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Itineraries and cruises Windstar Cruises departing from Bridgetown

  • 2025
  • 2026
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31 cruises
sold out

Barbados, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, Grenada

Bridgetown Itinerary Caribbean
from $3,456
price per person Taxes included
Wind Spirit | Feb 15, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Pigeon Island,
3. Pigeon Island,
4. Castries,
5. Pitons,
6. Kingstown,
7. Mayreau,
8. Saint George,
9. Bequia,
10. Bridgetown
sold out

Barbados, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, Grenada

Bridgetown Itinerary Caribbean
from $3,987
price per person Taxes included
Wind Spirit | Feb 15, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Pigeon Island,
3. Pigeon Island,
4. Castries,
5. Pitons,
6. Kingstown,
7. Mayreau,
8. Saint George,
9. Bequia,
10. Bridgetown
sold out

Barbados, Portugal

Bridgetown Itinerary Ocean Cruises
from $2,578
price per person Taxes included
Wind Spirit | Feb 22, 2025
Duration: 15 nights
Departure from: Bridgetown Landing: Lisbon
Itinerary:
1. Bridgetown,
2. navigation,
3. navigation,
4. navigation,
5. navigation,
6. navigation,
7. navigation,
8. navigation,
9. navigation,
10. navigation,
11. navigation,
12. navigation,
13. navigation,
14. navigation,
15. navigation,
16. Lisbon

Ocean Cruises: Barbados, Portugal

Bridgetown Itinerary Ocean Cruises
from $2,322
price per person Taxes included
Wind Spirit | Feb 22, 2025
Duration: 15 nights
Departure from: Bridgetown Landing: Lisbon
Itinerary:
1. Bridgetown,
2. navigation,
3. navigation,
4. navigation,
5. navigation,
6. navigation,
7. navigation,
8. navigation,
9. navigation,
10. navigation,
11. navigation,
12. navigation,
13. navigation,
14. navigation,
15. navigation,
16. Lisbon

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

Bridgetown Itinerary Caribbean
from $5,335
price per person Taxes included
Star Pride | Feb 22, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Oranjestad
Itinerary:
1. Bridgetown,
2. Mayreau,
3. Soufriere,
4. Saint George,
5. navigation,
6. Willemstad,
7. Oranjestad
sold out

Barbados, United Kingdom, Saint Vincent and the Grenadines, Saint Lucia, Grenada, Netherlands Antilles, Aruba

Bridgetown Itinerary Caribbean
from $3,528
price per person Taxes included
Star Pride | Feb 22, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Oranjestad
Itinerary:
1. Bridgetown,
2. Man of War Bay,
3. Mayreau,
4. Soufriere,
5. Saint George,
6. navigation,
7. Willemstad,
8. Oranjestad

Ocean Cruises: Barbados, Portugal

Bridgetown Itinerary Ocean Cruises
from $2,704
price per person Taxes included
Wind Star | Mar 26, 2025
Duration: 15 nights
Departure from: Bridgetown Landing: Lisbon
Itinerary:
1. Bridgetown,
2. navigation,
3. navigation,
4. navigation,
5. navigation,
6. navigation,
7. navigation,
8. navigation,
9. navigation,
10. navigation,
11. navigation,
12. navigation,
13. navigation,
14. navigation,
15. navigation,
16. Lisbon
sold out

Barbados, Portugal

Bridgetown Itinerary Ocean Cruises
from $2,578
price per person Taxes included
Wind Star | Mar 26, 2025
Duration: 15 nights
Departure from: Bridgetown Landing: Lisbon
Itinerary:
1. Bridgetown,
2. navigation,
3. navigation,
4. navigation,
5. navigation,
6. navigation,
7. navigation,
8. navigation,
9. navigation,
10. navigation,
11. navigation,
12. navigation,
13. navigation,
14. navigation,
15. navigation,
16. Lisbon
sold out

Barbados, Sri Lanka, Saint Lucia, Martinique, Saint Vincent and the Grenadines, Grenada

Bridgetown Itinerary Caribbean
from $2,804
price per person Taxes included
Star Pride | Mar 29, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Pigeon Island,
3. Pigeon Island,
4. Castries,
5. Pitons,
6. Fort de france,
7. Mayreau,
8. Saint George,
9. Bequia,
10. Bridgetown

