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Cruises of Windstar Cruises in Sint Maarten

40 cruises
sold out
Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $2,475
price per person Taxes included
Wind Surf | Dec 2, 2025
Duration: 5 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Jost Van Dyke,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Gustavia,
7. Philipsburg
Philipsburg Itinerary Caribbean
External from $2,958
price per person Taxes included
Wind Surf | Dec 2, 2025
Duration: 5 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Jost Van Dyke,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Gustavia,
7. Philipsburg
Philipsburg Itinerary Caribbean
External from $3,079
price per person Taxes included
Wind Surf | Dec 7, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
sold out
Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $2,838
price per person Taxes included
Wind Surf | Dec 7, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Philipsburg Itinerary Caribbean
External from $3,219
price per person Taxes included
Wind Surf | Dec 14, 2025
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, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $2,978
price per person Taxes included
Wind Surf | Dec 14, 2025
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, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $3,321
price per person Taxes included
Wind Surf | Dec 21, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Philipsburg Itinerary Caribbean
External from $3,924
price per person Taxes included
Wind Surf | Dec 21, 2025
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Philipsburg Itinerary Caribbean
External from $4,185
price per person Taxes included
Wind Surf | Dec 28, 2025
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, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $3,340
price per person Taxes included
Wind Surf | Dec 28, 2025
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
Philipsburg Itinerary Caribbean
External from $3,513
price per person Taxes included
Wind Surf | Jan 4, 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, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $3,151
price per person Taxes included
Wind Surf | Jan 4, 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, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Sri Lanka, Saint Vincent and the Grenadines, Barbados
Philipsburg Itinerary Caribbean
External from $3,182
price per person Taxes included
Wind Surf | Jan 11, 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
Philipsburg Itinerary Caribbean
External from $3,544
price per person Taxes included
Wind Surf | Jan 11, 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Bridgetown
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. Saint Johns,
5. Les Saintes,
6. Mayreau,
7. Kingstown,
8. Bridgetown
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 $5,955
price per person Taxes included
Wind Spirit | Jan 14, 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
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 $4,386
price per person Taxes included
Wind Spirit | Jan 14, 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
Philipsburg Itinerary Caribbean
External from $3,694
price per person Taxes included
Wind Spirit | Jan 24, 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, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $3,211
price per person Taxes included
Wind Spirit | Jan 24, 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
Philipsburg Itinerary Caribbean
External from $3,332
price per person Taxes included
Wind Spirit | Jan 31, 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
sold out
Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $3,090
price per person Taxes included
Wind Spirit | Jan 31, 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
sold out
Sint Maarten, United States, Dominica, Sri Lanka, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $3,159
price per person Taxes included
Wind Spirit | Feb 7, 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Pigeon Island,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Philipsburg Itinerary Caribbean
External from $4,487
price per person Taxes included
Wind Spirit | Feb 7, 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
Philipsburg Itinerary Caribbean
External from $3,694
price per person Taxes included
Wind Spirit | Feb 14, 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
sold out
Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $3,211
price per person Taxes included
Wind Spirit | Feb 14, 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
Philipsburg Itinerary Caribbean
External from $3,452
price per person Taxes included
Wind Spirit | Feb 21, 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, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $3,211
price per person Taxes included
Wind Spirit | Feb 21, 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
Philipsburg Itinerary Caribbean
External from $3,562
price per person Taxes included
Wind Surf | Feb 28, 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
sold out
Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Dominica, Sri Lanka, Barbados
Philipsburg Itinerary Caribbean
External from $3,042
price per person Taxes included
Wind Spirit | Feb 28, 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Bridgetown
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. St. John ,
5. Les Saintes,
6. Roseau,
7. Pigeon Island,
8. Bridgetown
Philipsburg Itinerary Caribbean
External from $3,525
price per person Taxes included
Wind Spirit | Feb 28, 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, Sri Lanka, Guadeloupe, Saint Barthelemy, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
External from $3,079
price per person Taxes included
Wind Surf | Feb 28, 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Pigeon Island,
5. Les Saintes,
6. Gustavia,
7. Basseterre,
8. Philipsburg
40 cruises