
All-Inclusive Package + Up to $200 Onboard Credit per stateroom + Save 5% when you pay in full
Offer valid from Thursday, September 18th 2025 to Friday, October 31st 2025
All-Inclusive Package + Up to $200 Onboard Credit per stateroom + Save 5% when you pay in full
Offer valid from Thursday, September 18th 2025 to Friday, October 31st 2025
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 4th 2026
ReturnsSat, Feb 28th 2026
Nights55
Departing PortPhilipsburg
Ports of CallPhilipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Basseterre, Little Bay, Gustavia, Pointe a Pitre, Roseau, Pigeon Island, Bridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon (2 Days), 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
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 new finishes and furnishings in suites and staterooms,…
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Suite
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Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 4th 2026
ReturnsSun, Jan 25th 2026
Nights21
Departing PortPhilpsburg
Ports of CallPhilpsburg, Falmouth, Road Bay, Sopers Hole, Great Harbour, Jost Van Dyke BVI (2 Days), Gustavia, Philpsburg, Basseterre, Gustavia, Terre-de-Haut, Mayreau, Kingstown, Bridgetown, Trois Ilets, Castries, Pigeon Island (2 Days), Port Elizabeth, Bequia, Mayreau, Saint George's, Bridgetown
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
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Ocean View
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Balcony
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Suite
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Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 4th 2026
ReturnsSun, Jan 11th 2026
Nights7
Departing PortPhilipsburg
Ports of CallPhilipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
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Balcony
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Suite
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Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 4th 2026
ReturnsSun, Jan 18th 2026
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Basseterre, Little Bay, Gustavia, Pointe a Pitre, Roseau, Pigeon Island, Bridgetown
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
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Ocean View
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Balcony
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Suite
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Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 4th 2026
ReturnsMon, Jan 26th 2026
Nights22
Departing PortPhilipsburg
Ports of CallPhilipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Basseterre, Gustavia, Little Bay, Gustavia, Deshaies, Roseau, Pigeon Island, Bridgetown, Grande Anse, Castries, Pigeon Island, Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
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Balcony
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Suite
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Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 4th 2026
ReturnsSun, Jan 11th 2026
Nights7
Departing PortPhilpsburg
Ports of CallPhilpsburg, Falmouth, Road Bay, Sopers Hole, Great Harbour, Jost Van Dyke BVI (2 Days), Gustavia, Philpsburg
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
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Balcony
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Suite
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Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 4th 2026
ReturnsSun, Feb 1st 2026
Nights28
Departing PortPhilipsburg
Ports of CallPhilipsburg, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Basseterre, Little Bay, Gustavia, Pointe a Pitre, Roseau, Pigeon Island, Bridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
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Balcony
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Suite
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Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 11th 2026
ReturnsSun, Jan 18th 2026
Nights7
Departing PortPhilipsburg
Ports of CallPhilipsburg, Basseterre, Little Bay, Gustavia, Deshaies, Roseau, Pigeon Island, Bridgetown
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
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Balcony
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Suite
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Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 11th 2026
ReturnsSun, Jan 25th 2026
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, Basseterre, Little Bay, Gustavia, Deshaies, Roseau, Pigeon Island, Bridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
Call for pricing
Balcony
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Suite
Call for pricing
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 18th 2026
ReturnsSun, Jan 25th 2026
Nights7
Departing PortBridgetown
Ports of CallBridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 18th 2026
ReturnsSun, Feb 1st 2026
Nights14
Departing PortBridgetown
