On December 24, we will be open from 9:00 a.m. to 1:00 p.m. We will see you again on Saturday the 27th. Merry Christmas!
home › Windstar Cruises › All Caribbean Cruises with Windstar Cruises

All Caribbean Cruises with Windstar Cruises

  • 2026
  • 2027
December 2025
January 2026 February 2026 March 2026 April 2026 May 2026 June 2026 July 2026 August 2026 September 2026 October 2026 November 2026 December 2026
January 2027 February 2027 March 2027
90 cruises
Caribbean: Aruba, Netherlands Antilles, Saint Vincent and the Grenadines, Saint Lucia, Trinidad and Tobago, Barbados
Oranjestad Itinerary Caribbean
Suite from ₹2,83,522
price per person Taxes included
See the cruise Book Online Book Online
Star Pride | 15-Mar-2026
Duration: 7 nights
Departure from: Oranjestad Landing: Bridgetown
Itinerary:
1. Oranjestad,
2. Kralendijk,
3. navigation,
4. Kingstown,
5. Pitons,
6. Bequia,
7. Mayreau,
8. Scarborough,
9. Bridgetown
Caribbean: United States, Bermuda, Grenada, Antigua and Barbuda
Boston Itinerary Caribbean
Suite from ₹3,02,879
price per person Taxes included
See the cruise Book Online Book Online
Star Pride | 20-Oct-2026
Duration: 8 nights
Departure from: Boston Landing: Saint Johns
Itinerary:
1. Boston,
2. navigation,
3. navigation,
4. Hamilton,
5. Hamilton,
6. Saint George,
7. Saint George,
8. navigation,
9. navigation,
10. Saint Johns
Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from ₹3,07,123
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 02-Jan-2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
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
sold out
Barbados, Saint Kitts and Nevis, Guadeloupe, Dominica, Saint Vincent and the Grenadines, Martinique
Bridgetown Itinerary Caribbean
External from ₹3,09,607
price per person Taxes included
Wind Spirit | 28-Dec-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
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Kitts and Nevis, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from ₹3,15,818
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 06-Mar-2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
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
Philipsburg Itinerary Caribbean
External from ₹3,15,818
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 06-Feb-2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
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
Philipsburg Itinerary Caribbean
External from ₹3,15,818
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 20-Mar-2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
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
Philipsburg Itinerary Caribbean
External from ₹3,15,818
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 23-Jan-2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Basseterre,
7. Gustavia,
8. Philipsburg
Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from ₹3,17,474
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 13-Mar-2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
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: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from ₹3,17,474
price per person Taxes included
See the cruise Book Online Book Online
Wind Surf | 30-Jan-2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Tortola Island,
4. Jost Van Dyke,
5. Jost Van Dyke,
6. Virgin Gorda,
7. Gustavia,
8. navigation,
9. Philipsburg
90 cruises