$ Argentina
A$ Australia
$CAN Canada
¥ China
€ France
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₹ India
€ Italy
¥ Japan
Mex$ Mexico
$ New Zealand
₽ Russian Federation
R South Africa
€ Spain
CHF Switzerland
£ United Kingdom
$ United States
$ Uruguay
All Caribbean Cruises with Windstar Cruises
- 2025
- 2026
- 2027
January 2026
February 2026
March 2026
April 2026
May 2026
June 2026
July 2026
August 2026
September 2026
October 2026
November 2026
December 2026
76 cruises
Caribbean: United States, Antigua and Barbuda
from $3,935
price per person Taxes included
price per person Taxes included
Book Online
Itinerary:
1. New York,
2. navigation,
3. navigation,
4. Saint Johns,
5. Saint Johns,
6. navigation,
7. navigation,
8. Saint Johns
Caribbean: Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands
from $3,683
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands
from $4,317
price per person Taxes included
price per person Taxes included
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
from $4,642
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands
from $4,642
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Puerto Rico, Grenada, Saint Vincent and the Grenadines, Sri Lanka, Guadeloupe, Saint Martin
from $4,265
price per person Taxes included
price per person Taxes included
Itinerary:
1. San Juan,
2. navigation,
3. Saint George,
4. Bequia,
5. Pigeon Island,
6. Les Saintes,
7. Marigot,
8. San Juan
Caribbean: Antigua and Barbuda, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin
from $4,265
price per person Taxes included
price per person Taxes included
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
from $4,317
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands
from $4,317
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Basseterre,
4. Gustavia,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Barbados, Saint Vincent and the Grenadines, Antigua and Barbuda, Netherlands Antilles, Aruba, Spain, Panama
from $6,229
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. Bequia,
3. Mayreau,
4. Saint Johns,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad,
9. navigation,
10. Cartagena ,
11. navigation,
12. Colon
Caribbean: Barbados, Saint Vincent and the Grenadines, Antigua and Barbuda, Netherlands Antilles, Aruba, Spain, Panama
from $6,878
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. Bequia,
3. Mayreau,
4. Saint Johns,
5. navigation,
6. Kralendijk,
7. Willemstad,
8. Oranjestad,
9. navigation,
10. Cartagena ,
11. navigation,
12. Colon
Puerto Rico, Grenada, Saint Vincent and the Grenadines, Sri Lanka, Guadeloupe, Saint Martin
from $4,265
price per person Taxes included
price per person Taxes included
Itinerary:
1. San Juan,
2. navigation,
3. Saint George,
4. Bequia,
5. Pigeon Island,
6. Les Saintes,
7. Marigot,
8. San Juan
Caribbean: Antigua and Barbuda, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin
from $4,265
price per person Taxes included
price per person Taxes included
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
from $4,317
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Gustavia,
4. Basseterre,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Antigua and Barbuda, Virgin Islands, Saint Barthelemy, Saint Kitts and Nevis, Sint Maarten, British Virgin Islands
from $4,317
price per person Taxes included
price per person Taxes included
Itinerary:
1. Saint Johns,
2. St. John ,
3. Gustavia,
4. Basseterre,
5. Philipsburg,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Saint Johns
Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
from $3,325
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Jost Van Dyke,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Gustavia,
7. Philipsburg
Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
from $3,487
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Jost Van Dyke,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Gustavia,
7. Philipsburg
Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
from $3,813
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
from $3,813
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
from $4,001
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. navigation,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
Caribbean: Aruba, Netherlands Antilles, Antigua and Barbuda, Saint Vincent and the Grenadines, Barbados
from $4,746
price per person Taxes included
price per person Taxes included
Itinerary:
1. Oranjestad,
2. Willemstad,
3. Kralendijk,
4. navigation,
5. Saint Johns,
6. Saint Johns,
7. Mayreau,
8. Bequia,
9. Bridgetown
Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
from $4,462
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
from $4,786
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Sri Lanka, Martinique
from $4,729
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Pigeon Island,
7. Fort de france,
8. Bridgetown
Caribbean: Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Martinique
from $5,054
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. navigation,
3. Basseterre,
4. Les Saintes,
5. Roseau,
6. Mayreau,
7. Fort de france,
8. Bridgetown
Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
from $4,488
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. navigation,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
from $4,233
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. navigation,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
Caribbean: Barbados, Saint Vincent and the Grenadines, Dominica, Martinique, France, Saint Kitts and Nevis, Antigua and Barbuda, Saint Barthelemy, British Virgin Islands, Sint Maarten
from $5,547
price per person Taxes included
price per person Taxes included
Itinerary:
1. Bridgetown,
2. Mayreau,
3. Roseau,
4. Fort de france,
5. Deshaies,
6. Basseterre,
7. Saint Johns,
8. navigation,
9. Gustavia,
10. Tortola Island,
11. Philipsburg
Caribbean: Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Antigua and Barbuda, Guadeloupe, Saint Vincent and the Grenadines, Barbados
from $4,437
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. Saint Johns,
5. Les Saintes,
6. Mayreau,
7. Kingstown,
8. Bridgetown
Sint Maarten, Saint Kitts and Nevis, Saint Barthelemy, Virgin Islands, Guadeloupe, Sri Lanka, Saint Vincent and the Grenadines, Barbados
from $4,275
price per person Taxes included
price per person Taxes included
Itinerary:
1. Philipsburg,
2. Basseterre,
3. Gustavia,
4. St. John ,
5. Les Saintes,
6. Pigeon Island,
7. Kingstown,
8. Bridgetown
76 cruises
