I downsized by selling my 10 acre property/house first and reducing all my belongings to what would fit in my car trunk plus two boxes at my daughter's house. If I had known when and where I would wind up, I would have put some stuff in storage, but my original plan was to travel for a year or two.
Then six months of travel later, I found a place I could afford (cost less than half of what I got from selling my house) that checked all the boxes for me (even boxes I didn't know I should have) -- condo in a high rise with an elevator in a 55+ gated community with walking paths, trees, wildlife, clubhouses (aka private senior centers), walk-able to grocery and doctors/dentists, lots of options for activities for seniors of all ages, and with good public transportation to a big city.
I've been here over two years now and I still really love it.