1. Home
  2. Cruise Lines
  3. Windstar Cruises
  4. Windstar Cruises Cruise Reviews

6 Windstar San Juan Cruise Reviews

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 star pride is run down. ... Read More
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 star pride is run down. They run the engine so hard at night we can’t sleep because our bed shakes so bad. Not rocking of the boat or poor weather but engine rattling that makes your teeth chatter. Our shower has a back flow issue and we come back to find it filled with mearky water even when we haven’t been using it. The worst part is that the cruise is full of drunk rude and rowdy teenagers. They will keep serving the 16 year olds alcohol as long as the parents say it’s ok. But the parents don’t watch them and let them have the run of the ship. I didn’t pay $2000pp for the spring break in Tijuana experience. If I wanted that I’d go on a cheaper large cruse. This makes it a terrible cruse for couples dealing a quite nice experience. Communication with the crew is poor. Many of them don’t speak much English. I also get the feeling many of them are unhappy and probably live in terrible conditions from our interactions. The excursions are really disappointing for the money. We landed in Monserrat and they didn’t tell us until the night before there is no was of getting around the island and nothing to do unless you had booked one of the booked out excursions. We paid $100 per person to book the last remaining activity and it was just a drive to a place where you can see a few posters explaining the volcano and watch a 30 minute video. You couldn’t even see anything else. Then you get driven to a very small garden and told it’s another $10 to go in. The other “snokeling” excursion at St. Thomas was just a booze cruse. The boat is crowded and eating onboard for breakfast and lunch is fine because it’s a buffet but dinner is very slow. We wait on average an hour for our entrees. My husband has a special diet due to a very serious health condition but the crew we interact with don’t have strong enough English to understand what he needs. They run out of things constantly. Imagine being on a cruise where you can’t get any olive oil, only dressings with sugar on your salad. We tried ordering inadvance but it does no good. He still gets the wrong things when it comes time for dinner. Also it’s very hard to eat healthy on board we’ve found a lot of things have corn starch in them. The food it’s self is still pretty good for someone with no dietary needs. Read Less
Sail Date December 2018
First - Windstar engages in flat out False Advertising (in our case -$200 in ship board credits per passenger). They were given ample opportunity to make this right and simply could not find a way to make it right. First - and last - ... Read More
First - Windstar engages in flat out False Advertising (in our case -$200 in ship board credits per passenger). They were given ample opportunity to make this right and simply could not find a way to make it right. First - and last - time Windstar customer and they couldn’t care less. Business must be great when you can alienate new customers so easily Second - communications are horrendous. In the above issue it was raised with an officer - the top guy in charge of the hotel side of things - he said he would fix it. He didn’t and we never talked to him again. This on a ship that was maybe 75% full ( 150 people). Issues were raised post cruise with HQ and the email response was that we would hear back in 1 week - that was two weeks ago. crickets - chirp, chirp, chirp. We’ve heard zip Third - ship issues -our room was never adequately supplied with AC. Issue was raised on day 1 - never really fixed but I think it was an underlying operational issue. The front 1/3 of the ship was noticeably warmer than elsewhere. Most of the trip it was tolerable to barely intolerable. The last two nights it was flat out intolerable. On other sites, I’ve seen posts questioning the financial viablity of Windstar and I am beginning to think that may be the issue. It is a big world and there are a lot of small ship cruise operators. In the future, I am going to try Windstars competitors. I will not travel with Windstar again and I will share my experience with all my friends looking for small ship cruises. Oh - the shipboard crew -absolutely fantastic! To bad they lack the management and leadership they deserve. Read Less
Sail Date December 2017
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, the better the ... Read More
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, the better the attitude. Everyone wearing an officer costume seemed to have a poor attitude or just did not really care. Never seen anything like that before. The small ship was expected to be a plus, with only 200 guests, but the captain chose to run slowly on only one engine and the ship pitched all night. Many guests got seasick and Dramamine was the number one discussion on deck. Food was sometimes good and sometimes not so great. Windstar has two charges which are not known before boarding. First, no wine or alcohol is included - it is $650 per cabin - usually we expect to upgrade to premiums for a fee. No problem with that, but should be known. 2nd, there is an $84 per person additional charge for "tips". That is just additional ticket charge and does not change the pay of servicers. We tipped maids, waiters and other help - unfortunately most guests think the tip charge is really tipping. To me that is just Windstar being dishonest. Read Less
