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Itineraries and cruises Windstar Cruises departing from Philipsburg February 2026

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December 2025
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January 2027 February 2027 March 2027
5 cruises
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, France, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $6,380
price per person Taxes included
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Wind Surf | 28 Feb 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Deshaies,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Caribbean: Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados
Philipsburg Itinerary Caribbean
External from $6,692
price per person Taxes included
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Wind Spirit | 28 Feb 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Bridgetown
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. navigation,
5. Les Saintes,
6. Roseau,
7. Mayreau,
8. Bridgetown
sold out
Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $7,136
price per person Taxes included
Wind Spirit | 21 Feb 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Saint Johns,
3. Tortola Island,
4. Virgin Gorda,
5. Tortola Island,
6. Tortola Island,
7. Jost Van Dyke,
8. Gustavia,
9. Philipsburg
: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Martinique, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary
External from $7,426
price per person Taxes included
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Wind Spirit | 7 Feb 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Fort de france,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Caribbean: Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $7,690
price per person Taxes included
See the cruise Book Online Book Online
Wind Spirit | 14 Feb 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Saint Johns,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
5 cruises