San Juan
Photo: Diego F. Parra · Re-encoded to WebP.
Windstar Cruises
Star Collector: Lovely Leewards
Caribbean
Photo: Mike1979 Russia · CC BY-SA 3.0 (share-alike) · Re-encoded to WebP.
Sailing Itinerary
Trip Details
Speak With A Specialist
Ready to Book?
Our travel experts are standing by to help plan the perfect getaway. Call us, or send a note and we will come back to you.
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
Basseterre
Philipsburg
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 1, 2027 | |||||
| November 8, 2027 | |||||
| November 15, 2027 | |||||
| December 20, 2027This sailing | |||||
| December 27, 2027 | |||||
| January 3, 2028 | |||||
| January 10, 2028 | |||||
| January 17, 2028 | |||||
| January 24, 2028 | |||||
| January 31, 2028 | |||||
| February 7, 2028 | |||||
| February 14, 2028 | |||||
| March 13, 2028 |
Compare Alternatives
Sailing the Same Week
Other vacations of about the same length leaving within a few days of December 20, 2027, nearest departure ports first.
Princess Cruises • 14 Nights
Southern Caribbean Adventurer Holiday
Emerald Princess
Dec 19, 2027 • departs San Juan
From
Princess Cruises • 14 Nights
Circle Caribbean Holiday
Island Princess
Dec 20, 2027 • departs Ft. Lauderdale
From
Regent Seven Seas Cruises • 16 Nights
HOLIDAY IN PANAMA
Seven Seas Splendor
Dec 20, 2027 • departs Miami
From
MSC Cruises • 14 Nights
14-Night Southern Caribbean from La Romana
MSC Opera
Dec 20, 2027 • departs La Romana
From
Princess Cruises • 14 Nights
Eastern/Western Caribbean Adventurer Holiday
Sky Princess
Dec 19, 2027 • departs Ft. Lauderdale
From
Costa Cruises • 14 Nights
Caribbean & Antilles from La Romana
Costa Fascinosa
Dec 19, 2027 • departs La Romana
From