My husband and I are planning to travel in October. Tentative itinerary is flying into Milan and renting a car. To CT for 2 nights (Monterossa), touring hill towns and staying in a town for 2 nights, then Florence for 2 nights (dropping off car), train to Venice for 3 nights, and train to Milan for 1 night before flying back to US. Need advice as to best place to stay in hill town area and if we are in Milan for only one night before leaving, should we stay near train station or near airport? (Our flight leaves Milan at 2:00 PM). Any advice is appreciated.
You don't need to rent a car to go to the Cinque Terre. You won't need a car at all at the Cinque Terre and parking is scarce.
You could take a train from Milan to Monterosso. From Milano Centrale station there are trains to Monterosso with no change required.
You don't specify which Milan airport you will be flying to. Malpensa is connected to the Central station via bus or train. The other two airports by bus only.
If you want to visit Tuscany with a car between your Monterosso stay and Florence, you can rent a car in La Spezia, near the Cinque Terre, for 3 days, then you return it in Florence upon arrival.
However some towns may not even require you to have a car. For example the bigger ones (like Siena or Lucca) don't require you to have a car.
Your flight leaves from Milan at 2pm. Are you flying to another European airport first? If so you need to be at the airport at least 1 hr prior to departure (90 min is safer). If you fly directly to outside of Europe (like North America or Australia), then you should be at the airport at least 2 hrs prior to departure.
You have not specified which airport you will be flying from to return home, but since it's not an early morning flight I see no reason for staying at a hotel at the airport. You can stay in the city your last night. If you fly out of Malpensa (which is 30 miles from the city), I would stay not too far from the Cadorna station, near the Castello Sforzesco. The Malpensa Express can take you to the airport in 35 min. A taxi takes longer and it costs a fortune (over 100 euro). If you depart from Linate airport, then you will probably take a taxi, since it's only 5 miles from the city center, so it doesn't really matter where you stay.
Edison,
How many nights will you be in Italy? It seems like you only have 10 nights, right?
Keep in mind that staying 2 nights in any one place actually only gives you one full day of sightseeing.
I'd suggest going straight to Venice once you arrive in Milan via freccia(high-speed) train.
So your itinerary would look something like this;
Arriving in Milan > Venice( 3N) > Florence(3N) > Cinque Terre (3N) > Milan (1N).
You don't need a car when in the Cinque Terre as it's very easy to visit the villages in CT via train.
In Milan, you can stay in a hotel near the train station( Milano Centrale) or near the historic center (near Milano Nord Cadorna train station).
The 'Malpensa Express' (train that you'll need to take to the airport) takes about 52 mins from
Milano Centrale (Milan's Central Station) and only 29 minutes from Milano N. Cadorna station.