No Avoya Fees on Cruises or Tours. Book, change, or cancel without paying any Avoya fees. Plus, our Low Price Guarantee! No Avoya Fees on Cruises or Tours.
Click Here!
No Avoya Fees on Cruises or Tours. Book, change, or cancel without paying any Avoya fees. Plus, our Low Price Guarantee! No Avoya Fees on Cruises or Tours.
Click Here!
17-Night Caribbean
Cruise
Departs
Boston, Massachusetts
Sailing
Oct 22 - Nov 8, 2027
Windstar Cruises - Star Pride
Prices from
$4,689
17-Night Caribbean Cruise
Windstar Cruises -
Star Pride
Speak To A Vacation Planner
1-888-447-8459
1-888-447-8459
Unlock Avoya Member pricing for free to see if you qualify for special deals.
Cruise prices are constantly changing click here to get live pricing.
Oceanview
From
$4,689
Balcony
From
$7,109
Suite
From
$9,589
Cruise Itinerary
Departs
Boston, Massachusetts
Sailing
Oct 22 - Nov 8, 2027
Day 1
Oct 22
Boston
Massachusetts, United States
Departs
5:00PM
Day 2
Oct 23
At Sea
Day 3
Oct 24
At Sea
Day 4
Oct 25
Hamilton
Bermuda
Arrives
8:45AM
Day 5
Oct 26
Hamilton
Bermuda
Departs
7:00AM
Saint George's
Bermuda
Arrives
10:00AM
Day 6
Oct 27
Saint George's
Bermuda
Departs
12:00AM
Day 7
Oct 28
At Sea
Day 8
Oct 29
At Sea
Day 9
Oct 30
Gustavia
Saint Barthélemy, France
Arrives
10:00AM
|
Departs
10:00PM
Day 10
Oct 31
Prickly Pear
British Virgin Islands
Arrives
8:00AM
|
Departs
6:00PM
Day 11
Nov 1
San Juan
Puerto Rico, United States
Arrives
7:00AM
|
Departs
7:00PM
Day 12
Nov 2
Cruz Bay
St. John, United States Virgin Islands
Arrives
8:00AM
|
Departs
6:00PM
Day 13
Nov 3
Basseterre
St. Kitts, St. Kitts And Nevis
Arrives
8:00AM
|
Departs
5:00PM
Day 14
Nov 4
Gustavia
Saint Barthélemy, France
Arrives
7:00AM
|
Departs
10:00PM
Day 15
Nov 5
Philipsburg
Sint Maarten
Arrives
8:00AM
|
Departs
10:00PM
Day 16
Nov 6
Great Harbour
Jost Van Dyke, British Virgin Islands
Arrives
9:00AM
|
Departs
10:00PM
Day 17
Nov 7
Prickly Pear
British Virgin Islands
Arrives
8:00AM
|
Departs
5:00PM
Day 18
Nov 8
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 8 months ago by
Steffenie
Cruise Date:
07/21/2025
Destination:
Europe
Reviewed 8 months ago by
Peter
Cruise Date:
03/01/2025
Destination:
Panama Canal
Reviewed about 1 year ago by
David
“Honeymoon ”
Cruise Date:
02/08/2025
Destination:
Caribbean
Reviewed about 1 year ago by
Jeramiah
“Perfect 1st Cruise”
Cruise Date:
11/09/2024
Destination:
Caribbean
Reviewed over 1 year ago by
Paul