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14-Night Caribbean Cruise
Departs San Juan, Puerto Rico
Sailing Nov 8 - 22, 2026
Windstar Cruises - Star Pride
Prices from
$3,999

14-Night Caribbean Cruise

Windstar Cruises - Star Pride
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Oceanview

From
$3,999

Balcony

From
$6,419

Suite

From
$8,899

Deals on this Cruise

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Other dates for this cruise

Brochure
-
Our Price
$5,099
Savings
-
Deals
2 Deals

Cruise Itinerary

Departs San Juan, Puerto Rico
Sailing Nov 8 - 22, 2026
Day 1
Nov 8
San Juan
Puerto Rico, United States
Departs 7:00PM
Day 2
Nov 9
At Sea
Day 3
Nov 10
Saint George's
Grenada
Arrives 9:00AM  |  Departs 10:00PM
Day 4
Nov 11
Bequia
Saint Vincent And The Grenadines
Arrives 8:00AM  |  Departs 10:00PM
Day 5
Nov 12
Mayreau
Saint Vincent And The Grenadines
Arrives 8:00AM  |  Departs 5:00PM
Day 6
Nov 13
îLes Des Saintes
Guadeloupe, France
Arrives 10:00AM  |  Departs 5:00PM
Day 7
Nov 14
Marigot
St. Martin, France
Arrives 8:00AM  |  Departs 3:00PM
Day 8
Nov 15
San Juan
Puerto Rico, United States
Arrives 7:00AM  |  Departs 7:00PM
Day 9
Nov 16
Cruz Bay
St. John, United States Virgin Islands
Arrives 8:00AM  |  Departs 6:00PM
Day 10
Nov 17
Basseterre
St. Kitts, St. Kitts And Nevis
Arrives 8:00AM  |  Departs 5:00PM
Day 11
Nov 18
Gustavia
Saint Barthélemy, France
Arrives 7:00AM  |  Departs 10:00PM
Day 12
Nov 19
Philipsburg
Sint Maarten
Arrives 8:00AM  |  Departs 10:00PM
Day 13
Nov 20
Great Harbour
Jost Van Dyke, British Virgin Islands
Arrives 9:00AM  |  Departs 10:00PM
Day 14
Nov 21
Prickly Pear
British Virgin Islands
Arrives 8:00AM  |  Departs 5:00PM
Day 15
Nov 22
San Juan
Puerto Rico, United States
Arrives 7:00AM
4.5 (95)
* 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 and attentive crew, and overall intimate small-ship experience. Guests consistently highlight the quality of food, spacious and comfortable cabins, and the unique itineraries that visit less-traveled ports. While most reviews are very positive, some guests note areas for improvement, such as occasional issues with ship maintenance, inconsistent food quality in certain venues, and disappointing or overpriced excursions. The ship's atmosphere is described as relaxed and personal, with a strong sense of camaraderie among guests and crew. Overall, Star Pride is highly recommended for travelers seeking a boutique cruise experience, though some aspects like excursions and ship age may not meet everyone's expectations.

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