All Caribbean Cruises with Windstar Cruises in January 2026

  • 2024
  • 2025
  • 2026
7 cruises

Caribbean: Sint Maarten, Antigua and Barbuda, United Kingdom, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 51 284,41
price per person Taxes included
16 reservations in 36 hours
Wind Surf | 04 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Falmouth Harbour,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg

Caribbean: Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Sri Lanka, Saint Vincent and the Grenadines, Barbados

Philipsburg Itinerary Caribbean
from R 51 795,29
price per person Taxes included
18 reservations in 36 hours
Wind Surf | 11 Jan 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

Caribbean: Sint Maarten, Saint Kitts and Nevis, Dominica, Saint Lucia, Martinique, Guadeloupe, United States, British Virgin Islands, Virgin Islands, Saint Barthelemy

Philipsburg Itinerary Caribbean
from R 71 385,54
price per person Taxes included
19 reservations in 36 hours
Wind Spirit | 14 Jan 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

Caribbean: Barbados, Martinique, Saint Lucia, Sri Lanka, Saint Vincent and the Grenadines, Grenada

Bridgetown Itinerary Caribbean
from R 53 485,12
price per person Taxes included
16 reservations in 36 hours
Wind Surf | 18 Jan 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Fort de france,
3. Castries,
4. Pigeon Island,
5. Pigeon Island,
6. Bequia,
7. Mayreau,
8. Saint George,
9. Bridgetown

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

Philipsburg Itinerary Caribbean
from R 52 266,87
price per person Taxes included
19 reservations in 36 hours
Wind Spirit | 24 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. St. John ,
3. Anguilla,
4. Virgin Gorda,
5. Tortola Island,
6. Tortola Island,
7. Jost Van Dyke,
8. Gustavia,
9. Philipsburg

Caribbean: Barbados, United Kingdom, Saint Vincent and the Grenadines, Saint Lucia, Netherlands Antilles, Aruba

Bridgetown Itinerary Caribbean
from R 55 489,34
price per person Taxes included
19 reservations in 48 hours
Wind Surf | 25 Jan 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Oranjestad
Itinerary:
1. Bridgetown,
2. Man of War Bay,
3. Mayreau,
4. Soufriere,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad

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

Philipsburg Itinerary Caribbean
from R 50 301,95
price per person Taxes included
21 reservations in 36 hours
Wind Spirit | 31 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. St. John ,
3. Anguilla,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
7 cruises