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Itineraries and cruises Windstar Cruises departing from Saint Johns

  • 2025
  • 2026
  • 2027
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January 2027
23 cruises

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

Saint Johns Itinerary Caribbean
from $3,683
price per person Taxes included
See the cruise Book
Star Pride | Oct. 26, 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 $4,317
price per person Taxes included
Star Pride | Oct. 26, 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, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands

Saint Johns Itinerary Caribbean
from $4,642
price per person Taxes included
See the cruise Book
Star Pride | Nov. 2, 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 $4,642
price per person Taxes included
Star Pride | Nov. 2, 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 $4,265
price per person Taxes included
See the cruise Book
Star Pride | Nov. 9, 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

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

Saint Johns Itinerary Caribbean
from $4,317
price per person Taxes included
Star Pride | Nov. 16, 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, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands

Saint Johns Itinerary Caribbean
from $4,317
price per person Taxes included
See the cruise Book
Star Pride | Nov. 16, 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 $4,265
price per person Taxes included
See the cruise Book
Star Pride | Nov. 23, 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 $4,317
price per person Taxes included
See the cruise Book
Star Pride | Nov. 30, 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 $4,317
price per person Taxes included
Star Pride | Nov. 30, 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, Dominican Republic, Spain, Panama

Saint Johns Itinerary Mediterranean
from $4,598
price per person Taxes included
Star Pride | Dec. 7, 2025
Duration: 6 nights
Departure from: Saint Johns Landing: Colon
Itinerary:
1. Saint Johns,
2. Santo Domingo,
3. navigation,
4. Cartagena ,
5. Cartagena ,
6. San Blas Island,
7. Colon

Mediterranean: Antigua and Barbuda, Dominican Republic, Spain, Panama

Saint Johns Itinerary Mediterranean
from $4,111
price per person Taxes included
See the cruise Book
Star Pride | Dec. 7, 2025
Duration: 6 nights
Departure from: Saint Johns Landing: Colon
Itinerary:
1. Saint Johns,
2. Santo Domingo,
3. navigation,
4. Cartagena ,
5. Cartagena ,
6. San Blas Island,
7. Colon

Caribbean: Antigua and Barbuda, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Guadeloupe, Sri Lanka, British Virgin Islands

Saint Johns Itinerary Caribbean
from $5,931
price per person Taxes included
See the cruise Book
Star Pride | Oct. 28, 2026
Duration: 11 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. St. John ,
3. Gustavia,
4. Basseterre,
5. navigation,
6. Les Saintes,
7. Pigeon Island,
8. Saint Johns,
9. navigation,
10. Jost Van Dyke,
11. Virgin Gorda,
12. Saint Johns

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

Saint Johns Itinerary Caribbean
from $4,103
price per person Taxes included
See the cruise Book
Star Pride | Nov. 8, 2026
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 Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands

Saint Johns Itinerary Caribbean
from $4,155
price per person Taxes included
See the cruise Book
Star Pride | Nov. 15, 2026
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 $4,103
price per person Taxes included
See the cruise Book
Star Pride | Nov. 22, 2026
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 $4,155
price per person Taxes included
See the cruise Book
Star Pride | Nov. 29, 2026
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

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

Saint Johns Itinerary Caribbean
from $4,103
price per person Taxes included
See the cruise Book
Star Pride | Dec. 6, 2026
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 $4,155
price per person Taxes included
See the cruise Book
Star Pride | Dec. 13, 2026
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

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

Saint Johns Itinerary Caribbean
from $4,428
price per person Taxes included
See the cruise Book
Star Pride | Dec. 20, 2026
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 $4,480
price per person Taxes included
See the cruise Book
Star Pride | Dec. 27, 2026
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

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

Saint Johns Itinerary Caribbean
from $4,103
price per person Taxes included
See the cruise Book
Star Pride | Jan. 3, 2027
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 Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands

Saint Johns Itinerary Caribbean
from $4,155
price per person Taxes included
See the cruise Book
Star Pride | Jan. 10, 2027
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
23 cruises