5,489
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