Sail Date December 2016
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 wait for shuttle to ... Read More
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 wait for shuttle to airport where two planes were chartered to take us to St. Marteen. A cruise that was supposed to embark at 6pm was clearly not going to start for many hours. The cruise line gave us all a $150 credit for the inconvenience - which was completely inadequate for the late start, extra flight and confusion. Charter on Miami Air wasn't prepared for us when we arrived. long lines in airport - which seemed ridiculous since Windstar knew in advance who was on the plane THEY chartered. Plane left for St. Marteen late and the two people from Windstar did nothing. We arrived in St. Marteen and amateur hour continued. We arrived at cruise terminal and NO ONE from Windstar met the the bus - so the bus driver kept us on board. By now it was after 10pm and we were sitting on a bus in a closed cruise terminal. We finally boarded and filled out paperwork. Why didn't they give us paperwork in San Juan? We were captive for 8 hours already (boarding was supposed to open at 1pm) - but now we were doing routine paperwork. We got to our cabin around 11pm. We went to bar and learned that drinks were free - but there was no announcement at check in. Give free drinks - tell no one to reduce expense. Great strategy! They extended free drinks into 2nd day of cruise with limited communication. On second day we attend Captain's briefing. He announced that this was his last cruise before vacation.......clearly his mind was elsewhere and his "I'm going home" attitude spilled onto crew. There was a persistent and often shocking lack of attention to detail in every aspect of service. I blame the Captain and his senior staff. Around 2am we wondered why the ship was still in port and learned that they were waiting for emergency batteries. Why didn't Windstar communicate anything to the passengers? Was there a mechanical issue with ship all along - and the paperwork story was just a smoke screen? the change in embarkation port shifted the first two days of the itinerary. They made little effort to tell people "excursions planned for Sunday are now on Saturday and excursions for Saturday are now on Sunday".....no announcements. No changes to the tickets. Nothing. So Saturday was a scramble since we didn't sail until well after 3am after having got on board very later. On Sunday, we went to Antigua a day later than planned and learned that basically 90% of everything on port was closed on Sunday. So this stop was a complete waste of time. We went to the watersports dock one day and floated behind ship on water mat. A Zodiac from the ship was hauling in a broken sail boat and apparently didn't see us in the water. The Zodiac ran over the mat and spilled my wife and I off the mat - which was very dangerous to say the least. Room service was comical. After 3 wrong orders we gave up ordering things in the room. Casino had exactly one blackjack table and one poker table.....and exactly one dealer. So basically one game at a time. There was also supposed to be a Roulette wheel but there wasn't one. Slots and one table game at a time......the ship again failed to plan. The spa booked up very quickly - again, very few workers. To their credit, the spa didn't spend the entire treatment trying to sell lotions and potions like on most cruise lines. The ship directory in room was obsolete. None of the phone numbers were correct - so we had to call operator. Leaving ship was just as bad. We were told to be at gangway at 7:30am. They let us off at 7:50am with no explanation of delay. They didn't have enough shuttles to airport (mind you, we all had to declare where we were going on Wednesday so they had an accurate count of the people going to airport) So we stood outside an hour. Then, when the shuttle arrived it couldn't fit everyone's luggage in back - so they filled the aisle with bags. Good thing there wasn't an accident because no one could get to door through the stack of bags. I am sure that I am leaving off lots of details. For a supposedly "high end" private yacht we got impression that they never sailed before. There was limited planning and poor execution in every aspect of service. We won't sail Windstar again Read Less
Sail Date December 2016
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 mistake as the first we ... Read More
