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

External from $5,527
price per person Taxes included

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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

External from $4,218
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, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $4,380
price per person Taxes included

See the cruise Book

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

External from $4,422
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

External from $4,260
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

External from $5,871
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

External from $7,002
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

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

External from $4,399
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 George,

9. Bridgetown

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

External from $4,399
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 George,

9. Bridgetown

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

External from $4,460
price per person Taxes included

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

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

External from $4,299
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: Barbados, Saint Vincent and the Grenadines, Saint Lucia, Netherlands Antilles, Aruba

External from $4,887
price per person Taxes included

See the cruise Book

Wind Surf | Jan. 25, 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

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

External from $4,564
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

External from $4,137
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

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

External from $4,137
price per person Taxes included

See the cruise Book

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