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11-Night Caribbean Cruise
Departs San Juan, Puerto Rico
Sailing Oct 28 - Nov 8, 2026
Windstar Cruises - Star Pride
Prices from
$3,599

11-Night Caribbean Cruise

Windstar Cruises - Star Pride
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Oceanview

From
$3,599

Balcony

From
$6,019

Suite

From
$8,499

Deals on this Cruise

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Cruise Itinerary

Departs San Juan, Puerto Rico
Sailing Oct 28 - Nov 8, 2026
Day 1
Oct 28
San Juan
Puerto Rico, United States
Departs 7:00PM
Day 2
Oct 29
Cruz Bay
St. John, United States Virgin Islands
Arrives 8:00AM  |  Departs 6:00PM
Day 3
Oct 30
Gustavia
Saint Barthélemy, France
Arrives 8:00AM  |  Departs 10:00PM
Day 4
Oct 31
Basseterre
St. Kitts, St. Kitts And Nevis
Arrives 8:00AM  |  Departs 6:00PM
Day 5
Nov 1
Falmouth Bay
Antigua, Antigua And Barbuda
Arrives 8:00AM  |  Departs 6:00PM
Day 6
Nov 2
îLes Des Saintes
Guadeloupe, France
Arrives 8:00AM  |  Departs 6:00PM
Day 7
Nov 3
Pigeon Island
St. Lucia
Arrives 8:00AM  |  Departs 9:30PM
Day 8
Nov 4
Saint George's
Grenada
Arrives 10:00AM  |  Departs 6:00PM
Day 9
Nov 5
At Sea
Day 10
Nov 6
Great Harbour
Jost Van Dyke, British Virgin Islands
Arrives 8:00AM  |  Departs 10:00PM
Day 11
Nov 7
Prickly Pear
British Virgin Islands
Arrives 8:00AM  |  Departs 5:00PM
Day 12
Nov 8
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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