No date announced yet. No English language article yet, but here is the Natalie source (edit: Anime Corner article). This announcement comes as the finale of season 1 just aired today. Synopsis for season 1 from AniList:
Lawrence is a traveling merchant selling various goods from a horse-drawn cart. One day, he arrives at a village and meets a beautiful girl with the ears and tail of an animal! Her name is Holo the Wisewolf and she brings bountiful harvests. She wishes to return to her homeland, and Lawrence offers to take her. Now, the once-lonely merchant and the once-lonely wisewolf begin their journey north.
Can you watch the original series and continue with this second season? Have been planning on watching S&W for… 10 years (oh dear), but probably don’t want to see the same story twice back-to-back. Or only watch the new version?
So, the 1st season of the remake covers books 1-4. Both seasons of the original covers 1-3 and 5. So, no, skipping the 1st season is not recommended imo. That also means the 2nd season of the remake starts with the final arc of the original. However, the remake is really close to the original. Here and there it’s a little more faithful to the books and Holo is a little more playful. So, if you watch the final arc of the 1st season, I think you should be fine, but then the 1st arc of the next season is a repeat again. I’d still recommend watching the remake in full, just to get used to the new artstyle and music.
If you’ve watched neither, then I guess the safer bet is to just watch the new one. I personally prefer the original though (for personal reasons like preferring the music and style).