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8-Night Caribbean
Cruise
Departs
Boston, Massachusetts
Sailing
Oct 20 - 28, 2026
Windstar Cruises - Star Pride
Prices from
$2,426
8-Night Caribbean Cruise
Windstar Cruises -
Star Pride
Speak To A Vacation Planner
1-888-447-8459
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Oceanview
From
$2,426
Balcony
From
$3,686
Suite
From
$4,926
Deals on this Cruise
- Cyber Week!
- Yacht Club Past Guest Rewards – Save up to 10%, up to $100 Free Onboard Credit, Private Cocktail Reception PLUS More!
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1-888-447-8459
1-888-447-8459
to be connected with a
travel professional today!
Cruise Itinerary
Departs
Boston, Massachusetts
Sailing
Oct 20 - 28, 2026
Day 1
Oct 20
Boston
Massachusetts, United States
Departs
5:00PM
Day 2
Oct 21
At Sea
Day 3
Oct 22
At Sea
Day 4
Oct 23
Hamilton
Bermuda
Arrives
8:45AM
Day 5
Oct 24
Hamilton
Bermuda
Departs
7:00AM
Saint George's
Bermuda
Arrives
10:00AM
Day 6
Oct 25
Saint George's
Bermuda
Departs
7:00AM
Day 7
Oct 26
At Sea
Day 8
Oct 27
At Sea
Day 9
Oct 28
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 and attentive crew, and intimate small-ship atmosphere. Guests consistently highlight the quality of food, comfortable cabins, and unique itineraries. While most reviews are positive, some guests note areas for improvement, such as occasional issues with ship maintenance, inconsistent food quality, and disappointing or overpriced excursions. Overall, the cruise experience is described as relaxing, personal, and memorable, making it a favorite among those seeking a more boutique cruise experience.
AI-generated from the text of customer reviews
select to learn more
“Stunning Iceland”
Cruise Date:
07/21/2025
Destination:
Europe
Reviewed 4 months ago by
Steffenie
Cruise Date:
07/21/2025
Destination:
Europe
Reviewed 4 months ago by
Peter
Cruise Date:
03/01/2025
Destination:
Panama Canal
Reviewed 9 months ago by
David
“Honeymoon ”
Cruise Date:
02/08/2025
Destination:
Caribbean
Reviewed 9 months ago by
Jeramiah
“Perfect 1st Cruise”
Cruise Date:
11/09/2024
Destination:
Caribbean
Reviewed about 1 year ago by
Paul