San Juan
Photo: Diego F. Parra · Re-encoded to WebP.
Windstar Cruises
Windward Islands Surf & Sunsets
Caribbean
Photo: Mike1979 Russia · CC BY-SA 3.0 (share-alike) · Re-encoded to WebP.
Sailing Itinerary
Trip Details
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Your Ship
Star Pride
The first Seabourn hull Windstar bought, and the last one it cut in half
Aboard
- Completed in November 1988 as Seabourn Pride and christened by Shirley Temple Black
- The first of the three ex-Seabourn yachts Windstar acquired, in 2014
- The last of the three through the Star Plus stretch, delivered from Palermo in October 2021
- Lost six months in 2016 after grounding on a reef off Panama
- Summers circumnavigating Iceland from Reykjavik, winters in the Caribbean from San Juan
Ashore
Where You Stop
San Juan
Caribbean
The Caribbean
The most-sailed water on earth, and the easiest cruise to fall in love with, short flights, warm water twelve months a year, and a different island every morning.
- Best Time to Go
- December through April, outside hurricane season
- Typical Length
- 5 to 8 nights
Compare Dates
The Same Trip, Other Weeks
The identical itinerary on this ship, priced by departure. Fares move week to week, and the difference is often larger than anything else on this page.
| Departs | Inside | Oceanview | Balcony | Suite | From |
|---|---|---|---|---|---|
| November 22, 2026 | |||||
| December 6, 2026 | |||||
| December 20, 2026 | |||||
| January 3, 2027 | |||||
| November 8, 2027 | |||||
| November 22, 2027 | |||||
| December 27, 2027 | |||||
| January 10, 2028This sailing | |||||
| January 24, 2028 | |||||
| February 7, 2028 | |||||
| February 21, 2028 | |||||
| March 13, 2028 | |||||
| March 27, 2028 |
Compare Alternatives
Sailing the Same Week
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Princess Cruises • 7 Nights
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Jan 9, 2028 • departs San Juan
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Jan 10, 2028 • departs Santo Domingo
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