We went on this tour as a "blind date" with 8 other people from Cruise Critic. We had basically the same group again for 2 other tours and despite the misgivings of whether it would work or not, on this occasion everyone got along really well and it was definitely the better option over a ship's tour.
Island Tour Rating:
We were to meet Dimitri at 3pm, however we got a very early tender and were able to get to the top at 2.30 - our group leader rang ahead and Dimitri was there not too long after us. We had a good overview tour of the whole island which included Santos winery, Ana's homemade stall, the Black sand beach and of course Oia. We didn't see too much of Fira at the start as we took off more or less straight away.
One of our group was an older lady not as sure on her feet and there was a bit of a steep walk down stairs to where the van was parked, but she managed with help. Be aware that all the streets are uneven and there are many stairs everywhere.
Dimitri was very affable and gave good local inside information on the workings of the island. The van was very new, air-conditioned and extremely comfortable.
We felt though that we probably spent a bit too much time in getting to Oia which is after all the highlight of the trip. It was already getting dark when we got there and whilst we were wanting to see the sunset, it would have been good to have arrived a little earlier to get some brighter pictures as well.
The only thing we would change would be to request more time in Oia. We then returned to Fira but not really with any time to see it or do any shopping before going back to the ship. Would like to have spent more time in both places.
If you are coming via cruise ship, try your best to get one of the early tenders. Dimitri's wife had another group and they didn't start their tour until a couple of hours after us as they got a much later tender off the ship. They basically went straight to Oia as there was no time for anything else, at least I assume so as they were already there when we arrived.