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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
127 cruises
Caribbean: Sint Maarten, United States, Dominica, Saint Vincent and the Grenadines, Guadeloupe, Saint Barthelemy, Saint Kitts and Nevis
Philipsburg Itinerary Caribbean
External from $3,537
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, British Virgin Islands, Saint Barthelemy, Virgin Islands
Philipsburg Itinerary Caribbean
External from $3,564
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, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $3,736
price per person Taxes included
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Wind Surf | Mar. 12, 2028
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Saint Johns,
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 $3,736
price per person Taxes included
See the cruise Book
Wind Surf | Feb. 27, 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
Caribbean: Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $3,736
price per person Taxes included
See the cruise Book
Wind Surf | Feb. 13, 2028
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Saint Johns,
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 $3,736
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
Caribbean: Sint Maarten, Antigua and Barbuda, British Virgin Islands, Virgin Islands, Saint Barthelemy
Philipsburg Itinerary Caribbean
External from $3,736
price per person Taxes included
See the cruise Book
Wind Surf | Jan. 16, 2028
Duration: 7 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Saint Johns,
3. Tortola Island,
4. Tortola Island,
5. Jost Van Dyke,
6. Jost Van Dyke,
7. Virgin Gorda,
8. Gustavia,
9. Philipsburg
Caribbean: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin
Saint Johns Itinerary Caribbean
Suite from $3,777
price per person Taxes included
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Star Pride | Nov. 22, 2026
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, Saint Barthelemy, Antigua and Barbuda, France, British Virgin Islands, Virgin Islands
Philipsburg Itinerary Caribbean
External from $3,794
price per person Taxes included
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Wind Surf | Nov. 20, 2027
Duration: 8 nights
Departure from: Philipsburg Landing: Philipsburg
Itinerary:
1. Philipsburg,
2. Gustavia,
3. Saint Johns,
4. Deshaies,
5. Tortola Island,
6. Tortola Island,
7. Jost Van Dyke,
8. Jost Van Dyke,
9. Virgin Gorda,
10. Philipsburg
Caribbean: Antigua and Barbuda, Grenada, Saint Vincent and the Grenadines, Guadeloupe, Saint Martin
Saint Johns Itinerary Caribbean
Suite from $3,848
price per person Taxes included
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Star Legend | Feb. 21, 2028
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
127 cruises