Seven Days in Italy

How we spent seven full days in Italy, not counting our travel days. Total trip time door to door was 10 days.

My oldest daughter has been studying abroad in Florence since late August and we had been talking about visiting her over the Thanksgiving holiday basically since she left. We were pretty indecisive about it and though we knew we wanted to go I waited until the very last minute to put the trip together.

One week before we were supposed to depart I purchased airfare and then spent two days frantically finalizing our timeline, booking hotels and planning our tours and activities.

Our two constraints in planning were time, as I have a daughter in high school and we wanted her to miss as little school as possible, and budget. We ended up with a very tight but productive itinerary and had a wonderful time.

Here is a breakdown of our seven days in Italy:

Day 1: Travel day, flying from California to Rome.

Day 2: We arrived in Rome. I had set our hotel reservation to begin the day before we arrived so that when we made it to the hotel at 9:00 am, exhausted and overwhelmed, we could immediately access our rooms and rest.

We slept for several hours and then got up and around and set out to find some food and do some sightseeing. Our hotel was located very close to Rome’s historical center as well as the Via del Corso shopping district so we were able to step out of our hotel and quickly walk to many major sites. I pre-purchased tickets to the Pantheon with timed entrance so that was our first stop. We then had a panino and did some shopping (I left my charging cable on the plane so I was happy to see a big Apple store in walking distance) and then wandered a bit, seeing the Spanish Steps and the Trevi Fountain, which is under construction right now and not much to look at.

Day 3: I had two tours booked for this day. With limited time in Rome I felt that we had to choose between the Colosseum or the Vatican and I chose the Colosseum. We did a guided tour of the Colosseum, Roman Forum and Palatine Hill with a tour company that is a travel agent favorite in Rome and it was worth every dollar. Our tour guide was fabulous and we were able to bypass the line into the Forum.

(Note, you absolutely could fit the Vatican or Villa Borghese into the schedule we had planned for this day but we were traveling with two of our kids and I have found over the years it’s better not to schedule too many things in one day. For us, it worked better to not try and fit it all in and go at a more relaxed pace.)

We had a big break in between our first tour ending and our second tour starting, so we grabbed lunch and then went back to our hotel to rest and change.

In the evening we went on a food tour across the Tiber in the Trastevere neighborhood. This was truly a highlight of our whole trip. We visited five stops, with food and drinks at each stop and our tour guide took us into a local bar for gelato. It’s a group tour but it ended up being just our family and one other couple (the perks of visiting during the low season) and we had an incredible time wandering around in Trastavere, stopping for amazing bites of food, and seeing interesting neighborhood sights. We stopped by the building where Dante Aligheri lived and the gates were open which is apparently unusual and we were able to take a look inside the courtyard. 

Unfortunately the downside of visiting in the off season revealed itself when we were caught in a downpour on the walk back to our hotel. But it was a small price to pay for a great evening.

Day 4: We packed up and called an Uber to take us to Rome Termini where we were picking up a rental car. There were two very stressful moments in our trip: when we drove our rental car out of Rome and when we returned it to Florence. We picked up the car and set the GPS to Montepulciano, where I had scheduled a wine tasting for that afternoon. The drive out of Rome was a little scary. It’s definitely doable but you must have someone driving who is confident and pretty assertive. Once we were out of the city proper and onto the freeway system driving was very easy and kind of similar to driving in the US, except for the speed limits and frightening Italian drivers.

About 40 minutes outside of Rome the landscape started to morph into what you see on postcards from Tuscany. We drove past multiple ancient hill towns and castles that seemed close enough to reach out and touch. It took about 2 ½ hours to drive to Montepulciano and find parking. We wandered through the breathtaking town, and toured through the cellars at Cantine Contucci (made famous by Rick Steves) but in the end decided to cancel our wine tasting at De'Ricci Cantine Storiche as it was getting dark and we were cold and tired. I definitely regret this now but at the time it seemed too difficult in our jet lagged state to wine taste for 1.5 hours then drive on in the dark to Siena.

It took just under an hour to reach our hotel in Siena. Our plan was to change and then head into the historic center of Siena for dinner but we all fell asleep and missed dinner.

Day 5: After breakfast and cappuccino at our hotel we embarked on a scenic drive through Chianti. Starting at our hotel we drove along the famously scenic SR 222 to Castellina in Chianti. Two things to note here - every road in Tuscany is scenic and I was very specific about wanting to take the 222 but really we never found an UN-scenic road in the Val d’Orcia or Chianti. Also, you can pick any town in Chianti and stop. They are all beautiful, they all have good food and good wine. I picked Castellina just because it seemed like an easy place to stop on the loop I had planned out but I really would have loved to see Greve and could easily have spent 2 or 3 days wandering in the area. 

Castellina is another incredibly charming town and we had a long, wonderful lunch at a restaurant called Pizzeria Il Fondaccio where we ate pici and cacio e pepe and pizza that was fired in an over right next to where we were sitting. We drank chianti and had a limoncello digestive and espresso. 

