Eastern Caribbean Oct 2026 11 nights Windstar Cruises San Juan

San Juan → Cruz Bay, Saint John → Saint-Barthélemy → San Juan

via Basseterre, Saint Kitts, Spanish Town (Virgin Gorda), and 5 more

Star Pride

11 nights

October 28–November 8, 2026

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Star Pride • October 28, 2026 • departs in about 1 month

Last 90 days

What should you book?

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What kind of trip is this?

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Port-heavy itinerary with stops in Puerto Rico, Virgin Islands, U.S., and Saint Barthélemy, and 6 other countries

  • 11 nights
  • 9 ports
  • 1 sea day
  • Star Ship Megayacht-class ship
  • Round-trip sailing
  • San Juan ↔

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Embark port
Disembark port
Port of call

Route

San Juan → Cruz Bay, Saint John → Saint-Barthélemy → Basseterre, Saint Kitts → Falmouth + 6 more

Expand full itinerary
  1. 1

    San Juan, Puerto Rico

    Wednesday, Oct 28, 2026

    Dep 7:00 PM
  2. 2
    Arr 8:00 AM
    Dep 6:00 PM
  3. 3
    Arr 8:00 AM
    Dep 10:00 PM
  4. 4
    Arr 8:00 AM
    Dep 6:00 PM
  5. 5

    Falmouth, Antigua and Barbuda

    Sunday, Nov 1, 2026

    Arr 8:00 AM
    Dep 6:00 PM
  6. 6
    Arr 8:00 AM
    Dep 6:00 PM
  7. 7

    Rodney Bay, Saint Lucia

    Tuesday, Nov 3, 2026

    Arr 8:00 AM
    Dep 9:30 PM
  8. 8

    Saint George's, Grenada

    Wednesday, Nov 4, 2026

    Arr 10:00 AM
    Dep 6:00 PM
  9. 9
    Arr 8:00 AM
    Dep 10:00 PM
  10. 10
    Arr 8:00 AM
    Dep 5:00 PM
  11. 11

    San Juan, Puerto Rico

    Sunday, Nov 8, 2026

    Arr 7:00 AM
    Dep 12:00 PM

Embarks in San Juan, Puerto Rico • ends in San Juan, Puerto Rico • 9 ports of call • 1 sea days

The ship

Star Pride is a Star Ship megayacht ship carrying about 343 guests.

Windstar Cruises logo

Star Pride

Cruise line
Windstar Cruises
Class
Star Ship megayacht
Capacity
343 guests
Built
1988

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