Complimentary All-Inclusive Package on select sailings

Includes wine, beer and cocktails, Wi-Fi, and gratuities — worth up to $1,350 per couple on a 7-night cruise

 

 

7 Night Caribbean Cruise

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,…

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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.

21 Night Caribbean - Extended Cruise

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,…

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Ocean View

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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

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

22 Night Caribbean - Extended Cruise

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

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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.

15 Night European Coast Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsSun, Jan 4th 2026

ReturnsMon, Jan 19th 2026

Nights15

Departing PortVenice

Ports of CallVenice (2 Days), Zadar, Dubrovnik (2 Days), Messina, Naples, Civitavecchia (Rome), Livorno (Florence,Pisa) (2 Days), Genoa, Nice (2 Days), Barcelona (2 Days)

 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.

11 Night South American Coast Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsWed, Jan 7th 2026

ReturnsSun, Jan 18th 2026

Nights11

Departing PortLima (Callao)

Ports of CallLima (Callao) (2 Days), Banana Coast (Trujillo), Machala, Guayaquil (2 Days), Manta, Colón, Panama

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 South Pacific Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsThu, Jan 8th 2026

ReturnsThu, Jan 15th 2026

Nights7

Departing PortPapeete

Ports of CallPapeete (2 Days), Moorea, Raiatea (2 Days), Motu Mahaea, Society Islands, Vaitape, Bora Bora, French Polynesia (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.

6 Night South Pacific Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsFri, Jan 9th 2026

ReturnsThu, Jan 15th 2026

Nights6

Departing PortMoorea

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

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.

10 Night Canary Islands Cruise

Cruise LineWindstar Cruises

ShipWind Star

DepartsFri, Jan 9th 2026

ReturnsMon, Jan 19th 2026

Nights10

Departing PortSanta Cruz de Tenerife

Ports of CallSanta Cruz de Tenerife, San Sebastian, La Gomera, Santa Cruz de la Palma, Funchal, Madeira (2 Days), Lanzarote, Las Palmas, Gran Canaria (2 Days), Santa Cruz de Tenerife

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.

6 Night Panama Canal Cruise

Cruise LineWindstar Cruises

ShipStar Pride

DepartsSun, Jan 11th 2026

ReturnsSat, Jan 17th 2026

Nights6

Departing PortBalboa

Ports of CallBalboa, Exit Panama Canal, Bocas Del Toro, San Blas, Cartagena, Oranjestad

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 Africa - Middle East - India Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsSun, Jan 11th 2026

ReturnsMon, Jan 19th 2026

Nights8

Departing PortMuscat

Ports of CallMuscat, Al Fujayrah, Al Khasab, Abu Dhabi (2 Days), Doha (2 Days), Sir Bani Yas, Dubai

 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

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

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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.

14 Night Caribbean Cruise

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

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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.

16 Night European Coast Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsMon, Jan 12th 2026

ReturnsWed, Jan 28th 2026

Nights16

Departing PortCivitavecchia (Rome)

Ports of CallCivitavecchia (Rome), Livorno (Florence,Pisa) (2 Days), Genoa, Nice, Marseille, Barcelona (3 Days), Valencia, Cartagena, Gibraltar, Malaga (2 Days), Palma de Mallorca, Spanish Isle, Barcelona

 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 European Coast Cruise

Cruise LineWindstar Cruises

ShipStar Legend

DepartsMon, Jan 12th 2026

ReturnsMon, Jan 19th 2026

Nights7

Departing PortCivitavecchia (Rome)

Ports of CallCivitavecchia (Rome), Livorno (Florence,Pisa) (2 Days), Genoa, Nice, Marseille, Barcelona (2 Days)

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

17 Night Caribbean - Extended Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsWed, Jan 14th 2026

ReturnsSat, Jan 31st 2026

Nights17

Departing PortPhilipsburg

Ports of CallPhilipsburg, Little Bay, Roseau, Castries, Mayreau, St. George's, Admiralty Bay, Bequia, Grande Anse, Pointe a Pitre, Gustavia, Philipsburg, Tortola, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Gustavia, Road Bay, Anguilla, Falmouth, Philipsburg

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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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.

10 Night Caribbean Cruise

Cruise LineWindstar Cruises

ShipWind Spirit

DepartsWed, Jan 14th 2026

ReturnsSat, Jan 24th 2026

Nights10

Departing PortPhilipsburg

Ports of CallPhilipsburg, Basseterre, Roseau, Castries, Grande Anse, Pointe a Pitre, Charleston, Leverick Bay, Virgin Gorda, Great Harbour, Jost Van Dyke BVI, Gustavia, Philipsburg

With wide open, teak decks, the Wind Spirit is truly remarkable for a ship of its size. Plenty of spacious public places mean you can easily socialise with friends or just enjoy a quiet drink. Wind Spirit offers two primary dining venues. AmphorA Restaura…

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.

14 Night South Pacific Cruise

Cruise LineWindstar Cruises

ShipStar Breeze

DepartsThu, Jan 15th 2026

ReturnsThu, Jan 29th 2026

Nights14

Departing PortPapeete

Ports of CallPapeete (2 Days), Fakarava, Omoa, Atuona, Hiva Oa, Taiohae, Rangiroa Atoll, Motu Mahaea, Society Islands, Vaitape, Bora Bora, French Polynesia (2 Days), Moorea, Papeete (2 Days)

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…

Inside Cabin

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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 Seeker

DepartsThu, Jan 15th 2026

ReturnsFri, Jan 23rd 2026

Nights8

Departing PortMiami

Ports of CallMiami, Puerto Plata, Santo Domingo, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, Tortola, San Juan

Coming Dec. 2025, Star Seeker will be our first-ever Star Class new build, followed by Star Explorer in Dec. 2026. Serving 224 guests, each ship will feature 112 suites with full private verandas and infinity windows. They’ll also com…

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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

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

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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.