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14-Night Caribbean
Cruise
Departs
San Juan, Puerto Rico
Sailing
Nov 15 - 29, 2026
Windstar Cruises - Star Pride
Prices from
$3,999
14-Night Caribbean Cruise
Windstar Cruises -
Star Pride
Speak To A Vacation Planner
1-888-447-8459
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Oceanview
From
$3,999
Balcony
From
$6,419
Suite
From
$8,899
Deals on this Cruise
- Avoya's Exclusive Deals with Windstar Cruises!
- Yacht Club Past Guest Rewards – Save up to 10%, up to $100 Free Onboard Credit, Private Cocktail Reception PLUS More!
Call
1-888-447-8459
1-888-447-8459
to be connected with a
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Cruise Itinerary
Departs
San Juan, Puerto Rico
Sailing
Nov 15 - 29, 2026
Day 1
Nov 15
San Juan
Puerto Rico, United States
Departs
7:00PM
Day 2
Nov 16
Cruz Bay
St. John, United States Virgin Islands
Arrives
8:00AM
|
Departs
6:00PM
Day 3
Nov 17
Basseterre
St. Kitts, St. Kitts And Nevis
Arrives
8:00AM
|
Departs
5:00PM
Day 4
Nov 18
Gustavia
Saint Barthélemy, France
Arrives
7:00AM
|
Departs
10:00PM
Day 5
Nov 19
Philipsburg
Sint Maarten
Arrives
8:00AM
|
Departs
10:00PM
Day 6
Nov 20
Great Harbour
Jost Van Dyke, British Virgin Islands
Arrives
9:00AM
|
Departs
10:00PM
Day 7
Nov 21
Prickly Pear
British Virgin Islands
Arrives
8:00AM
|
Departs
5:00PM
Ship Reviews
* All reviews are by verified customers that have
traveled by booking through a travel agent in the
Avoya Network
customers say
Windstar's Star Pride receives high praise for its exceptional service, outstanding crew, and intimate small-ship atmosphere. Guests consistently highlight the quality of food, comfortable accommodations, and well-organized excursions. While most reviews are overwhelmingly positive, some guests note areas for improvement, such as ship maintenance, occasional underwhelming meals, and disappointing or overpriced excursions. The ship's smaller size and attentive staff create a personalized and welcoming experience, making it a favorite for many repeat cruisers.
AI-generated from the text of customer reviews
select to learn more
Cruise Date:
03/01/2025
Destination:
Panama Canal
Reviewed 4 months ago by
David
“Honeymoon ”
Cruise Date:
02/08/2025
Destination:
Caribbean
Reviewed 5 months ago by
Jeramiah
“Perfect 1st Cruise”
Cruise Date:
11/09/2024
Destination:
Caribbean
Reviewed 8 months ago by
Paul
“1st, but not the last Windstar Cruise”
Cruise Date:
08/09/2024
Destination:
Europe
Reviewed 11 months ago by
Martha
“Great cruise, great travel agent!”
Cruise Date:
12/30/2023
Destination:
Central America
Reviewed over 1 year ago by
Frances