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Cruises of Windstar Cruises in Sint Maarten

  • 2027
  • 2028
December 2026
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January 2028 February 2028 March 2028
64 cruises
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 $6,585
price per person Taxes included
See the cruise Book
Wind Surf | Dec 19, 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
Caribbean: Sint Maarten, Saint Barthelemy, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
External from $3,656
price per person Taxes included
See the cruise Book
Wind Surf | Dec 19, 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 $6,388
price per person Taxes included
See the cruise Book
Wind Surf | Dec 26, 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, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
External from $4,500
price per person Taxes included
See the cruise Book
Wind Surf | Dec 26, 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, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $3,203
price per person Taxes included
See the cruise Book
Wind Surf | Jan 2, 2027
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
Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy, United States, Guadeloupe, Saint Vincent and the Grenadines, Dominica, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
External from $5,961
price per person Taxes included
See the cruise Book
Wind Surf | Jan 2, 2027
Duration: 14 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,
10. Charlestown,
11. Les Saintes,
12. Mayreau,
13. Roseau,
14. Basseterre,
15. Gustavia,
16. Philipsburg
Caribbean: Sint Maarten, United States, Guadeloupe, Saint Vincent and the Grenadines, Dominica, Saint Kitts and Nevis, Saint Barthelemy, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
External from $6,651
price per person Taxes included
See the cruise Book
Wind Surf | Jan 9, 2027
Duration: 14 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Les Saintes,
4. Mayreau,
5. Roseau,
6. Basseterre,
7. Gustavia,
8. Philipsburg,
9. Tortola Island,
10. Tortola Island,
11. Jost Van Dyke,
12. Jost Van Dyke,
13. Virgin Gorda,
14. Gustavia,
15. navigation,
16. Philipsburg
Caribbean: Sint Maarten, United States, Guadeloupe, Saint Vincent and the Grenadines, Dominica, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $4,377
price per person Taxes included
See the cruise Book
Wind Surf | Jan 9, 2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Les Saintes,
4. Mayreau,
5. Roseau,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
External from $7,243
price per person Taxes included
See the cruise Book
Wind Surf | Jan 16, 2027
Duration: 14 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Tortola Island,
4. Jost Van Dyke,
5. Jost Van Dyke,
6. Virgin Gorda,
7. Gustavia,
8. navigation,
9. Philipsburg,
10. Charlestown,
11. Roseau,
12. Mayreau,
13. Les Saintes,
14. Basseterre,
15. Gustavia,
16. Philipsburg
Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $3,902
price per person Taxes included
See the cruise Book
Wind Surf | Jan 16, 2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Tortola Island,
4. Jost Van Dyke,
5. Jost Van Dyke,
6. Virgin Gorda,
7. Gustavia,
8. navigation,
9. Philipsburg
64 cruises