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Itineraries and cruises Windstar Cruises set offing from Philipsburg December 2026 - 2027

January 2026 February 2026 March 2026 April 2026 May 2026 June 2026 July 2026 August 2026 September 2026 October 2026 November 2026 December 2026
4 cruises
Caribbean: Sint Maarten, Saint Barthelemy, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
External from £2,977
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 26 Dec 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Gustavia,
3. Charlestown,
4. Roseau,
5. Mayreau,
6. Les Saintes,
7. Basseterre,
8. Philipsburg
Caribbean: Sint Maarten, Saint Barthelemy, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
External from £3,080
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 19 Dec 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Gustavia,
3. navigation,
4. Tortola Island,
5. Tortola Island,
6. Jost Van Dyke,
7. Jost Van Dyke,
8. Virgin Gorda,
9. Philipsburg
Caribbean: Sint Maarten, Saint Barthelemy, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
External from £4,636
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 26 Dec 2026
Duration: 14 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Gustavia,
3. Charlestown,
4. Roseau,
5. Mayreau,
6. Les Saintes,
7. Basseterre,
8. Philipsburg,
9. navigation,
10. Tortola Island,
11. Tortola Island,
12. Jost Van Dyke,
13. Jost Van Dyke,
14. Virgin Gorda,
15. Gustavia,
16. Philipsburg
Caribbean: Sint Maarten, Saint Barthelemy, British Virgin Islands, Virgin Islands, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
External from £4,814
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 19 Dec 2026
Duration: 14 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Gustavia,
3. navigation,
4. Tortola Island,
5. Tortola Island,
6. Jost Van Dyke,
7. Jost Van Dyke,
8. Virgin Gorda,
9. Philipsburg,
10. Gustavia,
11. Charlestown,
12. Roseau,
13. Mayreau,
14. Les Saintes,
15. Basseterre,
16. Philipsburg
4 cruises