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Windstar San Juan Cruise Reviews

Windstar

Ship

Destination

San Juan

Traveler rating

34

6

7

6

2

Cruise type

23

Romantic Cruises

16

5

Repositioning Cruises

5

3

55 Windstar San Juan Cruise Reviews

CanadianKate

1 Review Written

5 Helpful Votes

First Windstar Cruise, A T-Atl

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This cruise was thrust upon us. We had booked a mid-Feb cruise on the stretched Star Breeze from BCN to MIA but construction delays cancelled that a few days before Christmas. Since we were within 60 days of ...

Sail Date February 2020

Redtravel

25 Reviews Written

58 Helpful Votes

Once more before the stretch

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Two years ago Windstar announced the plan to stretch the Star ships increasing the guest capacity from 210 guests to 310 guests. We love the small size and hope that the increase in size doesn’t change the ...

Sail Date January 2020

alanxfox

1 Review Written

1 Helpful Vote

Wonderful cruise, with a few glitches

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Caribbean - All

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 ...

Sail Date November 2019

Misty Morning

3 Reviews Written

36 Helpful Votes

Great Back-to-Back Caribbean Cruise

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Caribbean - All

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 ...

Sail Date November 2019

walker_michelle

3 Reviews Written

3 Helpful Votes

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

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Caribbean - All

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 ...

Sail Date November 2019

ScottLewis

1 Review Written

2 Helpful Votes

Truly first class experience

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Caribbean - All

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 ...

Sail Date March 2019

russg140

22 Reviews Written

79 Helpful Votes

You get what you pay for, just manage your expectations

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Having done this exact cruise last year, albeit a little later in the Spring, and enjoyed it so much we booked it again when offered. In full disclosure we got an AMAZING deal that we couldn't pass up. The ...

Sail Date March 2019

mickeyarthur

2 Reviews Written

7 Helpful Votes

14 days, so,so, Eastern Caribbean cruise

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Caribbean - Eastern

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 ...

Sail Date November 2018

Amandahr

1 Review Written

9 Helpful Votes

Avoid the Star Pride.

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Caribbean - All

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 ...

Sail Date December 2018

Fridaynightlights

3 Reviews Written

7 Helpful Votes

A nice change from the ordinary cruise!

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Caribbean - All

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 ...

Sail Date November 2018

JaniLuvs2Travel

1 Review Written

4 Helpful Votes

Star Pride Caribbean

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Caribbean - All

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 ...

Sail Date November 2018

russg140

22 Reviews Written

79 Helpful Votes

Very good with a few hiccups

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We got an offer from WS for the Eastbound TA as a prior cruiser and it truly was an offer we couldn't refuse. We had always wanted to try the power yachts (or as someone I know calls them "baby Seaborns" since the ...

Sail Date April 2018

Ormond Beach 321

6 Reviews Written

5 Helpful Votes

Lots of things right about this trip

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We wanted to try a transAtlantic cruise and the 13-day trip from San Juan to Lisbon seemed perfect. We had delightful weather the first 10 days, interesting weather the last three. Our bad that we didn't realize ...

Sail Date April 2018

mss289r

1 Review Written

2 Helpful Votes

Atlantic Crossing

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Great trip! Thirteen days at sea and away from chaos of USA. The crew were phenomenal and really care about customer service. Beautiful suite with Juliet balcony. It was really nice to sleep with door open and the ...

Sail Date April 2018

jennlynnprin

1 Review Written

2 Helpful Votes

Fabulous Cruise I Never Wanted to End!

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Caribbean - All

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 ...

Sail Date January 2018

CoralReef

5 Reviews Written

5 Helpful Votes

Good cruise on a bad cruiseline

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Caribbean - All

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 ...

Sail Date February 2018

SteamboatWillie118

11 Reviews Written

68 Helpful Votes

One of our favorites! (not for everyone)

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Caribbean - All

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 ...

Sail Date March 2018

FLCC1234

1 Review Written

6 Helpful Votes

Beautiful room, fantastic food, great itinerary

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Caribbean - All

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 ...

Sail Date December 2017

Astalarasta

1 Review Written

8 Helpful Votes

Star Pride- San Juan to San Juan

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Caribbean - All

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 ...

Sail Date December 2017

GrandmaP2

2 Reviews Written

3 Helpful Votes

The employees and customer service make this cruise excellent

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Caribbean - All

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 ...

Sail Date December 2017

Konamaui247

1 Review Written

4 Helpful Votes

Beware Spring Break

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Caribbean - All

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. ...

Sail Date March 2017

SkygirlSue

1 Review Written

7 Helpful Votes

Fabulous Ocean Crossing!

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I chose this cruise because a) I am hooked on Windstar cruises and b) I wanted to see what an ocean crossing is like. Wow, wow and wow! I loved this adventure....14 days on the open sea, whale and dolphin ...

Sail Date April 2017

Robert_fromthe_South

1 Review Written

8 Helpful Votes

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

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Caribbean - All

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, ...

Sail Date January 2017

LuvDCaribbean

9 Reviews Written

38 Helpful Votes

Another Spectacular Week on Windstar

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Caribbean - All

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 ...

Sail Date March 2017

SteveThe Travler

1 Review Written

5 Helpful Votes

Cruising The B.V.I.on Star legend

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Caribbean - All

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 ...

Sail Date January 2017

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