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All Caribbean Cruises with Windstar Cruises

  • 2027
  • 2028
October 2026 November 2026 December 2026
January 2027 February 2027 March 2027 April 2027 May 2027 June 2027 July 2027 August 2027 September 2027 October 2027 November 2027 December 2027
January 2028 February 2028 March 2028
119 cruises
Caribbean: Sint Maarten, British Virgin Islands, Saint Barthelemy, Virgin Islands
Philipsburg Itinerary Caribbean
External from $4,559
price per person Taxes included
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Wind Surf | Jan. 3, 2028
Duration: 6 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Tortola Island,
3. Gustavia,
4. Jost Van Dyke,
5. Virgin Gorda,
6. Tortola Island,
7. Philipsburg
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Barthelemy, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
External from $4,697
price per person Taxes included
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Wind Surf | Nov. 28, 2027
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Charlestown,
3. Roseau,
4. Mayreau,
5. Les Saintes,
6. Gustavia,
7. Basseterre,
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 $4,697
price per person Taxes included
See the cruise Book
Wind Surf | Dec. 12, 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: Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from $4,715
price per person Taxes included
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Star Pride | Nov. 1, 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
Caribbean: Antigua and Barbuda, Virgin Islands, Saint Kitts and Nevis, Saint Barthelemy, Sint Maarten, British Virgin Islands
Saint Johns Itinerary Caribbean
Suite from $4,715
price per person Taxes included
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Star Pride | Nov. 15, 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
Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $4,723
price per person Taxes included
See the cruise Book
Wind Surf | Dec. 5, 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: United States, Bermuda, Grenada, Antigua and Barbuda
Boston Itinerary Caribbean
Suite from $4,821
price per person Taxes included
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Star Pride | Oct. 20, 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: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin
Saint Johns Itinerary Caribbean
Suite from $4,827
price per person Taxes included
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Star Pride | Nov. 22, 2027
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns
Caribbean: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin
Saint Johns Itinerary Caribbean
Suite from $4,827
price per person Taxes included
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Star Pride | Nov. 8, 2027
Duration: 7 nights
Departure from: Saint Johns Landing: Saint Johns
Itinerary:
1. Saint Johns,
2. navigation,
3. Saint George,
4. Bequia,
5. Mayreau,
6. Les Saintes,
7. Marigot,
8. Saint Johns
Caribbean: Sint Maarten, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $4,888
price per person Taxes included
See the cruise Book
Wind Surf | Jan. 30, 2028
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
119 cruises