7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Seeker
DepartsFri, Feb 6th 2026
ReturnsFri, Feb 13th 2026
Nights7
Departing PortSan Juan
Ports of CallSan Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, 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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14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipStar Seeker
DepartsFri, Feb 6th 2026
ReturnsFri, Feb 20th 2026
Nights14
Departing PortSan Juan
Ports of CallSan Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, Admiralty Bay, Bequia, Mayreau, Soufriere Bay, Pointe a Pitre, Marigot, 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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14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipWind Spirit
DepartsSat, Feb 7th 2026
ReturnsSat, Feb 21st 2026
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, Charleston, Roseau, Pigeon Island, Pointe a Pitre, Gustavia, Basseterre, Philipsburg, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), 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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7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Spirit
DepartsSat, Feb 7th 2026
ReturnsSat, Feb 14th 2026
Nights7
Departing PortPhilpsburg
Ports of CallPhilpsburg, Charlestown, Roseau, Mayreau, Martinique, Basseterre, Gustavia, Philpsburg
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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14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipStar Seeker
DepartsFri, Feb 13th 2026
ReturnsFri, Feb 27th 2026
Nights14
Departing PortSan Juan
Ports of CallSan Juan, Admiralty Bay, Bequia, Mayreau, Soufriere Bay, Pointe a Pitre, Marigot, San Juan, St. John Island, Basseterre, Philipsburg, Gustavia, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, 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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18 Night Caribbean Cruise
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,…
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7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Seeker
DepartsFri, Feb 20th 2026
ReturnsFri, Feb 27th 2026
Nights7
Departing PortSan Juan
Ports of CallSan Juan, St. John Island, Basseterre, Philipsburg, Gustavia, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, 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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14 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Seeker
DepartsFri, Feb 20th 2026
ReturnsFri, Mar 6th 2026
Nights14
Departing PortSan Juan
Ports of CallSan Juan, St. John Island, Basseterre, Philipsburg, Gustavia, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, San Juan, Philipsburg, Pointe a Pitre, Soufriere Bay, Admiralty Bay, Bequia, Mayreau, 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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28 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Spirit
DepartsSat, Feb 21st 2026
ReturnsSat, Mar 21st 2026
Nights28
Departing PortPhilipsburg
Ports of CallPhilipsburg, St. John's, Road Bay, Anguilla, Leverick Bay, Virgin Gorda, Tortola (2 Days), Great Harbour, Jost Van Dyke BVI, Gustavia, Philipsburg, Basseterre, Gustavia, St. John's, Pointe a Pitre, Roseau, Mayreau, Bridgetown, Basseterre, St. John's, Pointe a Pitre, Roseau, Mayreau, Grande Anse, Bridgetown, Tobago Cays, Pigeon Island (2 Days), Castries, Cruising Pitons, Mayreau, Admiralty Bay, Bequia, Bridgetown
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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22 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Spirit
DepartsSat, Feb 21st 2026
ReturnsSun, Mar 15th 2026
Nights22
Departing PortPhilipsburg
Ports of CallPhilipsburg, St. John's, Road Bay, Anguilla, Leverick Bay, Virgin Gorda, Tortola (2 Days), Great Harbour, Jost Van Dyke BVI, Gustavia, Philipsburg, Basseterre, Gustavia, St. John's, Pointe a Pitre, Roseau, Mayreau, Bridgetown, Basseterre, St. John's, Pointe a Pitre, Roseau, Mayreau, Grande Anse, Bridgetown
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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14 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Spirit
DepartsSat, Feb 21st 2026
ReturnsSat, Mar 7th 2026
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, St. John's, Road Bay, Anguilla, Leverick Bay, Virgin Gorda, Tortola (2 Days), Great Harbour, Jost Van Dyke BVI, Gustavia, Philipsburg, Basseterre, Gustavia, St. John's, Pointe a Pitre, Roseau, Mayreau, Bridgetown
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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Ocean View
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Balcony
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14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipStar Seeker
DepartsFri, Feb 27th 2026
ReturnsFri, Mar 13th 2026
Nights14
Departing PortSan Juan
Ports of CallSan Juan, Philipsburg, Pointe a Pitre, Soufriere Bay, Admiralty Bay, Bequia, Mayreau, San Juan, St. John Island, Basseterre, Gustavia, Philipsburg, Great Harbour, Jost Van Dyke BVI, Leverick Bay, Virgin Gorda, 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…
Inside Cabin
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Ocean View
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Balcony
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Suite
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15 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Spirit
DepartsSat, Feb 28th 2026
ReturnsSun, Mar 15th 2026
Nights15
Departing PortPhilipsburg
Ports of CallPhilipsburg, Basseterre, Gustavia, Falmouth, Pointe a Pitre, Roseau, Mayreau, Bridgetown, Basseterre, St. John's, Pointe a Pitre, Roseau, Mayreau, Grande Anse, Bridgetown
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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Ocean View
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7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Spirit
DepartsSat, Feb 28th 2026
ReturnsSat, Mar 7th 2026
Nights7
Departing PortPhilipsburg
Ports of CallPhilipsburg, Basseterre, Gustavia, Little Bay, Pointe a Pitre, Roseau, Pigeon Island, Bridgetown
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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7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Feb 28th 2026
ReturnsSat, Mar 7th 2026
Nights7
Departing PortPhilipsburg
Ports of CallPhilipsburg, 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
Call for pricing
Balcony
Call for pricing
Suite
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14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Feb 28th 2026
ReturnsSat, Mar 14th 2026
Nights14
Departing PortPhilipsburg
Ports of CallPhilipsburg, 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
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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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. Pricing listed includes taxes and fees. Airfare is not included. Prices and itineraries are based on availability and are subject to change without notice.
