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All Caribbean Cruises with Windstar Cruises in November 2025

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January 2027
12 cruises

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

Saint Johns Itinerary Caribbean
from $5,335
price per person Taxes included
5 reservations in 72 hours
See the cruise Book
Star Pride | 2 Nov 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
from $5,335
price per person Taxes included
Star Pride | 2 Nov 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

Caribbean: Antigua and Barbuda, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin

Saint Johns Itinerary Caribbean
from $4,903
price per person Taxes included
See the cruise Book
Star Pride | 9 Nov 2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint Johns,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns
sold out

Puerto Rico, Grenada, Saint Vincent and the Grenadines, Sri Lanka, Guadeloupe, Saint Martin

San Juan Itinerary Caribbean
from $4,903
price per person Taxes included
Star Pride | 9 Nov 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

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

Saint Johns Itinerary Caribbean
from $4,962
price per person Taxes included
See the cruise Book
Star Pride | 16 Nov 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
from $4,962
price per person Taxes included
Star Pride | 16 Nov 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

Caribbean: Barbados, Saint Vincent and the Grenadines, Antigua and Barbuda, Netherlands Antilles, Aruba, Spain, Panama

Bridgetown Itinerary Caribbean
from $7,906
price per person Taxes included
See the cruise Book
Wind Spirit | 18 Nov 2025
Duration: 11 nights
Departure from: Bridgetown Landing: Colon
Itinerary:
1. Bridgetown,
2. Bequia,
3. Mayreau,
4. Saint Johns,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad,
9. navigation,
10. Cartagena ,
11. navigation,
12. Colon
sold out

Barbados, Saint Vincent and the Grenadines, Antigua and Barbuda, Netherlands Antilles, Aruba, Spain, Panama

Bridgetown Itinerary Caribbean
from $7,160
price per person Taxes included
Wind Spirit | 18 Nov 2025
Duration: 11 nights
Departure from: Bridgetown Landing: Colon
Itinerary:
1. Bridgetown,
2. Bequia,
3. Mayreau,
4. Saint Johns,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad,
9. navigation,
10. Cartagena ,
11. navigation,
12. Colon
sold out

Puerto Rico, Grenada, Saint Vincent and the Grenadines, Sri Lanka, Guadeloupe, Saint Martin

San Juan Itinerary Caribbean
from $4,903
price per person Taxes included
Star Pride | 23 Nov 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

Caribbean: Antigua and Barbuda, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin

Saint Johns Itinerary Caribbean
from $4,903
price per person Taxes included
1 booking in 72 hours
See the cruise Book
Star Pride | 23 Nov 2025
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint Johns,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns

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

Saint Johns Itinerary Caribbean
from $4,962
price per person Taxes included
See the cruise Book
Star Pride | 30 Nov 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
sold out

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

Saint Johns Itinerary Caribbean
from $4,962
price per person Taxes included
Star Pride | 30 Nov 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
12 cruises