We are in the process of planning our second tour in Italy to include an in-depth stay in Florence, a couple of days in Padua, a trip along the Amalfi Coast (preferably with a private driver and a night or two in a recommended town), at least a 2 week self-drive tour in Sicily, and a visit to Capri. We prefer to travel in the shoulder seasons (early or later in the year). We will be flying internationally from-to Seattle. Would appreciate ideas/recommendations for reasonable order to tour these destinations and favorite times of the year. We are retired so have no restrictions on length of trip. Thank you for your consideration.
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Hi! That’s a really ambitious and exciting itinerary—you’ve basically included some of the most diverse regions of Italy, which is amazing, but also means pacing will be key.
One thing I’ve found helpful when combining places like Florence, Amalfi Coast, Capri, and Sicily is to think less in terms of “how many cities” and more in terms of travel time vs. experience time. Italy looks small on a map, but moving between these regions can take a full half-day or more each time, especially once you factor in trains, ferries, and transfers.
If it were me, I’d try to reduce repeated long jumps and group things more smoothly:
Florence + Padua works well together in the north
Amalfi Coast + Capri is best treated as one coastal base experience
Sicily really deserves its own dedicated block because it’s quite different in feel and logistics
Also, don’t underestimate how tiring frequent hotel changes can get. Even just adding one or two “rest days” in between major moves makes the trip feel much more enjoyable.
Overall though, your list covers a great mix of culture, coast, and history—just make sure the schedule leaves room to actually enjoy each place instead of rushing through it at wa gb