We chose this cruise on the Star Pride because the itinerary included some of our favorite Caribbean islands (leaving and returning from San Juan): St. Thomas, St. Barths, Montserrat, St. Martin, Jost Van Dyke, and Virgin Gorda (Prickly Pear Island). Unfortunately, our cruise missed Montserrat and St. Martin due to weather which was frustrating. Embarkation and disembarkation in San Juan was very quick and easy. It is only a 15 minute Uber or taxi ride from the San Juan airport to the dock. We flew in on the day of our cruise (not something you should do but we did not have the time to fly in the day before) but we had no problem and were not particularly worried since the ship did not sail until 10 pm (very convenient). On disembarkation day, we flew out of San Juan on a 10:24 am flight. Originally, we thought this was too tight but we were able to get off the ship at 7:15am and were at the airport by 7:45am so we changed our flight to an earlier one. We were able to do this because we elected the carry your bags off the ship yourself option (we did but plenty of people got off the ship at the same time with huge bags and the staff helped them carry them off which was lovely).
This was our first time on Windstar and we thought overall it was a very good "budget luxury" line. We have been fortunate to have cruised on every type of cruise ship (big, medium, and very small) and cruise line from luxury to very economical (Sea Dream Yacht Club, Regent, Oceania, Star Clippers, Costa, Princess, HAL, Royal Caribbean, Norwegian, Carnival etc.). We prefer small and mid size ships because the most important thing for us is a great itinerary. The smaller ships tend to go to the better and less touristy ports. We are not cruise snobs and have enjoyed almost every cruise we have been on.
We sailed on the Pride after the "stretch" and we can only imagine that the ship must have felt much less crowded with 100 fewer passengers. While we appreciated the modern bathrooms and beautifully updated common spaces, the ship did at times feel crowded (we had 289 passengers on our sailing) particularly in the Amphora (main) dining room and in Veranda (the buffet restaurant). Candles was our favorite (beautiful setting, excellent food and service). We were disappointed we could only eat there one night. Our least favorite dining experience was the on deck "signature" buffet dinner (it was your only choice that night because all the other restaurants were closed). The lines for the food in the buffet were so long. It felt crowded and terrible because everyone was trying to eat a the same time. Next time, we would skip it and just order room service. I wish they would leave the speciality restaurants open on this night.
Our first cabin (450...oceanview suite s1) which was a handicapped accessible cabin (we did not chose a handicapped cabin...we were assigned it) on the fourth floor in the back of the ship was possibly the worst cabin we have ever experienced on a cruise ship. It was so incredibly loud (we assume from the engine) and the handicapped bathroom was very small and had no door or shower curtain on the shower so the bathroom got very wet when anyone took a shower. We were unable to sleep the first night because of the noise, but fortunately reception was very kind and helpful in moving us to cabin 421 (same category of cabin) the next day. This cabin was in the middle of the ship and was so much quieter!! The shower had a door which was a relief. Great water pressure in the newly remodeled bathroom. Like our first cabin, it had a picture window and was not in the new stretch part of the ship. This meant our bed was near the door not the window. I would have preferred the newer layout. As people have commented, the beds are comfortable with great bed linens but incredibly low (odd for a cruise ship) and the furniture in our cabin was old and tired. The lack of UBS ports or even a plug near the bedside tables was frustrating because we could not leave our phones next to our bed at night. We did appreciate the cabin's large size and loved that there was plenty of storage space.