7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipStar Seeker
DepartsFri, Mar 6th 2026
ReturnsFri, Mar 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, Mar 6th 2026
ReturnsFri, Mar 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, Marigot, Pointe a Pitre, Mayreau, Admiralty Bay, Bequia, Pigeon Island, Cruising Pitons, 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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Ocean View
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Balcony
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Suite
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7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Mar 7th 2026
ReturnsSat, Mar 14th 2026
Nights7
Departing PortPhilipsburg
Ports of CallPhilipsburg, Falmouth, Road Bay, Anguilla, Leverick Bay, Virgin Gorda, Tortola (2 Days), Great Harbour, Jost Van Dyke BVI, 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,…
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14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Mar 14th 2026
ReturnsSat, Mar 28th 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, 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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Suite
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7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Mar 14th 2026
ReturnsSat, Mar 21st 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
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Ocean View
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Suite
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7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Mar 21st 2026
ReturnsSat, Mar 28th 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
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Balcony
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Suite
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14 Night Caribbean - Extended Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Mar 21st 2026
ReturnsSat, Apr 4th 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,…
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21 Night Trans-Atlantic Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Mar 28th 2026
ReturnsSat, Apr 18th 2026
Nights21
Departing PortPhilipsburg
Ports of CallPhilipsburg, St. John Island, Road Bay, Anguilla, Tortola, Great Harbour, Jost Van Dyke BVI (2 Days), Leverick Bay, Virgin Gorda, Gustavia, Philipsburg, Ponta Delgada, Lisbon
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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7 Night Caribbean Cruise
Cruise LineWindstar Cruises
ShipWind Surf
DepartsSat, Mar 28th 2026
ReturnsSat, Apr 4th 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
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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.