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 mistake as the first we knew that the itinerary had changed was when we arrived at Muelle1 (Pier #1) in San Juan at 1:10pm (boarding was at 1:00pm) and there was NO SHIP! I called the main office in Seattle who told me there was a paperwork problem and to go to the Sheraton in Old San Juan to meet some Windstar reps. The kind taxi driver took us about 50 yards to that Sheraton, where the bellmen told him the Windstar people had left and were probably at Muelle 4. He then drove us over to Muelle 4 where two local Windstar people handed us a sheet of paper explaining the change and claiming that the "Vacation Planner team in Seattle contacted all guests and their travel agents to advise of this change"...well, we found out on returning home that they had sent out an email the previous day when we were already in transit. They should know that communication has not occurred until confirmation has been received and when traveling not everyone has access to email. Anyway, the two reps at Muelle 4 told us to go to the Sheraton Convention Center (not the one Seattle had just directed us to) to arrange to get on one of the two charter planes to Sint Maarten. The long suffering taxi driver did just that and we found the Windstar reps in a little office. They advised that we were assigned to the 7:30pm charter and the bus for that would leave at 4:30pm. I expressed my concern at the lack of communication, to which the response was to say that "Mister Ulf" would be along shortly and to take it up with him. Mister Ulf (apparently the customer service manager for the cruise, Ulf Rademaker) duly arrived and when one of the other prospective passengers expressed concern that we would not be on board until very late and whether there were any plans for providing dinner told them "Don't worry, we won't let you go to bed hungry" and proceeded to bury his nose in a laptop. Windstar had provided a "hospitality room", but this had obviously been set up for lunch for the first charter plane and by 2:15pm consisted of unrefrigerated cold cuts and stale bread...really sanitary. When 4:30 rolled around, a scrum formed to get on the one overloaded minibus, leaving some to be abandoned waiting for a replacement minibus. Checkin was not bad to the Miami Air charter, but proceeded very slowly. Then there was a 2-hour wait for the departure time during which most of the passengers found something to eat at their own expense at the airport. Meanwhile Mister Ulf arrived in the departure area and spent his time in conversation with other crew members, avoiding the passengers seemingly at all costs. Arrival and Immigration in Sint Maarten were surprisingly rapid and we were then loaded on another bus to get to the ship. After a long scenic trip across the island, we arrived at the cruise terminal to find that there was nobody to meet us and escort us in and down the pier. Someone finally turned up and escorted us to the ship where we had to go through the usual check-in, which was overloaded as everyone was arriving at once. The customary safety drill was then held, and by the time that was over it was 11:00pm. I asked reception if there was any food available, and they told us that the dining room would be open for another 15 minutes. It was in the dining room that we found out that drinks were being comped for the rest of the day...more good communication, they could have told everyone that at check-in! Now we were finally on board. The itinerary was supposed to be San Juan - Culebra - St Barths - Montserrat - St Maarten - Jost Van Dyke - Virgin Gorda - San Juan. What we got was St Maarten - St Barths - Antigua - Montserrat - St Maarten (again) - Jost Van Dyke - Virgin Gorda - San Juan. Missing Culebra was a disappointment but understandable in the circumstances and moving St Barths from Sunday to Saturday was probably a plus as most of it is closed on a Sunday. Ports in order visited: St Barths - we have always like this island and Saturday was better than Sunday would have been. You are tendered ashore here and we noticed that the tender crews seemed poorly skilled at handling the twin-engined tenders compared to other small ships we have been on. They appeared to be being trained by one of the officers, but did not seem to be paying much attention. The drinks were still being comped on this day...not that any notice was given other than one brief announcement. Antigua - added because of the changed itinerary. This was a docked location, so no tender issues. On a previous visit, we had been anchored off Falmouth near Nelson's Dockyard in the south of the island and that would have been much nicer and less exposed to the incessant "marketing" at the cruise pier in St Johns. Montserrat - If you don't take a tour here (we didn't) this was pretty boring. Sint Maarten - (again) - tied up to the pier, so access is good. The toilets on the ship went out of action for about an hour, but they appeared to be pumping out the black water tanks at the time, so we assumed that was the reason (more on this later). Sint Maarten seems to be all about shopping. Jost Van Dyke - not much to do here as a tender access port. Unfortunately, the toilets went out of action again for the whole ship at about 10:00am. After lunch, they were still out of action and when my wife asked if there was any progress or projected fix was told about 2 more hours. She remarked that it might be a good idea to have an announcement, the reception staff commented that that was a decision "for the stripes"...amazingly within a few minutes the captain made an announcement that it would be about 2 more hours (it was a bit less in the end)...but why was it not announced right up front instead of just locking all the public access toilets? More non-communication. Virgin Gorda - This is the beach party location that is also used by the older Windstar ships and by Sea Dream. The food