if you want to go to Maderia - then funchal is the place to stay, and the old town at that...
we stayed in this little street (twice).. Google Maps Find local businesses, view maps and get driving directions in Google Maps. www.google.com
plenty of cheap restsurants around...
We did prague last January and it was great. We have ended up booking Krakow, Rome & Athens but at the same time we are combining Athens with 4 days in Rhodes.