My plan for this day included a second wine tasting along our route but I couldn’t find a winery that was open or had availability on short notice. This was an unfortunate downside to traveling in late November. So we proceeded to Castello do Brolio to see the incredible views. It was well worth the stop just for the beautiful family chapel alone, but the views were stunning and there is a wine shop with tasting just down the hill from the castle and they include a free tasting with your ticket.

That evening we finally went to see the historic center of Siena. We drove and parked in a parking garage and then walked up up up up up to the main Piazza. We also walked to the cathedral, of course nothing was open except for bars and restaurants but if you are looking for food there is plenty of it.

Day 6: Unfortunately, this day was a loss. It was a travel day, as we were driving to Florence from Siena but it ended up being a day of nothing going right. One of our kids woke up sick, we weren’t sure if it was a stomach virus or a touch of food poisoning but she was unable to travel that morning. I had tentatively planned out three possibilities for that morning: Packing up and stopping at San Gimignano, stopping at Volterra or leaving our luggage at the hotel and going back to Siena for a meal and daytime sightseeing. Instead we hung around the hotel, luckily checkout times are later in Italy than they are in the US so we didn’t have to leave until noon. We drove straight to Florence where we were supposed to return our rental car to Santa Maria Novella train station. The drive itself took an hour but what we didn’t anticipate was that the Firenze Marathon was taking place that day. So we drove into a marathon route. And then the parking garage where we were supposed to return our car wasn’t allowing cars to enter. After circling a couple of times and a frantic phone call to Europcar we noticed another person trying to get into the parking lot. He was an Italian and was able to use the call button to explain to the parking attendants, in Italian, that we all needed to return cars (there was a line at this point). Finally we were allowed in and after almost turning the wrong way and driving right back out we were able to drop off the car.

However, my plan had been to taxi from SMN to the rental apartment that I had reserved and due to the marathon we could not get a taxi. So we walked. Over a mile, through marathon crowds, pulling suitcases over cobblestones, with a teenager who had food poisoning. It was a nightmare hour. You can’t believe the incredible beauty of Firenze, the dome rose up above us and I could not spare the emotion to take it in.

We eventually made it to the flat and were let in by the host and we collapsed in relief. 

Day 7: We went to a laundromat this morning to wash and dry the clothes that were rained on in Rome. After that, it was all sightseeing. We wandered, we shopped, we ate panino and pasta, we went up up up up up to the Piazzale Michelangelo to see the sun setting over the incredible landscape. We considered hopping the train to Pisa on this day but there were train strikes happening and we wanted as much time as possible with our daughter in Florence so we skipped it.

Day 8: More sightseeing. We had tickets to climb Brunelleschi’s Dome at 8:15 am. We were in the first group that went through and I can’t recommend this enough if you are able to climb over 400 stairs. It was something I will never forget. We visited the oldest pharmacy in the world, ate arancini and pizza topped with potato chips and french fries. That evening we went to the Uffizi Gallery and had a late dinner at an incredible restaurant called La Giostra.

Day 9: The second time we really got rained on which was kind of a miracle considering that we were there in late November. We had to check out of our flat and move our luggage (next time it’s backpack only in Europe). Then we did a little shopping and went to the Galleria dell'Accademia to see Michelangelo’s David. This was the only activity that I did not book in advance. It was only a short wait in line (thank you again late November) and well worth it to go through and see some of the incredible exhibits.

We headed back to Rome that evening on the train. Our tickets were for Termini station but for an unexplained reason the train stopped at Tiburtina station and we all had to get off.  Our daughter who lives in Florence had traveled back to Rome with us and she is super familiar with public transportation in Italy, otherwise I think we probably would have had a little panic. We got on the metro right there at Tiburtina and it took us almost to the door of our hotel. We had  multiple people tell us Uber isn’t usable in Rome, but we did not find that to be true. If all else failed we would have been able to Uber to our hotel. However, I was happy to check out the metro, it was surprisingly easy and user friendly, maybe even more so than the London Underground.

We spent one more night in Rome and then headed to the airport the next morning.

Day 10: All travel, Rome to California. 

Italy is a big country with so many distinct regions that you could spend a month there and not see everything. If you are fitting your trip into a window of time, it’s important to narrow down what regions or cities you really want to see and then focus in on these. My only regret from this trip is that we didn’t have more time. We could easily have spent 5 days in Rome, 5 days wandering in Tuscany and a week or more in Florence with multiple day trips. Two weeks minimum and I still feel like we would have just scratched the surface.

View our complete itinerary here: https://travefy.com/trip/6yw9rqyfka8sqz2aykcewwey7g9d6bq

If you are interested in the hotels we stayed at or planning your own trip to Italy, shoot over an email to hello@travelwesterly.com or fill out our trip planning questionnaire here.