Doug, I'm not Karen, but I was there last year (Voyager), and it couldn't have been much, it is only like a 5 minute climb. Much preferable to the donkey ride I did about 10-12 years ago on a land trip. The donkeys hung to the left side of the path and I often scrapped my leg on the wall, they stunk, and they vie with each other for position (like trying to nose in from behind the one you are riding). We certainly laughed alot, though! This was 6 women who had no idea, and we were ready for whatever! I think you guys just need 2 cab drivers, one to get you to either Oia or Akrotiri in the a.m., return to Fira for lunch at a wonderful restaurant overlooking the sea and some time to stroll the streets, and then go to the other in the afternoon. For the afternoon site, just be sure you make the ship, as it is off season, and there are not so many of cabs at either end of the island. I did not do the winery tour, but loved Karen's description...it sounds like one I'd like to miss, after the special one I had in Beaune many years ago at Louis Jadot! Did you know that today T&L released its World Best ratings, and Santorini was the #1 Island in Europe?