All Caribbean Cruises with Windstar Cruises in November 2025

  • 2026
  • 2027
12 cruises
sold out
Puerto Rico, Grenada, Saint Vincent and the Grenadines, Sri Lanka, Guadeloupe, Saint Martin
San Juan Itinerary Caribbean
Suite from $5,259
price per person Taxes included
Star Pride | 9/11/2025
Duration: 7 nights
Departure from: San Juan Landing: San Juan
Itinerary:
1. San Juan,
2. navigation,
3. Saint George,
4. Bequia,
5. Pigeon Island,
6. Les Saintes,
7. Marigot,
8. San Juan
sold out
Puerto Rico, Grenada, Saint Vincent and the Grenadines, Sri Lanka, Guadeloupe, Saint Martin
San Juan Itinerary Caribbean
Suite from $5,259
price per person Taxes included
Star Pride | 23/11/2025
Duration: 7 nights
Departure from: San Juan Landing: San Juan
Itinerary:
1. San Juan,
2. navigation,
3. Saint George,
4. Bequia,
5. Pigeon Island,
6. Les Saintes,
7. Marigot,
8. San Juan
sold out
Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from $5,323
price per person Taxes included
Star Pride | 16/11/2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
sold out
Antigua and Barbuda, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from $5,323
price per person Taxes included
Star Pride | 30/11/2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Gustavia,
4. Basseterre,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Saint Johns Itinerary Caribbean
Suite from $5,459
price per person Taxes included
Star Pride | 9/11/2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns
Saint Johns Itinerary Caribbean
Suite from $5,523
price per person Taxes included
Star Pride | 16/11/2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
sold out
Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from $5,723
price per person Taxes included
Star Pride | 2/11/2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Saint Johns Itinerary Caribbean
Suite from $5,723
price per person Taxes included
Star Pride | 30/11/2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Gustavia,
4. Basseterre,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Saint Johns Itinerary Caribbean
Suite from $5,859
price per person Taxes included
Star Pride | 23/11/2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns
Saint Johns Itinerary Caribbean
Suite from $5,923
price per person Taxes included
Star Pride | 2/11/2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
sold out
Barbados, Saint Vincent and the Grenadines, Grenada, Netherlands Antilles, Aruba, Spain, Panama
Bridgetown Itinerary Caribbean
External from $7,680
price per person Taxes included
Wind Spirit | 18/11/2025
Duration: 11 nights
Departure from: Bridgetown Landing: Colon
Itinerary:
1. Bridgetown,
2. Bequia,
3. Mayreau,
4. Saint George,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad,
9. navigation,
10. Cartagena ,
11. navigation,
12. Colon
Bridgetown Itinerary Caribbean
External from $9,280
price per person Taxes included
Wind Spirit | 18/11/2025
Duration: 11 nights
Departure from: Bridgetown Landing: Colon
Itinerary:
1. Bridgetown,
2. Bequia,
3. Mayreau,
4. Saint George,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad,
9. navigation,
10. Cartagena ,
11. navigation,
12. Colon
12 cruises