I have not been on that cruise as of yet but I have taken 7 cruises on Windstar and am about to book another. I’ve taken a Baltic cruise on Silversea on their largest ship which I think holds 600 people. You are comparing yacht to yacht for this cruise as Windstar sailing ships do not do this route.
Here are a few differences/ similarities:
Silverseas:
-a true luxury ship complete with room butlers.not that you really need a room butler …
-definitely more formal with some venues requiring a jacket. It is a ship that you will want to bring a cocktail dress or two.
-Staff is amazing
-With the larger ship (600 capacity ) there were numerous dining venues and areas to hang out. A few required an extra cost - all the meals were excellent though. They do have smaller ships (300 capacity?) so I can’t speak to those.
-food is amazing
-alcoholic drinks are included in cost - nice variety of wines to choose from
- it’s a very expensive cruise line. We got an amazing deal that included airfare with a very reasonable cost for an upgrade to business class and enough on board credits to cover our excursions
-I’d go back in a hot minute but it’s usually really expensive.
-I was afraid that with the more formal atmosphere it would be a ‘stuffy’ less friendly feel but that was not the case.
- we went in a 7 day cruise and I really wished we had signed up for a longer cruise. I did not want to leave.
Windstar:
- it is a really nice line but is not the true ‘luxury’ class.
- the sailing ships are great - particularly in the Caribbean where they get to sail a lot. I have only been on one of their yacht once and it was before they were refurbished. T (which were purchased from Seaborne- another luxury line)
- The atmosphere is casual, relaxed, friendly. No need for jackets, ties, cocktail dresses. Think country club casual with shirts, polos pants for men, and sundresses/ casual dresses or nice top & pants for women at night.
- wonderful friendly staff
- very good food, better than most of the big cruise lines - Princess etc.
- smaller ports to explore that big commercial ships cannot get into - might be true of the smaller Silversea ships, I’m not sure.
The choice for me it would come down to cost ….if pretty close I’d go for Silversea