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6 Night Tahiti Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Dec 11th 2026

ReturnsThu, Dec 17th 2026

Nights6

Departing PortMoorea

Ports of CallMoorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Bora Bora (2 Days), Huahine, Papeete

Star Breeze is large enough to pamper and entertain you, yet small enough to tuck into delightful tiny harbors and hidden coves that others can’t reach. In 2021, this  all-suite ship will have completed a renovation as part of t…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsSat, Dec 12th 2026

ReturnsSat, Dec 19th 2026

Nights7

Departing PortPuerto Caldera

Ports of CallPuerto Caldera, Puerto Quepos, Puerto Jimenez, Costa Rica, Isla Parida, Panama, Balboa, Panama Canal Daylight Transit, Panama, Colon

Wind Star features wide open, teak decks—quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda. All staterooms have ocean views, queen beds, flat-screen TV with DVD p…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

8 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsSat, Dec 12th 2026

ReturnsSun, Dec 20th 2026

Nights8

Departing PortOranjestad

Ports of CallOranjestad, Cartagena (2 Days), Bocas Del Toro, San Blas, Panama Canal Daylight Transit, Panama, Balboa

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

16 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsSat, Dec 12th 2026

ReturnsMon, Dec 28th 2026

Nights16

Departing PortOranjestad

Ports of CallOranjestad, Cartagena (2 Days), Bocas Del Toro, San Blas, Panama Canal Daylight Transit, Panama, Balboa, Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera, Curu, Costa Rica, Playa Flamingo, Puerto Caldera

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 13th 2026

ReturnsSun, Dec 20th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean - Southern Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 13th 2026

ReturnsSun, Dec 27th 2026

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsSat, Dec 19th 2026

ReturnsSat, Dec 26th 2026

Nights7

Departing PortColon

Ports of CallColon, Panama Canal Daylight Transit, Panama, Balboa (2 Days), Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera

Wind Star features wide open, teak decks—quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda. All staterooms have ocean views, queen beds, flat-screen TV with DVD p…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Dec 19th 2026

ReturnsSat, Dec 26th 2026

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, Gustavia, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), 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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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Dec 19th 2026

ReturnsSat, Jan 2nd 2027

Nights14

Departing PortPhilipsburg

Ports of CallPhilipsburg, Gustavia, Falmouth, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Philipsburg, Gustavia, Charlestown, Roseau, Mayreau, Pointe a Pitre, 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,…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean - Southern Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 20th 2026

ReturnsSun, Jan 3rd 2027

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean - Southern Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 20th 2026

ReturnsSun, Dec 27th 2026

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

8 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsSun, Dec 20th 2026

ReturnsMon, Dec 28th 2026

Nights8

Departing PortBalboa

Ports of CallBalboa, Isla Parida, Panama, Puerto Jimenez, Costa Rica, Puerto Quepos, Puerto Caldera, Curu, Costa Rica, Playa Flamingo, Puerto Caldera

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Dec 26th 2026

ReturnsSat, Jan 2nd 2027

Nights7

Departing PortPhilipsburg

Ports of CallPhilipsburg, Gustavia, Charlestown, Roseau, Mayreau, Pointe a Pitre, 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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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean - Extended Cruise

Cruise LineWindstar Cruises

ShipWind Surf

DepartsSat, Dec 26th 2026

ReturnsSat, Jan 9th 2027

Nights14

Departing PortPhilipsburg

Ports of CallPhilipsburg, Gustavia, Charlestown, Roseau, Mayreau, Pointe a Pitre, Basseterre, Philipsburg, 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

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Ocean View

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Balcony

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Suite

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsSat, Dec 26th 2026

ReturnsSat, Jan 2nd 2027

Nights7

Departing PortPuerto Caldera

Ports of CallPuerto Caldera, Puerto Quepos, Puerto Jimenez, Costa Rica, Isla Parida, Panama, Balboa, Panama Canal Daylight Transit, Panama, Colon

Wind Star features wide open, teak decks—quite unusual for small ships. Guests will find hidden nooks for private moments giving them a feeling of being on their own private veranda. All staterooms have ocean views, queen beds, flat-screen TV with DVD p…

Inside Cabin

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Ocean View

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Balcony

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Suite

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

7 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 27th 2026

ReturnsSun, Jan 3rd 2027

Nights7

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

Inside Cabin

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Ocean View

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Balcony

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

14 Night Caribbean - Southern Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Dec 27th 2026

ReturnsSun, Jan 10th 2027

Nights14

Departing PortSan Juan

Ports of CallSan Juan, St. John Island, Gustavia, Basseterre, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, St. George's, Admiralty Bay, Bequia, Mayreau, Pointe a Pitre, St Maarten, San Juan

All Suite Ship  Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infin…

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

9 Night Mediterranean Cruise

Cruise LineWindstar Cruises

ShipStar Explorer

DepartsMon, Dec 28th 2026

ReturnsWed, Jan 6th 2027

Nights9

Departing PortBarcelona

Ports of CallBarcelona (2 Days), Valencia, Cartagena, Gibraltar, Malaga (2 Days), Palma de Mallorca, Spanish Isle, Barcelona

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.

8 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsMon, Dec 28th 2026

ReturnsTue, Jan 5th 2027

Nights8

Departing PortPuerto Caldera

Ports of CallPuerto Caldera (2 Days), Puerto Quepos, Puerto Jimenez, Costa Rica, Isla Parida, Panama, Balboa, Panama Canal Daylight Transit, Panama, Colon

 In 2021, this  all-suite ship will have completed a renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including two new dining venues, a new spa, infinity pool, and fitness ar…

Inside Cabin

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Ocean View

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Balcony

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Suite

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Some rates are not combinable with all promotions. Certain restrictions may apply. For full offer details, please contact your Cruise Planners Travel Advisor.