Caribbean: Barbados, Saint Vincent and the Grenadines, Dominica, Martinique, France, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy, British Virgin Islands, Sint Maarten

from $3,895
price per person Taxes included

See the cruise Book

Wind Spirit | Jan 4, 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

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

from $2,972
price per person Taxes included

Wind Surf | Jan 4, 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

from $3,002
price per person Taxes included

See the cruise Book

Wind Surf | Jan 11, 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

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

from $3,002
price per person Taxes included

Wind Surf | Jan 11, 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

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

from $4,138
price per person Taxes included

Wind Spirit | Jan 14, 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: Sint Maarten, Saint Kitts and Nevis, Dominica, Saint Lucia, Martinique, Guadeloupe, United States, British Virgin Islands, Virgin Islands, Saint Barthelemy

from $5,162
price per person Taxes included

See the cruise Book

Wind Spirit | Jan 14, 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, Antigua and Barbuda

from $3,100
price per person Taxes included

See the cruise Book

Wind Surf | Jan 18, 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

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

from $3,100
price per person Taxes included

Wind Surf | Jan 18, 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

Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy

from $3,029
price per person Taxes included

Wind Spirit | Jan 24, 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

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

from $3,143
price per person Taxes included

4 reservations in 72 hours

See the cruise Book

Wind Spirit | Jan 24, 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

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

from $3,444
price per person Taxes included

4 reservations in 72 hours

See the cruise Book

Wind Surf | Jan 25, 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

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

from $3,216
price per person Taxes included

Wind Surf | Jan 25, 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

Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy

from $2,916
price per person Taxes included

Wind Spirit | Jan 31, 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

All Caribbean Cruises with Windstar Cruises in January 2026

Caribbean: Barbados, Saint Vincent and the Grenadines, Dominica, Martinique, France, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy, British Virgin Islands, Sint Maarten

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

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

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

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

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

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

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

Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy

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

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

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

Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy