At that time of year, I would usually say start in the north for weather purposes and work your way

How we use your email Fodor's may use your e-mail address royal carribean cruises to ensenada to send you relevant information on site updates, account changes, and offers. For more information about your privacy and protection, please review our full Privacy Policy .
Personally, I would go directly to Venice, as IMO it is the easiest city for recovering from jetlag since you are walking everywhere and there are no vehicles. I would then go to CT, to avoid the possibility royal carribean cruises to ensenada of bad weather further into October. Then Florence, then Rome.
It takes almost a full day to get from Venice to CT, (breakfast, pack, check out of hotel, get to train station, 6-hour train ride, get from train station to hotel, check-in, royal carribean cruises to ensenada drop bags), so that will leave you just over 2 days in CT. To me, I would want more time in Venice than in CT, but maybe hiking is more important to you.
If you leave early in the morning you can get to the airport for your flight. I'd personally take 1 night away from somewhere and spend the last night in Milan, as ekc has suggested. A better plan might have been to fly home from Rome, although not a great deal better. You might consider visiting 1 less location in favor of more time in the others.
I should add, those suggestions reflect my preferences to a certain extent, and very possibly not yours. As any suggestions here will. A forum is really a better resource for logistics than it is for how you spend your time which is so subjective. For instance, despite the great art, I'm not a fan of Florence. So my own trip would likely be Venice, Lucca OR the CT, and Rome.
At that time of year, I would usually say start in the north for weather purposes and work your way south. Departing from Milan puts a crimp in that plan. The most efficient royal carribean cruises to ensenada itinerary would probably be:
Rains don't start in November - it can rain at any time. And if you look at the map of the CT trails you will see that there are some closed currently due to bad conditions in previous years. Yes, Nov can be cooler as well - 45 and rainy really royal carribean cruises to ensenada isn't hiking weather IMHO.
And I can;t figure out exactly how much time you have. You are talking days when you should be figuring where you are spending the nights. (Two nights is one full day - not 3 - not matter what the tour groups or cruises may tell you.)
I think October weather will be temperate anywhere you decide to go, rain or no rain. You have 11 days on the ground, excluding arrival and departure days. If you go to 4 places, subtract 3 travel days, leaving 8 full days, not enough.
I'd concentrate royal carribean cruises to ensenada on Venice Rome and do a pass-through of one more location. If you start with 3 days in Venice, go directly to Rome for 3 days, you'll royal carribean cruises to ensenada have 2 left. If you stop in Florence, skip the CT.
Although you're flying into Milan, you're spending no time there, so it would make sense to fly into Venice or Rome if possible. You'd then recover royal carribean cruises to ensenada from the jet-lag without much more travelling and when leaving, you can be in the right place at the right time.
I'd agree that Cinque Terre is too far off your route to blend in time wise,(and in IMO in any case, not worth the effort to get there. All you're likely to get are muddy trails and OK villages) but the rest hinges on being able to alter the in/out airports.
As far as enjoying cooler weather in the Midwest, be aware that inland cool weather and seaside cool weather are two very different things. If you get a damp, cool day in CT, it's not going to be enjoyable.