Thanks. I was thinking about europe (Spain and/or Portugal).
I'm heading to Portugal for 3 weeks. It's budget friendly compared to most other Western European destinations. Kosher food is only available in Lisbon and Porto, and you won't have what to do for 3 weeks if you stick to only those two areas.
My plan is to cover Mainland Portugal + Madeira. My trip consists of 1) history (castles and pre-inquisition Jewish communities), 2) nature such as hiking, beaches, and wine country, and 3) cities such as Lisbon and Porto, as well as a few smaller ones.
I originally planned on doing 5 weeks with the last 2 weeks in Azores, but I have a scheduling conflict so I was forced to cut it short.
I have an extensive itinerary worked out with a lot of information that the local Jewish communities were kind enough to share, so feel free to PM me if you want to know more.