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All Caribbean Cruises with Windstar Cruises

  • 2026
  • 2027
93 cruises
Boston Itinerary Caribbean
Suite from $3,997
price per person Taxes included
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
Philipsburg Itinerary Caribbean
External from $4,229
price per person Taxes included
Wind Surf | Jan. 2, 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
Philipsburg Itinerary Caribbean
External from $4,367
price per person Taxes included
Wind Surf | Mar. 20, 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
Philipsburg Itinerary Caribbean
External from $4,367
price per person Taxes included
Wind Surf | Jan. 23, 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
Philipsburg Itinerary Caribbean
External from $4,367
price per person Taxes included
Wind Surf | Mar. 6, 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
Philipsburg Itinerary Caribbean
External from $4,367
price per person Taxes included
Wind Surf | Feb. 6, 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
Philipsburg Itinerary Caribbean
External from $4,394
price per person Taxes included
Wind Surf | Mar. 13, 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
Philipsburg Itinerary Caribbean
External from $4,394
price per person Taxes included
Wind Surf | Jan. 30, 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
Saint Johns Itinerary Caribbean
Suite from $4,498
price per person Taxes included
Star Pride | Dec. 6, 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
Bridgetown Itinerary Caribbean
Suite from $4,511
price per person Taxes included
Star Legend | Nov. 27, 2026
Duration: 7 nights
Departure from: Bridgetown Landing: Bridgetown
Itinerary:
1. Bridgetown,
2. Fort de france,
3. Pigeon Island,
4. Pigeon Island,
5. Castries,
6. Pitons,
7. Mayreau,
8. Saint George,
9. Bequia,
10. Bridgetown
93 cruises