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All Caribbean Cruises with Windstar Cruises in December 2025

  • 2026
  • 2027
October 2025 November 2025 December 2025
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January 2027 February 2027 March 2027
13 cruises
sold out
Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from £1,821
price per person Taxes included
Wind Surf | 2 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, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from £2,089
price per person Taxes included
Wind Surf | 7 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
Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from £2,177
price per person Taxes included
See the cruise Book
Wind Surf | 2 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
External from £2,192
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: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from £2,266
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 7 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
External from £2,444
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
Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from £2,458
price per person Taxes included
See the cruise Book Online Book Online
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
sold out
Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from £2,458
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
sold out
Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Sri Lanka, Martinique
Bridgetown Itinerary Caribbean
External from £2,591
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: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from £2,888
price per person Taxes included
See the cruise Book Online Book Online
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
Caribbean: Aruba, Netherlands Antilles, Grenada, Saint Vincent and the Grenadines, Barbados
Oranjestad Itinerary Caribbean
External from £2,955
price per person Taxes included
See the cruise Book Online Book Online
Wind Spirit | 20 Dec 2025
Duration: 8 nights
Departure from: Oranjestad Landing: Bridgetown
Itinerary:
1. Oranjestad,
2. Willemstad,
3. Kralendijk,
4. navigation,
5. Saint George,
6. Saint George,
7. Mayreau,
8. Bequia,
9. Bridgetown
Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from £3,080
price per person Taxes included
See the cruise Book Online Book Online
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
Caribbean: Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Saint Vincent and the Grenadines
Bridgetown Itinerary Caribbean
External from £3,124
price per person Taxes included
See the cruise Book Online Book Online
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. Bridgetown
13 cruises