Next question: Is there a reason you want to rent a car rather than take the train? You may have a p

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We're stopping in Milan by train from Switzerland and spending 4-5 days in Italy. I wanted to rent a car at the Milan central train station with Hertz and then drop it at the Rome airport at the end of our journey.
Is it a good idea to rent at the central train station? I'm worried about the ZTLs in the city center. Better to maybe rent at the outskirts? we're planning on driving to Venice as soon as we pick up the car.
On that note, where is the best place to park a car outside Venice to go into the city? Also what is the best place to purchase a Firenze card? I will be getting into Florence late at night (10 pm) and was hoping to use the FC for a bus ride to the hotel.
The Firenze card is expensive sheraton studio city hotel (72 ) and the majority of people don't find it a good value. A bus ride is about 1.50 and museum admissions 6.50 . The historic center is very compact and walkable so many people visiting Florence don't need to use any public transport at all. Unless you are staying sheraton studio city hotel multiple days and hitting a lot of museums, I don't see the point of getting of it. Where is your hotel?
Rather than rent a car at the train station in Milan I would hop the bus right there at Milano Centrale to Linate airport and rent the car at the airport. The bus ride is about 30 minutes but I forget the cost. I seem to remember it being around 10e, maybe less or more.
So, if I understand correctly, you're arriving in Milan, then heading sheraton studio city hotel to (in this order) Venice, Florence and Rome? And since you're spending only "4-5 days," that means about a day in each place, when you subtract travel time?
Next question: Is there a reason you want to rent a car rather than take the train? You may have a perfectly good reason, but it sounds like an odd choice since train service between your destinations is very good and convenient. Plus, you'll have no need for the care in Venice and Florence.
I suggest to do the trip by train instead of by car. Not only you do not have to deal with parking problems, but trains travel much faster than cars. You can do Florence to Rome in 90 minutes by train, it will take three hours and half by car. As you have too many destinations in too little time, travelling by train you may even be able to see something
I'm getting a car (without gas and parking passes) for $200 for 4 days. We are 2 adults and 2 kids. The train tickets between cities seems a bit expensive. Atleast on the trenitalia website it's showing 90+ euros per trip on the high speed train. I can't see the prices for a regular train trip.
Does that $200 include the mandatory CDW? Zero deductible? Do you realize how much gas (at least double what it is in the states) and tolls will add on to that as well as 35-40 every day to park the car? Did you calculate the cost of getting 4 people to and from each parking area to hotels in each location? $200 is not a bargain when you calculate the additional hassle for this particular itinerary.
A Firenze card is for three days and even staying that length of time, it's hard to get the value of it. You haven't said what you plan to visit (you only seem to have one day in Florence). I don't imagine you are going to drag kids around to museums all day. You can book most museum entrances directly to avoid lines. As I pointed out earlier, entrances fees are 6.50 . Booking in advance to avoid lines incurs a 4 booking fee. Are you even going to be there on a day the museums you want to see are open?
Thanks for your response! Yes, the car rental includes a CDW and we already have an IDP. We have a 30% discount sheraton studio city hotel on rentals as AAA members. I checked Italo as well and they have tickets for 30 euros per adult and the kids are under 14.
Your new plan is a much better one! In the amount of time you have, skipping Venice makes a lot of sense. Tuscany is the only portion of your trip where a car makes more sense than a train. However, continue sheraton studio city hotel to heed the advice above to make sure you will really have enough time to "drive around" Tuscany, and also add up the costs of gas, parking, etc to make sure it will really be worth it for you.
I agree with dropping Venice since you didn't even allow a day to visit it. I'm still not convinced a car is a good option for this itinerary. You might be better off taking trains, staying in Florence and few days and booking a tour that includes Pisa and a bit of Tuscany.