Caribbean: Barbados, Sri Lanka, Saint Lucia, Martinique, Saint Vincent and the Grenadines, Grenada

Bridgetown Itinerary Caribbean
from $2,388
price per person Taxes included
2 reservations in 72 hours
Star Pride | Mar 29, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Pigeon Island,
3. Pigeon Island,
4. Castries,
5. Pitons,
6. Fort de france,
7. Mayreau,
8. Saint George,
9. Bequia,
10. Bridgetown

Ocean Cruises: Barbados, Spain

Bridgetown Itinerary Ocean Cruises
from $2,172
price per person Taxes included
Star Pride | Apr 5, 2025
Duration: 10 nights
Departure from: Bridgetown Landing: Santa Cruz de Tenerife
Itinerary:
1. Bridgetown,
2. navigation,
3. navigation,
4. navigation,
5. navigation,
6. navigation,
7. navigation,
8. navigation,
9. navigation,
10. navigation,
11. Santa Cruz de Tenerife
sold out

Barbados, Spain

Bridgetown Itinerary Ocean Cruises
from $2,555
price per person Taxes included
Star Pride | Apr 5, 2025
Duration: 10 nights
Departure from: Bridgetown Landing: Santa Cruz de Tenerife
Itinerary:
1. Bridgetown,
2. navigation,
3. navigation,
4. navigation,
5. navigation,
6. navigation,
7. navigation,
8. navigation,
9. navigation,
10. navigation,
11. Santa Cruz de Tenerife

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

Bridgetown Itinerary Caribbean
from $4,508
price per person Taxes included
Wind Spirit | Nov 18, 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
sold out

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

Bridgetown Itinerary Caribbean
from $4,083
price per person Taxes included
Wind Spirit | Nov 18, 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: Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Martinique

Bridgetown Itinerary Caribbean
from $3,100
price per person Taxes included
4 reservations in 72 hours
Wind Spirit | Dec 28, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Mayreau,
7. Fort de france,
8. Bridgetown
sold out

Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Sri Lanka, Martinique

Bridgetown Itinerary Caribbean
from $3,100
price per person Taxes included
Wind Spirit | Dec 28, 2025
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Pigeon Island,
7. Fort de france,
8. Bridgetown

Caribbean: Barbados, Saint Vincent and the Grenadines, Dominica, Martinique, Saint Kitts and Nevis, Virgin Islands, Antigua and Barbuda, Saint Barthelemy, United Kingdom, Sint Maarten

Bridgetown Itinerary Caribbean
from $3,635
price per person Taxes included
Wind Spirit | Jan 4, 2026
Duration: 10 nights
Departure from: Bridgetown Landing: Philipsburg
Itinerary:
1. Bridgetown,
2. Mayreau,
3. Roseau,
4. Fort de france,
5. Basseterre,
6. St. John ,
7. Falmouth Harbour,
8. Gustavia,
9. Anguilla,
10. Philipsburg
sold out

Barbados, Martinique, Saint Lucia, Sri Lanka, Saint Vincent and the Grenadines, Grenada

Bridgetown Itinerary Caribbean
from $2,893
price per person Taxes included
Wind Surf | Jan 18, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Fort de france,
3. Castries,
4. Pigeon Island,
5. Pigeon Island,
6. Bequia,
7. Mayreau,
8. Saint George,
9. Bridgetown

Caribbean: Barbados, Martinique, Saint Lucia, Sri Lanka, Saint Vincent and the Grenadines, Grenada

Bridgetown Itinerary Caribbean
from $2,893
price per person Taxes included
5 reservations in 72 hours
Wind Surf | Jan 18, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Fort de france,
3. Castries,
4. Pigeon Island,
5. Pigeon Island,
6. Bequia,
7. Mayreau,
8. Saint George,
9. Bridgetown
sold out

Barbados, United Kingdom, Saint Vincent and the Grenadines, Saint Lucia, Netherlands Antilles, Aruba

Bridgetown Itinerary Caribbean
from $3,002
price per person Taxes included
Wind Surf | Jan 25, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Oranjestad
Itinerary:
1. Bridgetown,
2. Man of War Bay,
3. Mayreau,
4. Soufriere,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad

