Windstar Cruises from Philipsburg: 63 Departures

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

External from $5,115
price per person Taxes included

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Wind Surf | 3 Jan 2028

Duration: 6 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Tortola Island,

3. Gustavia,

4. Jost Van Dyke,

5. Virgin Gorda,

6. Tortola Island,

7. Philipsburg

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

External from $5,270
price per person Taxes included

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Wind Surf | 28 Nov 2027

Duration: 7 nights

Departure from: Philipsburg Landing: Philipsburg

Itinerary:

1. Philipsburg,

2. Charlestown,

3. Roseau,

4. Mayreau,

5. Les Saintes,

6. Gustavia,

7. Basseterre,

8. Philipsburg

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

External from $5,270
price per person Taxes included

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Wind Surf | 12 Dec 2027

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, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $5,300
price per person Taxes included

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Wind Surf | 5 Dec 2027

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 $5,485
price per person Taxes included

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Wind Surf | 27 Feb 2028

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

External from $5,485
price per person Taxes included

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Wind Surf | 13 Feb 2028

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, British Virgin Islands, Virgin Islands, Saint Barthelemy

External from $5,485
price per person Taxes included

See the cruise Book

Wind Surf | 30 Jan 2028

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

External from $5,485
price per person Taxes included

See the cruise Book

Wind Surf | 16 Jan 2028

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 $5,485
price per person Taxes included

See the cruise Book

Wind Surf | 12 Mar 2028

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

External from $5,640
price per person Taxes included

See the cruise Book

Wind Surf | 6 Feb 2028

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

Itineraries and cruises Windstar Cruises departing from Philipsburg