Windstar Cruises from Caribbean: Departures October 2026 $2,739

2 cruises

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Suite from $4,821
price per person Taxes included

Star Pride | Oct. 20, 2026

Duration: 8 nights

Departure from: Boston Landing: Saint Johns

Itinerary:

1. Boston,

2. navigation,

3. navigation,

4. Hamilton,

5. Hamilton,

6. Saint George,

7. Saint George,

8. navigation,

9. navigation,

10. Saint Johns

Suite from $7,013
price per person Taxes included

Star Pride | Oct. 28, 2026

Duration: 11 nights

Departure from: Saint Johns Landing: Saint Johns

Itinerary:

1. Saint Johns,

2. St. John ,

3. Gustavia,

4. Basseterre,

5. navigation,

6. Les Saintes,

7. Pigeon Island,

8. Saint George,

9. navigation,

10. Jost Van Dyke,

11. Virgin Gorda,

12. Saint Johns

2 cruises

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All Caribbean Cruises with Windstar Cruises in October 2026