A white luxury cruise ship named "Seabourn Pride" cruising on choppy dark blue water. The multi-deck vessel features white radar domes, orange lifeboats near the stern, and small figures of passengers visible on the upper open-air decks under a cloudy blue sky.

Windstar Cruises

Star Collector: Lovely Leewards

Caribbean

Photo: Mike1979 Russia · CC BY-SA 3.0 (share-alike) · Re-encoded to WebP.

Sailing Itinerary

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Trip Details

Departs: November 1, 2027

Returns: November 15, 2027

Departure Port: San Juan

Ship: Star Pride

Before You Decide

12 other departures of this route

The identical itinerary, priced week by week. The gap is often hundreds of dollars.

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6 cruises leaving the same week

Other ships and other routes of about this length, from ports near this one.

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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
More About Star Pride

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
Read the Full Guide
Aerial shot of a tropical beach with a pier, turquoise waters, and a resort in Cozumel.

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.

DepartsFrom
November 1, 2027This sailing
November 8, 2027
November 15, 2027
December 20, 2027
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

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