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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 $3,729.68
price per person Taxes included
13 reservations in 48 hours
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Star Pride | 3 Nov 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 $4,326.67
price per person Taxes included
13 reservations in 48 hours
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Star Pride | 9 Nov 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 $3,729.68
price per person Taxes included
10 reservations in 48 hours
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Star Pride | 16 Nov 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 $3,729.68
price per person Taxes included
13 reservations in 48 hours
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Star Pride | 23 Nov 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 $3,878.93
price per person Taxes included
10 reservations in 36 hours
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Star Pride | 30 Nov 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 $3,729.68
price per person Taxes included
13 reservations in 48 hours
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Star Pride | 7 Dec 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 $4,177.42
price per person Taxes included
9 reservations in 48 hours
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Star Pride | 26 Oct 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 $4,177.42
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 $4,326.67
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 $4,177.42
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: Puerto Rico, Grenada, Saint Vincent and the Grenadines, Sri Lanka, Guadeloupe, Saint Martin

San Juan Itinerary Caribbean
from $4,326.67
price per person Taxes included
12 reservations in 48 hours
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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 $4,177.42
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

Mediterranean: Puerto Rico, Dominican Republic, Spain, Panama

San Juan Itinerary Mediterranean
from $4,177.42
price per person Taxes included
12 reservations in 36 hours
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Star Pride | 7 Dec 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