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Itineraries and cruises Windstar Cruises departing from Philipsburg January 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
Caribbean: Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados
Philipsburg Itinerary Caribbean
External from $5,351
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 11/01/2026
Duration: 7 nights
Departure from: Philipsburg Landing: Bridgetown
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. Saint Johns,
5. Les Saintes,
6. Roseau,
7. Mayreau,
8. Bridgetown
Caribbean: Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $7,318
price per person Taxes included
See the cruise Book Online Book Online
Wind Spirit | 31/01/2026
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, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $7,318
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 4/01/2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. navigation,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
sold out
Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $7,718
price per person Taxes included
Wind Spirit | 24/01/2026
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
sold out
Sint Maarten, Saint Kitts and Nevis, Dominica, Saint Lucia, Martinique, Guadeloupe, United States, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $11,663
price per person Taxes included
Wind Spirit | 14/01/2026
Duration: 10 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Roseau,
4. Castries,
5. Fort de france,
6. Les Saintes,
7. Charlestown,
8. Virgin Gorda,
9. Jost Van Dyke,
10. Gustavia,
11. Philipsburg
Caribbean: Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados, Martinique, Saint Lucia, Sri Lanka, Grenada
Philipsburg Itinerary Caribbean
External from $12,915
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 11/01/2026
Duration: 14 nights
Departure from: Philipsburg Landing: Bridgetown
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. Saint Johns,
5. Les Saintes,
6. Roseau,
7. Mayreau,
8. Bridgetown,
9. Fort de france,
10. Castries,
11. Pigeon Island,
12. Pigeon Island,
13. Bequia,
14. Mayreau,
15. Saint George,
16. Bridgetown
Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Antigua and Barbuda, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Barbados
Philipsburg Itinerary Caribbean
External from $13,091
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 4/01/2026
Duration: 14 nights
Departure from: Philipsburg Landing: Bridgetown
Itinerary:
1. Philipsburg,
2. navigation,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg,
10. Basseterre,
11. Gustavia,
12. Saint Johns,
13. Les Saintes,
14. Roseau,
15. Mayreau,
16. Bridgetown
7 cruises