All Caribbean Cruises with Windstar Cruises in December 2026

  • 2025
  • 2027
14 cruises
Saint Johns Itinerary Caribbean
Suite from £2,781
price per person Taxes included
Star Pride | 6 Dec 2026
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns
Saint Johns Itinerary Caribbean
Suite from £2,809
price per person Taxes included
Star Pride | 13 Dec 2026
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Gustavia,
4. Basseterre,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Saint Johns Itinerary Caribbean
Suite from £2,958
price per person Taxes included
Star Pride | 20 Dec 2026
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns
Philipsburg Itinerary Caribbean
External from £2,977
price per person Taxes included
Wind Surf | 26 Dec 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
Philipsburg Itinerary Caribbean
External from £2,991
price per person Taxes included
Wind Surf | 19 Dec 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
Bridgetown Itinerary Caribbean
Suite from £3,126
price per person Taxes included
Star Legend | 4 Dec 2026
Duration: 8 nights
Departure from: Bridgetown Landing: Oranjestad
Itinerary:
1. Bridgetown,
2. Rodney Bay,
3. Pitons,
4. Scarborough,
5. Bequia,
6. Mayreau,
7. navigation,
8. Kralendijk,
9. Willemstad,
10. Oranjestad
Saint Johns Itinerary Caribbean
Suite from £3,786
price per person Taxes included
Star Pride | 27 Dec 2026
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Gustavia,
4. Basseterre,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Saint Johns Itinerary Caribbean
Suite from £4,436
price per person Taxes included
Star Pride | 6 Dec 2026
Duration: 14 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns,
9. St. John ,
10. Gustavia,
11. Basseterre,
12. Philipsburg,
13. Jost Van Dyke,
14. Virgin Gorda,
15. Saint Johns
Philipsburg Itinerary Caribbean
External from £4,459
price per person Taxes included
Wind Surf | 26 Dec 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
Saint Johns Itinerary Caribbean
Suite from £4,613
price per person Taxes included
Star Pride | 13 Dec 2026
Duration: 14 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Gustavia,
4. Basseterre,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns,
9. navigation,
10. Saint George,
11. Bequia,
12. Mayreau,
13. Les Saintes,
14. Marigot,
15. Saint Johns
14 cruises