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All Caribbean Cruises with Windstar Cruises in November 2025

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6 cruises

Caribbean: Puerto Rico, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, Virgin Islands, British Virgin Islands

San Juan Itinerary Caribbean
from $4,734.70
price per person Taxes included
8 reservations in 48 hours
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Star Pride | 2 Nov 2025
Duration: 7 nights
Departure from: San Juan Landing: San Juan
Itinerary:
1. San Juan,
2. navigation,
3. Basseterre,
4. Gustavia,
5. Sint Maarten,
6. Jost Van Dyke,
7. Virgin Gorda,
8. San Juan

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

San Juan Itinerary Caribbean
from $4,903.86
price per person Taxes included
11 reservations in 48 hours
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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: Puerto Rico, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, Virgin Islands, British Virgin Islands

San Juan Itinerary Caribbean
from $4,734.70
price per person Taxes included
8 reservations in 36 hours
See the cruise
Star Pride | 16 Nov 2025
Duration: 7 nights
Departure from: San Juan Landing: San Juan
Itinerary:
1. San Juan,
2. navigation,
3. Basseterre,
4. Gustavia,
5. Sint Maarten,
6. Jost Van Dyke,
7. Virgin Gorda,
8. San Juan

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

Bridgetown Itinerary Caribbean
from $5,918.80
price per person Taxes included
19 reservations in 36 hours
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Wind Spirit | 18 Nov 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

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

San Juan Itinerary Caribbean
from $4,903.86
price per person Taxes included
12 reservations in 48 hours
See the cruise
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: Puerto Rico, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, Virgin Islands, British Virgin Islands

San Juan Itinerary Caribbean
from $4,734.70
price per person Taxes included
9 reservations in 36 hours
See the cruise
Star Pride | 30 Nov 2025
Duration: 7 nights
Departure from: San Juan Landing: San Juan
Itinerary:
1. San Juan,
2. navigation,
3. Gustavia,
4. Basseterre,
5. Sint Maarten,
6. Jost Van Dyke,
7. Virgin Gorda,
8. San Juan
6 cruises