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Itineraries and cruises Windstar Cruises departing from Philipsburg January 2026

  • 2024
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  • 2026
December 2024
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5 cruises

Caribbean: Sint Maarten, Antigua and Barbuda, United Kingdom, British Virgin Islands, Virgin Islands, Saint Barthelemy

favorite
Philipsburg Itinerary Caribbean
from R 51 284,41
price per person Taxes included
16 reservations in 36 hours
See the cruise Book
Wind Surf | 04 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg

Caribbean: Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Sri Lanka, Saint Vincent and the Grenadines, Barbados

favorite
Philipsburg Itinerary Caribbean
from R 51 795,29
price per person Taxes included
18 reservations in 36 hours
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Wind Surf | 11 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Bridgetown
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. St. John ,
5. Les Saintes,
6. Pigeon Island,
7. Kingstown,
8. Bridgetown

Caribbean: Sint Maarten, Saint Kitts and Nevis, Dominica, Saint Lucia, Martinique, Guadeloupe, United States, British Virgin Islands, Virgin Islands, Saint Barthelemy

favorite
Philipsburg Itinerary Caribbean
from R 71 385,54
price per person Taxes included
19 reservations in 36 hours
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Wind Spirit | 14 Jan 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, Virgin Islands, United Kingdom, British Virgin Islands, Saint Barthelemy

favorite
Philipsburg Itinerary Caribbean
from R 52 266,87
price per person Taxes included
19 reservations in 36 hours
See the cruise Book
Wind Spirit | 24 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. St. John ,
3. Anguilla,
4. Virgin Gorda,
5. Tortola Island,
6. Tortola Island,
7. Jost Van Dyke,
8. Gustavia,
9. Philipsburg

Caribbean: Sint Maarten, Virgin Islands, United Kingdom, British Virgin Islands, Saint Barthelemy

favorite
Philipsburg Itinerary Caribbean
from R 50 301,95
price per person Taxes included
21 reservations in 36 hours
See the cruise Book
Wind Spirit | 31 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. St. John ,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
5 cruises