at the beach was good, but the 200+ passengers seemed to overload the facilities and the sand fleas and mosquitoes were voracious. Unfortunately, the tender service did not extend to the Bitter End Yacht Club. San Juan - Disembarkation was delayed, presumably by customs/immigration..again no announcements as to what was going on. We were on a late flight, but would have been pretty anxious if we had been on the first batch of passengers with an early flight. Food on the whole was OK, but appeared to "benefit' from the Indian chef's native foods - almost all the menus had a curry flavor choice included. Breakfasts were OK, but the setup of the buffet is not conducive to good flow of people. Lunch is quite limited and the one time I ordered a hamburger, I found out after 25 minutes that the grill was broken and it would take another 10 minutes to arrive...again communicate. The main dining room was pleasant and we had no troubles with being assigned a 2-spot if we wanted it. Wine service was slow (understaffed) and not that helpful. The one night of the deck BBQ was rained out and set up in the dining room instead...the best food of the cruise! We eat in the alternative restaurant (Candles) one night; this is set up as a steakhouse and tries to serve that way. The food was good, but the service was amateurish, with long waits between the main plate arriving and sauces and sides appearing...and one of the sides appeared wrong and cold. Entertainment was two different singing acts, both quite pleasant and one very accomplished (Vice Versa) and to our taste. Service was in general mediocre - not for want of trying by the staff who really wanted to please, but they just seemed to be lacking in supervision, and the supervisors appeared to be taking more time to preen around in their uniforms than pay attention to the actions of their staffs. We had booked on this Windstar (we had been on Wind Spirit many years before) to see how it compares to SeaDream, acknowledging the lower price and fewer inclusions. Unfortunately, the lower price point does not in our minds compensate for the poor performance of the company in communication and supervision, so, absent a compelling itinerary we are unlikely to be back. It's a shame as the ship is a nice size, the cabin comfortable and the low-key entertainment was a pleasant addition. Read Less
Sail Date December 2016
If not for the crew, food and beverage servers, and our room steward, our first Windstar "Luxury Cruising" experience would have been a complete disappointment. With that said, my wife and I decided on the Windstar Legend. We ... Read More
If not for the crew, food and beverage servers, and our room steward, our first Windstar "Luxury Cruising" experience would have been a complete disappointment. With that said, my wife and I decided on the Windstar Legend. We were more than excited to board such a "luxury" style yacht for this very special vacation. As we boarded, we were greeted by Captain Richard and Hotel Manager Calvin, which was a very nice personal touch. Our cabin was pleasant and comfortable. We began to walk around the exterior of the ship, and found it not welcoming at all. It seemed like the ship was closed down. There was no water in the pool, lounge chairs were stacked up, and no music was playing. We walked further and began to get a common theme that the Windstar Legend was far from Luxury but was a very weathered yacht. My wife and I looked at each other and I actually asked her if we just made a big mistake and if she wanted to get off before it sailed. We are optimistic people so we went with it... We met amazing people, and the staff could not have done more for us. They were great. Windstar marketing and advertising manager should receive a raise because what is portrayed on the videos and the website is a far cry from reality. The broken ice cream machine/freezer, the aged tenders, the lack of watersports, which was a very big attraction for us, and inflatable zodiacs were completely unacceptable and embarrassing. Tenders were constantly broken, and the drivers were incapable of controlling a tender frequently slamming them into the platforms the days they were in operation. There was actually a day when we had no functioning tenders at all, and elderly passengers with canes were taking the zodiacs back to the ship. This was not safe, and as a result, I was helping to get them on and off the boat. It was ridiculous. Most passengers on the ship felt the same. I heard the couple staying in the owners suite did not have Air conditioning in their room for 3 days and asked to get off the ship. The reality of the situation is that the Windstar Company should be embarrassed to provide their employees with such old broken down equipment. The next consideration for the Legend might be providing the employees with the proper resources to do their jobs. As I stated previously, we had a great time on our Honeymoon, but it was only because of the staff and the wonderful people we met. In fairness to Windstar, I must mention we did voice our concerns with them after returning home and were compensated for our dissapointment. Read Less
Sail Date November 2015
Already Booked?

Get to know who you’ll be sailing with

Find a Cruise

Easily compare prices from multiple sites with one click