Caribbean: Barbados, United Kingdom, Saint Vincent and the Grenadines, Saint Lucia, Netherlands Antilles, Aruba

Bridgetown Itinerary Caribbean
from $3,002
price per person Taxes included
4 reservations in 72 hours
Wind Surf | Jan 25, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Oranjestad
Itinerary:
1. Bridgetown,
2. Man of War Bay,
3. Mayreau,
4. Soufriere,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad
sold out

Barbados, Saint Kitts and Nevis, Virgin Islands, Guadeloupe, Dominica, Saint Vincent and the Grenadines

Bridgetown Itinerary Caribbean
from $2,887
price per person Taxes included
Wind Spirit | Mar 7, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. St. John ,
5. Les Saintes,
6. Roseau,
7. Mayreau,
8. Bridgetown
sold out

Barbados, Saint Kitts and Nevis, Virgin Islands, Guadeloupe, Dominica, Sri Lanka

Bridgetown Itinerary Caribbean
from $2,887
price per person Taxes included
Wind Spirit | Mar 7, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. St. John ,
5. Les Saintes,
6. Roseau,
7. Pigeon Island,
8. Bridgetown
sold out

Barbados, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, Grenada

Bridgetown Itinerary Caribbean
from $2,781
price per person Taxes included
Wind Spirit | Mar 14, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Pigeon Island,
3. Pigeon Island,
4. Castries,
5. Pitons,
6. Kingstown,
7. Mayreau,
8. Saint George,
9. Bequia,
10. Bridgetown
sold out

Barbados, Sri Lanka, Saint Lucia, Saint Vincent and the Grenadines, Grenada

Bridgetown Itinerary Caribbean
from $2,781
price per person Taxes included
Wind Spirit | Mar 14, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Pigeon Island,
3. Pigeon Island,
4. Castries,
5. Pitons,
6. Kingstown,
7. Mayreau,
8. Saint George,
9. Bequia,
10. Bridgetown
sold out

Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Martinique, Sri Lanka

Bridgetown Itinerary Caribbean
from $2,781
price per person Taxes included
Wind Spirit | Mar 21, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Fort de france,
7. Pigeon Island,
8. Bridgetown

Caribbean: Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Martinique, Saint Vincent and the Grenadines

Bridgetown Itinerary Caribbean
from $2,781
price per person Taxes included
2 reservations in 72 hours
Wind Spirit | Mar 21, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Fort de france,
7. Mayreau,
8. Bridgetown

Ocean Cruises: Barbados, Portugal, Netherlands

Bridgetown Itinerary Ocean Cruises
from $2,672
price per person Taxes included
Star Pride | Mar 22, 2026
Duration: 16 nights
Departure from: Bridgetown Landing: Amsterdam
Itinerary:
1. Bridgetown,
2. navigation,
3. navigation,
4. navigation,
5. navigation,
6. navigation,
7. navigation,
8. navigation,
9. navigation,
10. navigation,
11. navigation,
12. Lisbon,
13. navigation,
14. navigation,
15. navigation,
16. navigation,
17. Amsterdam

Ocean Cruises: Barbados, Portugal

Bridgetown Itinerary Ocean Cruises
from $2,684
price per person Taxes included
Wind Spirit | Mar 28, 2026
Duration: 15 nights
Departure from: Bridgetown Landing: Lisbon
Itinerary:
1. Bridgetown,
2. navigation,
3. navigation,
4. navigation,
5. navigation,
6. navigation,
7. navigation,
8. navigation,
9. navigation,
10. navigation,
11. navigation,
12. navigation,
13. navigation,
14. navigation,
15. navigation,
16. Lisbon
sold out

Barbados, Portugal

Bridgetown Itinerary Ocean Cruises
from $2,684
price per person Taxes included
Wind Spirit | Mar 28, 2026
Duration: 15 nights
Departure from: Bridgetown Landing: Lisbon
Itinerary:
1. Bridgetown,
2. navigation,
3. navigation,
4. navigation,
5. navigation,
6. navigation,
7. navigation,
8. navigation,
9. navigation,
10. navigation,
11. navigation,
12. navigation,
13. navigation,
14. navigation,
15. navigation,
16. Lisbon
31 cruises