Traveling from Florence to Italy in May and leaving 1 day/night for castle stay outside of Florence/Tuscany. Need suggestions of castle with room accomadations, a restaurant, and wine tour on grounds.
Not sure if you will find a lot of Rick Steves' contributors who have experience with that type of accommodations. They are not for the frugal traveler.
You can do some research below:
https://www.icastelli.net/en/theme-stay/stay-in-a-castle/italy/tuscany
http://www.residenzedepoca.it/en/
Below are some famous ones. No direct experience, just well known to low income Tuscan people like me.
http://www.ricasoli.it/
http://castellobanfiilborgo.com/it/
http://www.castellodelnero.com/activities-it.html
http://www.castellodicasole.com/it
http://www.castigliondelbosco.com/it
http://www.castellodivelona.it/it/
http://www.castellogabbiano.it/
While not castles, I've visited the following agriturismos, both of which are wineries while on wine tours, and both have the character of renaissance palaces or grand estates. If the accommodations and food are half as good as their wines, you won't be disappointed.
http://www.principecorsini.com/en/content/villa-le-corti
Good luck.