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Itinerary--looking for suggestions for beginning, between FCO Roma and Montalcino

We have a 3-week itinerary in late June/early July that has been worked out except for the very beginning, which I'm looking for suggestions on.

We initially planned to go to the Bernese Oberland area of Switzerland to spend the week surrounding my daughter's 2nd birthday. We then found out that our extended family would be in Tuscany to celebrate an important birthday a week or so earlier. We were invited to join and decided to extend our trip. This would involve some longer travel days, but we didn't want to miss the opportunity and we didn't want to change our whole trip to Italy, since we'd prefer to spend more time exploring Italy in the spring or fall when it won't be so hot.

So, here's what we have. We'd like to take advantage of our first couple days to see something different.

Day 1 -- Fly into FCO Rome and arrive at 8:15am, then ???
Night 1 -- ???
Day 2 -- Take rental car to meet up at family's villa near Montalcino in the evening
Nights 2-7 --Stay at villa near Montalcino for 6 night, while spending days exploring surrounding area and relaxing at pool
Day 8 -- Leave Montalcino first thing in the morning and drive to return rental car at Bologna airport. Take 7 minute monorail into town, store luggage at train station, then explore until 4pm train. Fast train to Venice and check into hotel.
Night 8- 10 -- Venice 3 nights
Day 11 -- Longest travel day to avoid extra hotel change in between. Leave Venice on early 7:18am train to Milan arriving 9:45am (breakfast on train). Walk around Milan for a couple hours to break it up and let our daughter run around freely at a park and then series of trains from Milan to Wengen, where we will be staying. Possibly stop in Spiez for a bit and catch the next train if we need a break.
Nights 11-16 -- Wengen - 6 nights
Day 17 -- Train from Wengen to Basel airport to pick up rental car. Take a break at Bern to explore on the way. Drive rental car to Colmar, France an hour away and check into hotel.
Night 17-20 -- Colmar 4 nights, explore surrounding area
Day 21-- Drive to Basel airport to return car and fly home.

Our original plan for the 1st day was to take the train from FCO to termini in the morning, drop off our luggage at our hotel, and spend the day walking everywhere and exploring the city. The best way to fight jet lag is to get out and walk and then to go to bed at a reasonable, but early hour. The next day, we were planning on doing a tour of the colosseum and underground first thing in the morning, then heading back to FCO to pick up our rental car around noon and start our drive north to Montalcino. HOWEVER, we realized, from there, the metro doesn't reach the city center/Navona.. The taxis in Rome don't have carseats and we weren't planning to bring one, as we'll be using carseats provided with our rental cars. Even if we manage to get a reliable airport transfer to take us to our hotel and back (which I've read from some that theirs showed up without the carseat they requested), I'm afraid if the weather is bad the day we're there, and too hot for our daughter to be out walking all afternoon, then we won't have a reliable way to safely get around. Therefore, we decided to skip going into Rome.

We changed our car rental to the morning we arrive, instead of the following day, and are now brainstorming where to dedicate the first couple days of our trip. We know we'll be exhausted and dragging, but we'd like to take advantage of the time to see/experience something we otherwise won't. The most convenient idea we had was to drive up to Orvieto, spend the night, then see Civita di Bagnoregio before onwards to Montalcino. A more challenging, but interesting, thought we had was to drive up to Piombino, leave the car, and take the ferry to Portoferraio for the night. Ideas?

I've hiked up and down mountains with her in our ergo baby 360, and we will also be bringing a child carrier, so I'm not worried whether something is stroller friendly.

Posted by
3062 posts

After landing at FCO spend your first night in Rome.
I don’t recommend spending a few hours in Bologna because Bologna needs a minimum of two nights if not more. I took a train from Venice once and stopped in Bologna for the day before continuing to Florence and did not like it. People who love Bologna spend more than a few hours there.
There is a big old square in Bologna that isn’t nearly as nice as Rome’s Piazza del Popolo. Bologna is well known as ITs foodie capital but during the hours you’ll be in Bologna the restaurants you want to patronize will be closed. I say go to Venice after dropping off your car.
Finding a hotel in Venice is not easy unless you’re staying near the train station in the direction going north. Allow this extra time to find the place you are sleeping because you are going to need it, especially when traveling with a two-year-old.

Posted by
297 posts

I like your idea of seeing Civita di Bagnoregio and Orvieto before driving to Montalcino. While Orvieto is unique, you'll never forget walking over the bridge to Civita while taking in the landscape. We were lucky to see the donkey Palio while we were there years ago.

Padua is much more interesting to walk around than Bologna. Seems like a long day anyway, you might want to get to Venice and walk around if you can't check into your hotel.

Posted by
5 posts

Thank you for your responses!
A lot of our decisions have been based off of making it work for our daughter's schedule.

MaryPat, we had intended to spend our first night in Rome, as you suggest, but ended up with issues with how to get around. We will be traveling with our 23-month-old and would not be willing to have her ride in a car without a carseat. We won't have a carseat with us and taxis don't have them. We had assumed we would take the metro like we've done in other cities, but learned how inadequate the metro system is in Rome for our purposes. We had planned to do a lot of walking during our first day there, basically walk around for hours, and then have the option to take the subway back to our room if needed, until we realized it doesn't reach the areas of interest. The buses seem to have unreliable timetables and are sometimes full. If we get bad luck and it's a sunny 90+ degree day, we don't want to risk our baby being stuck in the heat with no safe and immediate way to get back other than the long trek. I wouldn't think twice about it if it were just my husband and me. Now, however, I'm trying to figure out the most interesting way to spend our time without such a gamble of a miserable almost-2-year-old and, therefore, miserable parents. I'll be so sad if it turns out to be a beautiful 76 degrees and we missed Rome, but idk how to build flexibility into the schedule and still have everything booked in advance. Hopefully what we plan instead will make it seem like it wasn't a loss.

As to Bologna, our daughter will nap in the car for about 2-2.5 hours. After that, she is very much ready to get out and get squirming. We originally planned to drive all the way to Venice. We thought we would stop in Bologna or nearby, slightly past halfway, to eat lunch and give her a chance to get out and move. We figured we would have to park outside the city and ride in. Rather than take the time to do that and stuff her back into her carseat, we looked into fast trains. We had to pay a large fee just to return the car in Venice, so we figured if we were going to have to park somewhere anyways, might as well return the car in Bologna and save the money. We were able to book discounted fast train tickets in business with a private compartment that she could use to stand, climb on us, be disruptive, etc. for about the cost of parking the car to return it in Venice. Now she has a couple hours to nap on the way to Bologna, we can hang out there for the afternoon, then take the fast train to Bologna and go straight to our hotel apartment in Venice. I have arrived via train to Venice before without children.

Posted by
4676 posts

We don't know where you are flying from, and it is not responsible advice to tell you to drive two hours on curvy roads upon arrival after a flight on which you are unlikely to sleep well. I would just choose somewhere within an hour of Rome airport, whatever fits into your notion of a safe driving distance. Book an early check-in, head to the beach after nap time and have a leisurely day!
Southern Tuscany has many interesting sites. I find the Tarot Garden compelling but did not make it there on my last visit. Pitiglinao is gorgeous, many Etruscan sites in this area.