All Caribbean Cruises with Windstar Cruises in December 2025

  • 2025
  • 2026
  • 2027
11 cruises

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

Philipsburg Itinerary Caribbean
from R 46 679
price per person Taxes included
Wind Surf | 02 Dec 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
sold out

Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 44 508
price per person Taxes included
Wind Surf | 02 Dec 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

Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 51 043
price per person Taxes included
Wind Surf | 07 Dec 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
from R 51 043
price per person Taxes included
Wind Surf | 07 Dec 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, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 53 562
price per person Taxes included
Wind Surf | 14 Dec 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

Caribbean: Aruba, Netherlands Antilles, Antigua and Barbuda, Saint Vincent and the Grenadines, Barbados

Oranjestad Itinerary Caribbean
from R 63 527
price per person Taxes included
4 reservations in 72 hours
Wind Spirit | 20 Dec 2025
Duration: 8 nights
Departure from: Oranjestad Landing: Bridgetown
Itinerary:
1. Oranjestad,
2. Willemstad,
3. Kralendijk,
4. navigation,
5. Saint Johns,
6. Saint Johns,
7. Mayreau,
8. Bequia,
9. Bridgetown

Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 64 070
price per person Taxes included
Wind Surf | 21 Dec 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
from R 59 728
price per person Taxes included
Wind Surf | 21 Dec 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

Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Sri Lanka, Martinique

Bridgetown Itinerary Caribbean
from R 63 310
price per person Taxes included
Wind Spirit | 28 Dec 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Pigeon Island,
7. Fort de france,
8. Bridgetown

Caribbean: Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Martinique

Bridgetown Itinerary Caribbean
from R 67 652
price per person Taxes included
Wind Spirit | 28 Dec 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Mayreau,
7. Fort de france,
8. Bridgetown
sold out

Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 60 075
price per person Taxes included
Wind Surf | 28 Dec 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
11 cruises