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San Juan to the Caribbean Windstar Cruise Reviews

Windstar
Ship
Caribbean
San Juan

Traveler rating

Excellent

30

Very Good

4

Average

6

Poor

6

Terrible

2

Cruise type

48 San Juan to the Caribbean Windstar Cruise Reviews


Misty Morning avatar

Misty Morning

3 Reviews Written

36 Helpful Votes

Great Back-to-Back Caribbean Cruise

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Just as a bit of background, we are a Canadian couple in our mid 50’s from Montreal. This was our 13th cruise having sailed 5 times with Celebrity and now 8 times with Windstar on both the Sailing Ships and Motor ...
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Sail Date November 2019


alanxfox avatar

alanxfox

1 Review Written

1 Helpful Vote

Wonderful cruise, with a few glitches

This is basically a wonderful ship, with a few glitches. It was recently bought by Windstar and is due to a major renovation/refit in 2020, so these comments might not apply to later sailings. This is a small ...
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Sail Date November 2019


walker_michelle avatar

walker_michelle

3 Reviews Written

3 Helpful Votes

Our first Windstar cruise & would absolutely do another one. Smaller ship a plus

Windstar has only 6 ships so and they are small ships focused on going to areas the bigger ships cannot get to. While the ship itself is a little dated, it is slated for a big makeover this summer which is ...
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Sail Date November 2019


ScottLewis avatar

ScottLewis

1 Review Written

2 Helpful Votes

Truly first class experience

Our first Windstar cruise, based on a recommendation from a friend who knows that we like smart and engaging people, don't like rowdy drunk crowds, and want a genuine experience. We learned a lot and immediately ...
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Sail Date March 2019


mickeyarthur avatar

mickeyarthur

2 Reviews Written

7 Helpful Votes

14 days, so,so, Eastern Caribbean cruise

The Star Pride, food service and crew met all of our expectations and are the reason we continually pick Windstar. On board services were first class. Now for the cons: Since space is not available for a large ...
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Sail Date November 2018


Amandahr avatar

Amandahr

1 Review Written

9 Helpful Votes

Avoid the Star Pride.

I’ve been on one of windstars Mediterranean sailing cruises and it was wonderful, but the star pride Caribbean cruse has been a horrible waist of money. Not a nice experience at all. Unlike the sailing ships the ...
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Sail Date December 2018


Fridaynightlights avatar

Fridaynightlights

3 Reviews Written

7 Helpful Votes

A nice change from the ordinary cruise!

We picked this cruise for the ports, price and small ship experience. With 210 passengers it was a clear change from the 23 previous cruises we have had on nearly all the major brands, sans Carnival. The week ...
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Sail Date November 2018


JaniLuvs2Travel avatar

JaniLuvs2Travel

1 Review Written

4 Helpful Votes

Star Pride Caribbean

Embarkation is a walk right on, and too long of a wait. They have different stations to visit, port excursions, spa, drink package, etc. They take your credit card and give you your key and you are free to go to ...
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3 photos

Sail Date November 2018


jennlynnprin avatar

jennlynnprin

1 Review Written

2 Helpful Votes

Fabulous Cruise I Never Wanted to End!

We chose this cruise based on both the timeframe and the destination. Our departure port was Old San Juan, Puerto Rico, and arrived a day early to have a photo session with a photographer in Old San Juan, explore ...
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Sail Date January 2018


CoralReef avatar

CoralReef

5 Reviews Written

5 Helpful Votes

Good cruise on a bad cruiseline

This was our first small ship cruise, and we enjoyed it. The onboard experience was excellent. However, I’m not sure I would book another cruise on Windstar, due to the multiple frustrations of dealing with their ...
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Sail Date February 2018


SteamboatWillie118 avatar

SteamboatWillie118

11 Reviews Written

68 Helpful Votes

One of our favorites! (not for everyone)

For those of you who want 'the scoop' and are waffling whether to cruise on this type of ship - here's a summary: 1. Don't book if you're disabled, seriously. There's elevators, but they don't go everywhere, and ...
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Sail Date March 2018


FLCC1234 avatar

FLCC1234

1 Review Written

6 Helpful Votes

Beautiful room, fantastic food, great itinerary

Prior to this cruise I had taken maybe a dozen Caribbean cruises. I chose this cruise primarily because I had never visited its five ports of calls and secondarily because I thought that it would be a step up from ...
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Sail Date December 2017


