Windstar Cruises from Caribbean: Departures January 2026 $1,969

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

External from $6,119
price per person Taxes included

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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, Dominica, Saint Vincent and the Grenadines, Barbados

External from $6,167
price per person Taxes included

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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

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

External from $6,326
price per person Taxes included

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

External from $6,699
price per person Taxes included

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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

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

External from $7,136
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

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

External from $7,321
price per person Taxes included

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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

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

External from $7,432
price per person Taxes included

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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. Charlestown,

6. Basseterre,

7. Saint Johns,

8. navigation,

9. Gustavia,

10. Tortola Island,

11. Philipsburg

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

External from $10,783
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

All Caribbean Cruises with Windstar Cruises in January 2026