Travel

Neil: Can you? Sure. The question is how to do it. At two nights per city, you'd be at 26 for the list of 13 locations. With about 33 days total on the ground (assuming May 8 and June 11 are travel days), well, you can add a 3rd night to 7 locations, or some such combo. I have not traveled extensively in Spain, nor been to Sicily, but I know I would never move around that much. It's exhausting and all you end up with is a list if sites you checked off. Every time you change locations you lose half a day. Your trip will be a series of packing and unpacking, hopping trains and busses, checking in-and-out. Now that I have that off my chest I'll get off my soapbox and be more pleasant. I suggest you combine your locations in Spain. Perhaps in Spain you can efficiently stay in Madrid for 4 nights and take in Toledo as a side trip. Then on to Seville for 4 nights where Jerez DeLa Frontera becomes your side trip, maybe Granada and Malaga too. Barcelona is good for 3 nights on your way to Italy. I'd ask why Turin and Milan. If you have special sights you want to see there, great. Plan your time around those but devote more time than you think you need to Venice, Rome and Florence. I'd do 3-4 nights in each, and preferably 5 in Rome. Others who have been to Sicily need to chime in, but it's like a separate country. Worth at least 5-7 nights, and that's just a start. Summary: Madrid (4), Seville (4), Barcelona (3), Turin (2), Milan (2), Venice (4), Florence (3), Rome (5), Sicily (6). That's 33 nights. Assumes you fly out of Sicily. Now plot it out with what you want to see, how much time transportation will take both between cities and to do the daytrips. Whew! Extensive trip, but you can do it with planning!

Your trip can be done but why? It would be too much for us to take on in that amount of time. We would either have the tour start in Madrid and end in Barcelona or start in Turin and end in Sicily. Looks like two trips to me but have a great time!

If your up to it - go for it. Just plan carefully so that use your time wisely. Some of these places may noly deserve 1 night while others will require 3 or 4. Some places can probably be done as day trips fron nearby cities.