All Caribbean Cruises with Windstar Cruises in January 2026

15 cruises
sold out
Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $4,733
price per person Taxes included
Wind Spirit | 31 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Saint Johns,
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 $4,825
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
sold out
Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Sri Lanka, Saint Vincent and the Grenadines, Barbados
Philipsburg Itinerary Caribbean
External from $4,873
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
sold out
Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $4,917
price per person Taxes included
Wind Spirit | 24 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Saint Johns,
3. Tortola Island,
4. Virgin Gorda,
5. Tortola Island,
6. Tortola Island,
7. Jost Van Dyke,
8. Gustavia,
9. Philipsburg
sold out
Barbados, Martinique, Saint Lucia, Sri Lanka, Saint Vincent and the Grenadines, Grenada
Bridgetown Itinerary Caribbean
External from $5,032
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 George,
9. Bridgetown
sold out
Barbados, United Kingdom, Saint Vincent and the Grenadines, Saint Lucia, Netherlands Antilles, Aruba
Bridgetown Itinerary Caribbean
External from $5,221
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
Philipsburg Itinerary Caribbean
External from $5,982
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. Saint Johns,
5. Les Saintes,
6. Roseau,
7. Mayreau,
8. Bridgetown
Philipsburg Itinerary Caribbean
External from $6,119
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
Bridgetown Itinerary Caribbean
External from $6,145
price per person Taxes included
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
Bridgetown Itinerary Caribbean
External from $6,511
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 George,
9. Bridgetown
Philipsburg Itinerary Caribbean
External from $6,581
price per person Taxes included
Wind Spirit | 24 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Saint Johns,
3. Tortola Island,
4. Virgin Gorda,
5. Tortola Island,
6. Tortola Island,
7. Jost Van Dyke,
8. Gustavia,
9. Philipsburg
Bridgetown Itinerary Caribbean
External from $6,692
price per person Taxes included
Wind Spirit | 4 Jan 2026
Duration: 10 nights
Departure from: Bridgetown Landing: Philipsburg
Itinerary:
1. Bridgetown,
2. Mayreau,
3. Roseau,
4. Fort de france,
5. Deshaies,
6. Basseterre,
7. Saint Johns,
8. navigation,
9. Gustavia,
10. Tortola Island,
11. Philipsburg
sold out
Sint Maarten, Saint Kitts and Nevis, Dominica, Saint Lucia, Martinique, Guadeloupe, United States, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $6,716
price per person Taxes included
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
Philipsburg Itinerary Caribbean
External from $6,951
price per person Taxes included
Wind Spirit | 31 Jan 2026
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Saint Johns,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
Philipsburg Itinerary Caribbean
External from $9,859
price per person Taxes included
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
15 cruises