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14-Night Caribbean
Cruise
Departs
San Juan, Puerto Rico
Sailing
Nov 29 - Dec 13, 2026
Windstar Cruises - Star Pride
Prices from
$5,750
14-Night Caribbean Cruise
Windstar Cruises -
Star Pride
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1-888-447-8459
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Oceanview
From
$5,750
Balcony
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Suite
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Deals on this Cruise
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Other dates for this cruise
Sail Date
Brochure
Our Price
Savings
Deals
Cruise Itinerary
Departs
San Juan, Puerto Rico
Sailing
Nov 29 - Dec 13, 2026
Day 1
Nov 29
San Juan
Puerto Rico, United States
Departs
7:00PM
Day 2
Nov 30
Cruz Bay
St. John, United States Virgin Islands
Arrives
8:00AM
|
Departs
6:00PM
Day 3
Dec 1
Gustavia
Saint Barthélemy, France
Arrives
8:00AM
|
Departs
10:00PM
Day 4
Dec 2
Basseterre
St. Kitts, St. Kitts And Nevis
Arrives
8:00AM
|
Departs
5:00PM
Day 5
Dec 3
Philipsburg
Sint Maarten
Arrives
8:00AM
|
Departs
10:00PM
Day 6
Dec 4
Great Harbour
Jost Van Dyke, British Virgin Islands
Arrives
9:00AM
|
Departs
10:00PM
Day 7
Dec 5
Prickly Pear
British Virgin Islands
Arrives
8:00AM
|
Departs
5:00PM
Day 8
Dec 6
San Juan
Puerto Rico, United States
Arrives
7:00AM
|
Departs
7:00PM
Day 9
Dec 7
At Sea
Day 10
Dec 8
Saint George's
Grenada
Arrives
9:00AM
|
Departs
10:00PM
Day 11
Dec 9
Bequia
Saint Vincent And The Grenadines
Arrives
8:00AM
|
Departs
10:00PM
Day 12
Dec 10
Mayreau
Saint Vincent And The Grenadines
Arrives
8:00AM
|
Departs
4:30PM
Day 13
Dec 11
Deshaies
Guadeloupe, France
Arrives
11:00AM
|
Departs
6:00PM
Day 14
Dec 12
Marigot
St. Martin, France
Arrives
8:00AM
|
Departs
3:00PM
Day 15
Dec 13
San Juan
Puerto Rico, United States
Arrives
7:00AM
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, friendly crew, and intimate small-ship atmosphere. Guests consistently highlight the quality of food, comfortable cabins, and unique itineraries. While most experiences are overwhelmingly positive, some guests note areas for improvement, such as occasional issues with excursions, ship maintenance, and specialty dining. Overall, the cruise delivers a premium, personalized experience with a few minor drawbacks.
AI-generated from the text of customer reviews
select to learn more
“Stunning Iceland”
Cruise Date:
07/21/2025
Destination:
Europe
Reviewed 11 months ago by
Steffenie
Cruise Date:
07/21/2025
Destination:
Europe
Reviewed 11 months ago by
Peter
Cruise Date:
03/01/2025
Destination:
Panama Canal
Reviewed over 1 year ago by
David
“Honeymoon ”
Cruise Date:
02/08/2025
Destination:
Caribbean
Reviewed over 1 year ago by
Jeramiah
“Perfect 1st Cruise”
Cruise Date:
11/09/2024
Destination:
Caribbean
Reviewed over 1 year ago by
Paul