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Itineraries and cruises Windstar Cruises departing from San Juan

  • 2024
  • 2025
November 2024 December 2024
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13 cruises

Caribbean: Puerto Rico, Sint Maarten, United States, Saint Barthelemy, Virgin Islands, British Virgin Islands

San Juan Itinerary Caribbean
from TRY 89,325.76
price per person Taxes included
13 reservations in 48 hours
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Star Pride | Nov 3, 2024
Duration: 6 nights
Departure from: San Juan Landing: San Juan
Itinerary:
1. San Juan,
2. Sint Maarten,
3. Charlestown,
4. Gustavia,
5. Jost Van Dyke,
6. Virgin Gorda,
7. San Juan

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

San Juan Itinerary Caribbean
from TRY 103,623.60
price per person Taxes included
13 reservations in 48 hours
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Star Pride | Nov 9, 2024
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. Sint Maarten,
8. San Juan

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

San Juan Itinerary Caribbean
from TRY 89,325.76
price per person Taxes included
10 reservations in 48 hours
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Star Pride | Nov 16, 2024
Duration: 7 nights
Departure from: San Juan Landing: San Juan
Itinerary:
1. San Juan,
2. Saint Thomas,
3. Sint Maarten,
4. Gustavia,
5. Basseterre,
6. Jost Van Dyke,
7. Virgin Gorda,
8. San Juan

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

San Juan Itinerary Caribbean
from TRY 89,325.76
price per person Taxes included
13 reservations in 48 hours
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Star Pride | Nov 23, 2024
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. Sint Maarten,
8. San Juan

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

San Juan Itinerary Caribbean
from TRY 92,900.22
price per person Taxes included
10 reservations in 36 hours
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Star Pride | Nov 30, 2024
Duration: 7 nights
Departure from: San Juan Landing: San Juan
Itinerary:
1. San Juan,
2. Saint Thomas,
3. Sint Maarten,
4. Basseterre,
5. Gustavia,
6. Jost Van Dyke,
7. Virgin Gorda,
8. San Juan

Caribbean: Puerto Rico, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Dominica, Sri Lanka, Grenada, Barbados

San Juan Itinerary Caribbean
from TRY 89,325.76
price per person Taxes included
13 reservations in 48 hours
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Star Pride | Dec 7, 2024
Duration: 7 nights
Departure from: San Juan Landing: Bridgetown
Itinerary:
1. San Juan,
2. Saint Thomas,
3. Gustavia,
4. Basseterre,
5. Roseau,
6. Pigeon Island,
7. Saint George,
8. Bridgetown

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

San Juan Itinerary Caribbean
from TRY 100,049.14
price per person Taxes included
9 reservations in 48 hours
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Star Pride | Oct 26, 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, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, Virgin Islands, British Virgin Islands

San Juan Itinerary Caribbean
from TRY 100,049.14
price per person Taxes included
8 reservations in 48 hours
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Star Pride | Nov 2, 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 TRY 103,623.60
price per person Taxes included
11 reservations in 48 hours
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Star Pride | Nov 9, 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 TRY 100,049.14
price per person Taxes included
8 reservations in 36 hours
See the cruise
Star Pride | Nov 16, 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 TRY 103,623.60
price per person Taxes included
12 reservations in 48 hours
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Star Pride | Nov 23, 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 TRY 100,049.14
price per person Taxes included
9 reservations in 36 hours
See the cruise
Star Pride | Nov 30, 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

Mediterranean: Puerto Rico, Dominican Republic, Spain, Panama

San Juan Itinerary Mediterranean
from TRY 100,049.14
price per person Taxes included
12 reservations in 36 hours
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Star Pride | Dec 7, 2025
Duration: 6 nights
Departure from: San Juan Landing: Colon
Itinerary:
1. San Juan,
2. Santo Domingo,
3. navigation,
4. Cartagena ,
5. Cartagena ,
6. San Blas Island,
7. Colon
13 cruises