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Northern Italy itinerary advice & airport/driving/train questions

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For a potential solo 2 week trip to the north of Italy this month or next, I would like to visit Florence, the Tuscan countryside, Cinque Terre, and Veneto to see Verona & Padua. Possibly add in Ravenna and Milan if time permits. Any suggestions on stops to include or not in this area would be greatly appreciated! I've already seen Rome, Venice, Capri, and Naples. Any comments on feasibility of finding rooms last minute in August?

Airports and driving vs. train questions:
Would flying into Florence and out of Milan be a good idea (or vice versa), or just stick with Rome? Any thoughts on renting a car vs train travel on my own? I drove in southern France but found it stressful at times. Can any one compare driving in northern Italy vs south of France? It seems the places above I want to go to are almost all connected by train except perhaps Ravenna. I like the flexibility a car affords and being able to time things to avoid the tour bus crowds, but not sure I want the stress of driving again.

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    You've mentioned 5 (or possibly 7) places. You have (apparently) 14 days. "Tuscany countryside" is vague, but I'd say you probably need to pare down your list.

    You either decide where you're going to go and pick appropriate airports and flights, or find the flights/fares/airports that work best for you and figure out what you can realistically see between arrival and departure.

    Cars are best for exploring the countryside and very small towns, and trains are better if you're only moving from one city to another city to another. Many/most towns in Italy have a limited traffic zone (Zona Traffico Limitato) that you can't drive into except under very limited circumstances. If you decide to drive, you'll need an International Driver's Permit.

    If you're seriously thinking of going this month or next, you should investigate lodging availability in your budget range in these destinations.

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    Ravenna is also accessible by train, so I wouldn't advise renting a car, unless you'll be staying in the Tuscan countryside for several days; in that case, I'd get a car just for that part of the trip. If you mean to stay in Florence itself, there are some very nice countryside tours, featuring wine and local cuisine. Since you have limited time, this might be your best option.

    I live in Italy, and have never driven in France, so I can't really compare the two situations. However, going to the places you're going, I would prefer the train, even as an Italian resident with her own car. Parking in cities is difficult and expensive, tolls are high, and fuel is expensive. On the other hand, trains are fast and relatively inexpensive, and it's just a matter of convenience to use the train where possible.

    Flying out of Milan makes sense if you'll be in the Veneto. As for flying in, I would consider Florence, Pisa, and Rome. You don't say where you're flying from, but I would pick one of these three based on price and convenience.

    Florence airport would certainly be the most convenient, except that you usually have to make a connection in Rome, unless you're coming from another European country. The flight from Rome to Florence takes a little less than an hour, and the connection time would probably be at least 40 minutes; it could take considerably longer, because flights to Florence are not very frequent. Then it would take about 20 minutes to get from the airport to central Florence. Also, flights to Florence tend to be more expensive than flights into Rome. All in all, it might be quicker and cheaper to take a flight to Rome and proceed to Florence by train. However, you should compare these options, considering the time and cost of onward travel.

    Rome is connected to Florence by fast train, and you could go directly there from the airport. There are two direct trains each day, at 11:08 and (I think) 15:08, but you can also take much more frequent trains that connect to Florence in Rome. From central Rome there are trains to Florence nearly every half hour at busy times of the day.

    If you fly into Rome, unless you take the direct train, you would get an FL1 train from the airport to Rome Tiburtina station, where you can get the high-speed train to Florence. You can buy your tickets at the travel agent at the airport train station, who sells train tickets to all Italian destinations, without commission; there's a ticket window at the station, but they only sell tickets into Rome. All told, it takes about 2 1/2 hours from the airport, but part of that involves making the connection in Rome. 1 1/2 hours will be on the comfortable high-speed Frecciarossa train, which has bar service. The total cost will be €52 for tickets bought on the day of travel, or €54 if you get the direct train.

    There are discounted tickets for the Frecciarossa if you buy online well in advance, but I don't advise that, because it's impossible to know which train you can catch, and the tickets are good only for the one train you choose.

    As for your itinerary, I would honestly reconsider the Cinque Terre. At this time of year, it will be absolutely sinking under the weight of the tourists, and not a pleasant trip at all. It takes a long time to get there and to get away, from any of your other destinations. You can't park in any of the towns, and the trains are so overcrowded that often the tourists can't even find a place to stand on the station platforms. If you want a waterside location, I would suggest the Lago di Garda, which is also more convenient from the Veneto area. There will also be a lot of tourists there, but they'll be much more spread out over a larger territory, instead of packed in like sardines in five tiny villages.

    Ravenna is about two hours by train from Padova, with a change of train in Ferrara, so you could even make a day trip from Padova, or you could spend two nights in Ferrara, which is a charming town with a beautiful ducal palace.

    I can suggest an itinerary which comprises four nights in Florence, with a day tour to the Tuscan countryside, followed by three nights in Padova with a day trip to Ravenna (or two nights in Padova and two in Ferrara). Then you could go to Lake Garda for three nights, followed by two nights in Verona and a final night in Milan to be convenient to the airport for the flight home. If your flight isn't in the morning, you could leave from Verona.If that leaves you any extra nights, I would probably an extra night to Lake Garda; or, if you're very interested in Italian Renaissance art, add it to Florence. If you decide to skip Ravenna, spread the extra time around as you please.

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    I meant to add that there are some direct flight from overseas locations to Pisa, especially in the summer. From Pisa airport,
    there's an airport bus (Terravision) to central Florence that costs €4.99, departs frequently, and takes one hour. Again consider the difference in the cost of the flight. I wouldn't consider Pisa if it would require a connection somewhere else.

    Also, there may be options for flights into Florence connecting in some other European city rather than Rome.

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