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Lipari or Stromboli or both? Then Ragusa

We are 5 active seniors taking the Best of Sicily tour Oct 4-14, 2020 (I like to start planning early). After the tour, we are thinking about spending about 5 days together on Lipari and/or Stromboli. I think we are all fit enough to hike up the Stromboli volcano (the least fit of us can walk for 8 miles in a day with you think this is reasonable for us to try?).

I was wondering if we should spend more than one night on Stromboli? How many days on Lipari? We like to travel slow, with walks, cafes, scenery, good food. I thought we would go from Catania to Stromboli (via Milazzo), stay one or two nights, then on to Lipari. Is this the best idea? I would love to hear of any places you loved staying at either location.

After that we are splitting up, and my husband and I will go to Ragusa for about 5-7 days. We will do some day trips from there. We prefer public transportation, although we will drive if that is much more logical. Any fantastic places to stay there (not more than about $100 per night).

Thanks in advance for any help. Donna

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