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Itineraries and cruises Windstar Cruises departing from Philipsburg February 2026 - 2027

  • 2025
December 2025
January 2026 February 2026 March 2026 April 2026 May 2026 June 2026 July 2026 August 2026 September 2026 October 2026 November 2026
7 cruises
sold out
Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados
Philipsburg Itinerary Caribbean
External from $7,838
price per person Taxes included
Wind Spirit | 28/02/2026
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, United States, Dominica, Saint Vincent and the Grenadines, Martinique, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $8,032
price per person Taxes included
Wind Spirit | 7/02/2026
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, United States, Dominica, Saint Vincent and the Grenadines, France, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $8,700
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 28/02/2026
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, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $8,718
price per person Taxes included
See the cruise Book Online Book Online
Wind Spirit | 14/02/2026
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
Caribbean: Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $8,718
price per person Taxes included
See the cruise Book Online Book Online
Wind Spirit | 21/02/2026
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
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, France, Saint Kitts and Nevis, Saint Barthelemy, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
External from $13,835
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 28/02/2026
Duration: 14 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Deshaies,
6. Basseterre,
7. Gustavia,
8. Philipsburg,
9. navigation,
10. Tortola Island,
11. Virgin Gorda,
12. Tortola Island,
13. Tortola Island,
14. Jost Van Dyke,
15. Gustavia,
16. Philipsburg
sold out
Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados, Antigua and Barbuda, Martinique
Philipsburg Itinerary Caribbean
External from $15,670
price per person Taxes included
Wind Spirit | 28/02/2026
Duration: 15 nights
Departure from: Philipsburg Landing: Bridgetown
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. navigation,
5. Les Saintes,
6. Roseau,
7. Mayreau,
8. Bridgetown,
9. navigation,
10. Basseterre,
11. Saint Johns,
12. Les Saintes,
13. Roseau,
14. Mayreau,
15. Fort de france,
16. Bridgetown
7 cruises