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8-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
Ports of Call: Oranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon (2 Days)
Departs: Sun. 2/1/26     Returns: Mon. 2/9/26     Nights: 8
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all... expand Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Signature Exclusive Collection Offer (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
Additional Sailing Dates
2026 Departures: 2/9
2027 Departures: 1/18
Windstar Cruises
 


16-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
Ports of Call: Oranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon (2 Days), Bocas Del Toro, San Andres Island, Roatan, Belize City, Costa Maya, Cozumel
Departs: Sun. 2/1/26     Returns: Tue. 2/17/26     Nights: 16
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all... expand Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
 
Windstar Cruises
 


7-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
Ports of Call: Philipsburg, Charleston, Roseau, Pigeon Island, Pointe a Pitre, Gustavia, Basseterre, Philipsburg
Departs: Sat. 2/7/26     Returns: Sat. 2/14/26     Nights: 7
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all... expand Expand
Additional Sailing Dates
2025 Departures: 12/7, 12/14, 12/14, 12/21, 12/28, 12/28
2026 Departures: 1/4, 1/4, 1/11, 1/18, 1/24, 1/25, 2/28, 3/7, 3/14, 3/21, 3/28, 3/28
Windstar Cruises
 


8-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
Ports of Call: Colon, Bocas Del Toro, San Andres Island, Roatan, Belize City, Costa Maya, Cozumel
Departs: Mon. 2/9/26     Returns: Tue. 2/17/26     Nights: 8
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all... expand Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
Additional Sailing Dates
2026 Departures: 2/1
2027 Departures: 1/18
Windstar Cruises
 


19-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
Ports of Call: Colon, Bocas Del Toro, San Andres Island, Roatan, Belize City, Costa Maya, Cozumel, Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Philipsburg
Departs: Mon. 2/9/26     Returns: Sat. 2/28/26     Nights: 19
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all... expand Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
 
Windstar Cruises
 


11-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
Ports of Call: Cozumel, Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Philipsburg
Departs: Tue. 2/17/26     Returns: Sat. 2/28/26     Nights: 11
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all... expand Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
 
Windstar Cruises
 


18-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
Ports of Call: Cozumel, Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Philipsburg, Charleston, Roseau, Pigeon Island, Pointe a Pitre, Gustavia, Basseterre, Philipsburg
Departs: Tue. 2/17/26     Returns: Sat. 3/7/26     Nights: 18
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all... expand Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
 
Windstar Cruises
 


7-Night Caribbean (Caribbean - All)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
Ports of Call: Philipsburg, Charleston, Roseau, Pigeon Island, Pointe a Pitre, Gustavia, Basseterre, Philipsburg
Departs: Sat. 2/28/26     Returns: Sat. 3/7/26     Nights: 7
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all... expand Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
Additional Sailing Dates
2025 Departures: 12/7, 12/14, 12/14, 12/21, 12/28, 12/28
2026 Departures: 1/4, 1/4, 1/11, 1/18, 1/24, 1/25, 2/7, 3/7, 3/14, 3/21, 3/28, 3/28
Windstar Cruises
 


14-Night Caribbean (Caribbean - Extended)

Wind_Surf
Cruise Line: Windstar Cruises    Ship: Wind Surf
Ports of Call: Philipsburg, Charleston, Roseau, Pigeon Island, Pointe a Pitre, Gustavia, Basseterre, Philipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg
Departs: Sat. 2/28/26     Returns: Sat. 3/14/26     Nights: 14
On any day, their 342-guest flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. And her beauty is far more than skin deep. Starting with all... expand Expand
Special Sale: Travel Is Better When You're All-In (view details)Special Sale: Early Booking Offer - Tropics 2026/2027 & Tahiti 2027 (view details)Special Sale: Ways to Winter Sales Event (view details)
Additional Sailing Dates
2025 Departures: 12/7, 12/14, 12/21
2026 Departures: 3/14, 3/21
Windstar Cruises
 


Prices are per person, double occupancy, cruise only and on select sailings. Prices shown are for stateroom categories as noted and are shown in US Dollars. Government taxes and fees are additional. Airfare is not included. Prices and itineraries are based on availability and are subject to change without notice.