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

Pricing

Per person, starting from

Book This Cruise

An advisor confirms everything with you.

Trip Details

Departs: November 29, 2026

Returns: December 13, 2026

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.

Compare dates ↓

6 cruises leaving the same week

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

See alternatives ↓

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.

Call 213-998-7123Ask About This Cruise

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 8, 2026
November 15, 2026
November 22, 2026
November 29, 2026This sailing
December 6, 2026
December 13, 2026
December 20, 2026
December 27, 2026
January 3, 2027
November 1, 2027
November 8, 2027
November 15, 2027
December 20, 2027

Compare Alternatives

Sailing the Same Week

Other vacations of about the same length leaving within a few days of November 29, 2026, nearest departure ports first.

Princess Cruises • 14 Nights

Eastern/Western Caribbean Adventurer with Celebration Key

Sun Princess

Nov 29, 2026 • departs Ft. Lauderdale

From

Norwegian Cruise Line • 12 Nights

12-Day Caribbean Round-trip New York: Dominican Republic & St. Thomas

Norwegian Bliss

Nov 29, 2026 • departs New York

From

Holland America Line • 12 Nights

12-DAY EASTERN CARIBBEAN: BARBADOS, ST. LUCIA & ST. KITTS

Nieuw Amsterdam

Nov 29, 2026 • departs Fort Lauderdale

From

MSC Cruises • 14 Nights

14-Night Caribbean & Bahamas from Miami

MSC Meraviglia

Nov 29, 2026 • departs Miami

From

Norwegian Cruise Line • 12 Nights

12-Night Caribbean

Norwegian Gem

Nov 28, 2026 • departs Tampa

From

Holland America Line • 14 Nights

14-DAY EASTERN & WESTERN CARIBBEAN: SAN JUAN & MEXICO

Eurodam

Nov 28, 2026 • departs Fort Lauderdale

From