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Italy Itinerary for May 2016 (Rome, Teramo, Montefortino, Florence, Lucca, Cinque Terre, Milan)

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Hello! I am planning a trip for myself, my husband (in our mid-20s) and my parents (in their mid-60s) in May. One of the big things that we are doing is visiting towns that my great grandparents on my Mom and my Dad's side lived in before immigrating to the US. So, we are trying to fit in all of the places we want to see in the time we have. I realize that we may not have the most time in some of the big tourist cities/towns, but this is the first trip to Italy for everyone except my Mom and it is important to visit the places where our ancestors lived and get a taste of a few different regions. This is our current itinerary:

Day 1: Fly into Rome and arrive mid-morning (direct overnight flight from Boston), check in, get settled & sight see
Day 2: Sight see in Rome
Day 3: In the morning sight see in Rome, in the afternoon pick up a rental car and drive to Teramo
Day 4: Teramo and Montefortino (towns my maternal great grandparents lived) possibly Ascoli Piceno on the way
Day 5: Drive to Florence, considering stoping in Siena for half a day on the way. (don't know if that is long enough in Siena or if that would be worth it)
Day 6: Florence
Day 7: A day trip to Lucca (town my paternal great grandparents lived) - Return rental car
Day 8: We say goodbye to my parents, train to Pisa for a few hours to see the tower on the way to Cinque Terre - staying in Riomaggiore
Day 9: Explore the towns of Cinque Terre
Day 10: Train to Milan in the morning & sight see in the afternoon
Day 11: Early flight out of Milan Malpensa airport to Brussels & then onto Paris for the rest of our trip

My questions are:
1. Is this itinerary reasonable, enough time in the places we are visiting?
2. Is it reasonable to stop in Siena for a few hours on the way to Florence from Montefortino? Or should we just drive straight through to Florence?
3. Should we stay in Florence, Lucca or the surrounding countryside??
4. We all LOVE wine and would love any recommendations for wine tours based out of Florence or Lucca.
5. We also LOVE food & cooking, any recommendations for cooking classes in Rome or Florence?
6. My husband and I are a little stumped about where to stay in Milan. We want to sight see in the city, but have an early flight (be at the airport by 5:30am) and know that the airport is a ways out of the city center. Any tips are appreciated.

Sorry for all the questions, but any answers, tips, recommendations would be helpful!! Thank you!

Posted by
4152 posts

1) In my opinion, no. You're not giving yourself enough time in any location to actually enjoy them or see what they have to offer.

2) No, you won't have enough time to do anything in Siena before needing to leave for Florence. Personally, I would drive straight to Florence and return the rental car. You won't need it for the rest of your trip. You can train from Florence to Lucca easily.

3) You only have a single day for Florence and a partial day for Lucca. Again, for me, that's too much travel. I don't think it's going to matter if you stay in one of the other for the single day in each.

4) You don't have time for a wine tour.

5) You don't have time for cooking classes.

6) You are there for just a few hours, you won't get to see much of the city. Pick a hotel with good connections to the airport.

Personally, I would rearrange this trip a bit.

Spend more time in the two areas where your parents are from and skip Florence and the CT. I would stay a few nights in each place so that you have time to explore and not do just a "drive by". If you have more than just a single day in each of these locations you might be able to fit in a cooking class or wine tour but you really don't have enough time for those.

Donna

Posted by
11613 posts

Your present itinerary allows no time for the slightest thing to go wrong; one misstep and the dominoes will start falling.

You have one day for both ancestral cities? I would give each a day.

Skip Cinque Terre this trip and add the time to Lucca (another ancestral city) or Firenze.

You might be able to get a food and wine tour from Firenze, pretty much an all-day affair that will take you to a couple of cities, plus lunch at a winery.

You could spend your last night in Milano and the night before departure have your hotel reserve a taxi for you at 4:30am - at that hour there will not be much traffic, you can get to MXP in an hour. Or stay at an airport hotel but some shuttles don't run that early, so a short walk or taxi. If you do spend the night in Milano, I think the Cadorna station area is closer to MXP.

Posted by
11294 posts

I don't know anything about Teramo or Montefortino, but Lucca is a lovely city. Many who don't have family connections spend a day trip there from Florence. So I agree you should spend more time there. It's also close to Pisa, and you can take a bus or train between the three cities of Lucca, Pisa, and Florence - in any order - easily. It happened in March 1989, but one of my most memorable travel days was going from Florence to Lucca in the morning, then from Lucca to Pisa after lunch, then back to Florence. By getting to Pisa later in the afternoon, the souvenir vendors were literally packing up, the worst of the crowds had gone, and the marble in the Field of Miracles (where the Leaning Tower and Duomo are) looked lovely in the afternoon light.

I'd definitely prioritize the places with family connections over places like the Cinque Terre, which may be pretty but won't be as meaningful to you and your family. I also agree that you shouldn't plan on so many "few hours" and "half day" stops. See fewer places, and enjoy them more. Italy is better when savored than when checked off a list.

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