Astalarasta avatar

Astalarasta

1 Review Written

8 Helpful Votes

Star Pride- San Juan to San Juan

We sailed round- trip from San Juan Puerto Rico on the Star Pride from 12/2/2017 to 12/9/2017. Embarkation: The port appeared to be in good shape, we arrived by cab around 1:30 PM. After clearing port ...
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Sail Date December 2017


GrandmaP2 avatar

GrandmaP2

2 Reviews Written

3 Helpful Votes

The employees and customer service make this cruise excellent

We had been on a windstar cruise nine years ago and had always wanted to go on another, but before there were no elevators and we have mobility problems on stairs and walking long distances. We had booked a regular ...
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Sail Date December 2017


Konamaui247 avatar

Konamaui247

1 Review Written

4 Helpful Votes

Beware Spring Break

Beware. Do not book this cruise over Spring Break- Caribbean. Beware of other voyages as well since Windstar apparently caters to these types of events and is oblivious to the impact on their repeat customers. ...
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Sail Date March 2017


Robert_fromthe_South avatar

Robert_fromthe_South

1 Review Written

8 Helpful Votes

Relaxed Small Ship Birthday Cruise-Just what I had hoped for!

I’m a bit late with my reviews, time got away from me… My wife and I were on the Star Legend , Windstar Cruse from January 28 - February 4, 2017. I have been on numerous cruises, Norwegian, Carnival, Disney, ...
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Sail Date January 2017


LuvDCaribbean avatar

LuvDCaribbean

9 Reviews Written

38 Helpful Votes

Another Spectacular Week on Windstar

We sailed on March 25th, from San Juan. Our 4th Windstar cruise but 1st time on the Legend. We’ve been on the “Star” once and the “Surf” twice. As always, every day was perfect except 1 – a day ...
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Sail Date March 2017


SteveThe Travler avatar

SteveThe Travler

1 Review Written

5 Helpful Votes

Cruising The B.V.I.on Star legend

We booked this cruise for the "small port" experience and the Windstar style of cruising. Also we had not been to the B.V.I. before. We had sailed once to Costa Rica with the ship Wind Star. After a long trip from ...
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Sail Date January 2017


su-arizona avatar

su-arizona

5 Reviews Written

51 Helpful Votes

Star Legend is a Real Star

The Star Legend sails in a galaxy far far away from her sister ship, the Star Pride. Windstar has done a superb job of updating the Star Legend, giving new life to an old beauty that was lacking in the Star Pride. ...
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Sail Date January 2017


Jon898 avatar

Jon898

1 Review Written

7 Helpful Votes

Lack of Communication and Poor Supervisors

This was the same cruise that dsyoung422 was on, so many comments are similar. The cruise was supposed to start in San Juan and we flew down the night before as independent travelers. I guess that was the first ...
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Sail Date December 2016


sawplayer avatar

sawplayer

1 Review Written

4 Helpful Votes

This small ship is the ONLY way to cruise!

We took this cruise to get a chance to travel with friends and not have to deal with the crowds on the giant ships. And we did have a GREAT time with our friends! With so few passengers and so many crew, you get ...
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Sail Date January 2017


JLucas2018 avatar

JLucas2018

1 Review Written

5 Helpful Votes

Staff great, officers less than good

Wanted to visit numerous islands and picked this one due to the inclusion of St. Bart's. Unfortunately, the captain decided to skip St. Bart's and go to another island instead. The lower on the staff totem poll, ...
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Sail Date December 2016


vitman avatar

vitman

1 Review Written

7 Helpful Votes

Amazing ports, great crew, and the ease of a luxurious small ship

Our main reason for selecting the Windstar Star Legend was the itinerary of generally smaller out of the way ports. We wanted to visit some small islands that we have not had the chance to explore during previous ...
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Sail Date December 2016


dsyoung422 avatar

dsyoung422

1 Review Written

12 Helpful Votes

Amateur hour from start to finish

Cruise was supposed to depart from San Juan on 12/9 but the cruise line didn't file proper paperwork with port authority so ship went to St Marteen. Passengers were told to meet at Sheraton hotel in San Juan and ...
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Sail Date December 2016


suzeshoes avatar

suzeshoes

4 Reviews Written

96 Helpful Votes

Best Way to Yacht!

We were apprehensive after hearing reports regarding the tenders and the bottled water and the condition of the Star Legend. But we were happily and pleasantly surprised to enjoy a wonderful sailing last week on ...
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Sail Date January 2016


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