Ports of CallBridgetown, Grande Anse, Castries, Pigeon Island (2 Days), Admiralty Bay, Bequia, Mayreau, St. George's, Bridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 25th 2026
ReturnsMon, Feb 9th 2026
Nights15
Departing PortBridgetown
Ports of CallBridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon (2 Days)
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Jan 25th 2026
ReturnsSun, Feb 1st 2026
Nights7
Departing PortBridgetown
Ports of CallBridgetown, Man-O-War, Tobago, Mayreau, Soufriere Bay, Kralendijk, Bonaire, Willemstad, Oranjestad
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Feb 1st 2026
ReturnsTue, Feb 17th 2026
Nights16
Departing PortOranjestad
Ports of CallOranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon (2 Days), Bocas Del Toro, San Andres Island, Roatan, Belize City, Costa Maya, Cozumel
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSun, Feb 1st 2026
ReturnsMon, Feb 9th 2026
Nights8
Departing PortOranjestad
Ports of CallOranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon (2 Days)
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
Cruise LineWindstar Cruises
ShipWind Surf
DepartsMon, Feb 9th 2026
ReturnsTue, Feb 17th 2026
Nights8
Departing PortColon
Ports of CallColon, Bocas Del Toro, San Andres Island, Roatan, Belize City, Costa Maya, Cozumel
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
Call for pricing
Balcony
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Suite
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Cruise LineWindstar Cruises
ShipWind Surf
DepartsMon, Feb 9th 2026
ReturnsSat, Feb 28th 2026
Nights19
Departing PortColon
Ports of CallColon, 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
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
Call for pricing
Cruise LineWindstar Cruises
ShipWind Surf
DepartsMon, Feb 9th 2026
ReturnsTue, Feb 17th 2026
Nights8
Departing PortColón, Panama
Ports of CallColón, Panama, Bocas Del Toro, San Andres Island, Roatan Bay Island, Belize City, Costa Maya, Cozumel
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
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Balcony
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Suite
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Cruise LineWindstar Cruises
ShipWind Surf
DepartsTue, Feb 17th 2026
ReturnsSat, Feb 28th 2026
Nights11
Departing PortCozumel
Ports of CallCozumel, Grand Cayman, Cayman Brac, Port Antonio, Santo Domingo, La Romana, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Philipsburg
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
Call for pricing
Ocean View
Call for pricing
Balcony
Call for pricing
Suite
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Cruise LineWindstar Cruises
ShipWind Surf
DepartsTue, Feb 17th 2026
ReturnsSat, Mar 7th 2026
Nights18
Departing PortCozumel
Ports of CallCozumel, 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
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 new finishes and furnishings in suites and staterooms,…
Inside Cabin
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Ocean View
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Balcony
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Suite
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Booking Window: Now - 10/31/25
Applicable Sailings: Star Breeze and Wind Star 2027 Tahiti voyages. Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages.
Terms & Conditions: For Windstar’s newly released Star Legend, Wind Surf and Wind Star 2026/2027 Caribbean and Latin America voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for 2026/2027 Caribbean and Latin America voyages. Ships’ registry: Bahamas.
For Windstar’s newly released Star Breeze and Wind Star 2027 Tahiti voyages, Windstar is offering a $200 shipboard credit per stateroom* and a free upgrade to our All-Inclusive package (valued at up to $99 per guest per day). *All fares mentioned are per person, in US dollars, cruise only, based on double occupancy in lowest category, and include non-discountable amounts. Single and Triple guests in a stateroom or suite are also eligible for this promotion, the shipboard credit will be awarded at $100 per guest. All-inclusive package includes Wi-Fi, and unlimited select beer, wine and cocktails, and gratuities. Government Taxes & Fees are additional and are published on Windstar's website. Offer is valid on new bookings only and subject to availability. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made, nor can this offer be applied retroactively. Shipboard credits are valid on the applicably purchased sailing only and are non-refundable with no cash value. Cancellation fees may apply; please see website for details. Fuel surcharges may be imposed or increased over time. Offer is capacity controlled and may be withdrawn or modified at Windstar’s discretion at any time. Information contained herein is accurate at time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruises are provided subject to the terms and conditions of the Passage Contract. Offer is valid for reservations booked by October 31, 2025 for Tahiti Star Breeze and Wind Star voyages. Ships’ registry: Bahamas.