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home › Cruise lines›Windstar Cruises› Cruises Wind Surf›January 2026

Cruises Wind Surf January 2026

  • 2025
  • 2026
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7 cruises
sold out

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

Philipsburg Itinerary Caribbean
from $4,785
price per person Taxes included
Wind Surf | 4 Jan 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

Caribbean: Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Saint Vincent and the Grenadines, Barbados

Philipsburg Itinerary Caribbean
from $5,016
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 11 Jan 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, Saint Barthelemy, Virgin Islands, Guadeloupe, Sri Lanka, Saint Vincent and the Grenadines, Barbados

Philipsburg Itinerary Caribbean
from $4,832
price per person Taxes included
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: Barbados, Martinique, Saint Lucia, Sri Lanka, Saint Vincent and the Grenadines, Antigua and Barbuda

Bridgetown Itinerary Caribbean
from $4,990
price per person Taxes included
See the cruise Book Online Book Online
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 Johns,
9. Bridgetown
sold out

Barbados, Martinique, Saint Lucia, Sri Lanka, Saint Vincent and the Grenadines, Antigua and Barbuda

Bridgetown Itinerary Caribbean
from $4,990
price per person Taxes included
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 Johns,
9. Bridgetown

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

Bridgetown Itinerary Caribbean
from $5,544
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 25 Jan 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Oranjestad
Itinerary:
1. Bridgetown,
2. Bequia,
3. Mayreau,
4. Soufriere,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad
sold out

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

Bridgetown Itinerary Caribbean
from $5,177
price per person Taxes included
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
7 cruises