We flew to San Juan on the morning of our trip since it wasn't far so I can't comment on local hotels. The ship does dock in Old San Juan which is close enough to walk around a little if you have time and is a pretty place with lots of history. Boarding was very easy and relaxed.
All of the food we had was good to excellent on this trip. We dined in all of the restaurants more than once including Le Champagne. My daughter really enjoyed the Hot Rocks grill by the pool at night. I thought is was fun and a very nice casual experience for days that we were a little tired from all of the sun and fun. The main dining room was nice, not too large but not crowded, and formal nights were beautiful as many guests did choose to dress up on this cruise. Here's the part where I say that Silversea is definitely a bit more formal on all evenings than some of the larger ships so keep that in mind if you are not someone who likes to dress for dinner and settle in for several courses. There are "informal" evenings but this is still upscale casual attire expected. Personally I enjoy this type of dress code but I realize it's not for everyone.
I think the good food was made even better by the staff. I felt a cohesiveness on this ship that is sometimes lacking in the service industry. It really seemed like they were all working together and truly enjoyed making us happy.
Cabin was nice but I believe we were on deck 7 under the pool area. Not a problem most of the time but we did encounter a bit of noise from the moving of deck chairs and closing of the restaurant that occurs late at night and again more moving early in the morning. The advantage to deck 7 was that the La Terrazza restaurant was right at the end of the hall so breakfast was easy to get to. Veranda Suites have a decent size walk in closet, a separate sitting area, and a small veranda only large enough for the two deck chairs and small table. The bathrooms on the Wind are a bit smaller than the other Silversea ships but still not tiny.