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

External from $3,475
price per person Taxes included

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Wind Surf | Dec. 2, 2025

Duration: 5 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Tortola Island,

3. Jost Van Dyke,

4. Jost Van Dyke,

5. Virgin Gorda,

6. Gustavia,

7. Philipsburg

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

External from $3,313
price per person Taxes included

Wind Surf | Dec. 2, 2025

Duration: 5 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Tortola Island,

3. Jost Van Dyke,

4. Jost Van Dyke,

5. Virgin Gorda,

6. Gustavia,

7. Philipsburg

Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

External from $3,799
price per person Taxes included

Wind Surf | Dec. 7, 2025

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Roseau,

4. Mayreau,

5. Les Saintes,

6. Basseterre,

7. Gustavia,

8. Philipsburg

Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

External from $4,123
price per person Taxes included

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Wind Surf | Dec. 7, 2025

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Roseau,

4. Mayreau,

5. Les Saintes,

6. Basseterre,

7. Gustavia,

8. Philipsburg

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

External from $3,987
price per person Taxes included

Wind Surf | Dec. 14, 2025

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 $4,310
price per person Taxes included

See the cruise Book

Wind Surf | Dec. 14, 2025

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

External from $4,890
price per person Taxes included

See the cruise Book

Wind Spirit | Dec. 20, 2025

Duration: 8 nights

Departure from: Oranjestad Landing: Bridgetown

Itinerary:

1. Oranjestad,

2. Willemstad,

3. Kralendijk,

4. navigation,

5. Saint George,

6. Saint George,

7. Mayreau,

8. Bequia,

9. Bridgetown

Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

External from $4,931
price per person Taxes included

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Wind Surf | Dec. 21, 2025

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Roseau,

4. Mayreau,

5. Les Saintes,

6. Basseterre,

7. Gustavia,

8. Philipsburg

Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy

External from $4,446
price per person Taxes included

Wind Surf | Dec. 21, 2025

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Roseau,

4. Mayreau,

5. Les Saintes,

6. Basseterre,

7. Gustavia,

8. Philipsburg

Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Sri Lanka, Martinique

External from $4,712
price per person Taxes included

Wind Spirit | Dec. 28, 2025

Duration: 7 nights

Departure from: Bridgetown Landing: Bridgetown

Itinerary:

1. Bridgetown,

2. navigation,

3. Basseterre,

4. Les Saintes,

5. Roseau,

6. Pigeon Island,

7. Fort de france,

8. Bridgetown

Caribbean: Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Martinique

External from $5,197
price per person Taxes included

See the cruise Book

Wind Spirit | Dec. 28, 2025

Duration: 7 nights

Departure from: Bridgetown Landing: Bridgetown

Itinerary:

1. Bridgetown,

2. navigation,

3. Basseterre,

4. Les Saintes,

5. Roseau,

6. Mayreau,

7. Fort de france,

8. Bridgetown

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

External from $5,118
price per person Taxes included

See the cruise Book

Wind Surf | Dec. 28, 2025

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

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

External from $4,472
price per person Taxes included

Wind Surf | Dec. 28, 2025

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

All Caribbean Cruises with Windstar Cruises in December 2025