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10 days in Tuscany Italy: Travel Guide

Tuscany Italy Views

This past summer we spent 10 days traveling to Italy. While there were may hiccups on this trip from last minute lodging cancellations and changes, cancelled flights, speeding tickets, lost luggage, flat tire on the rental car, train changes and cancellations, and long days of travel, this trip was still a dream trip and we got to see and do so much in a short time. Of course this is barely scratching the surface of everything that Tuscany and each of the larger cities offers so if you have more time, you could easily build in additional days for deeper exploration of the big cities especially Florence and Rome. Keep reading for everything we saw and did on our 10 day trip along with where we stayed.


Please note these details only outline at a very high level the things we did each day. If you're interested in more on each city- let me know!


Where we stayed:

Before we even left for our trip we had lodging issues. Two days prior to leaving the beautiful villa that we had booked on airbnb had a gas leak and they had to cancel our stay there. This was unfortunate given how excited we all were to stay here and the closer proximity to everything we had planned. But the owner of the property and Airbnb helped us find another wonderful villa that had everything we needed and more. The hosts were wonderful, the scenery was gorgeous, and the stay was great however it was just a bit further from all of our planned stops. It was nestled right up in the hills of Tuscany.

Tuscan Villa

Villa Gelsi was welcoming and so helpful with books of local recommendations, a host who offered daily fresh bread service (bread brought to you by them). Such a quaint and authentic place to stay if you really want to experience authentic small town Tuscany!



Day 1:

Travel day- We left Chicago O'Hare airport in the afternoon- about 4pm CST. This was strictly a day of travel. Our flight was about 8 hours and we did have a layover in Frankfurt as well.

Woman on a plane holding champagne

Day 2:

Travel day part 2. We landed very early in the morning in Frankfurt local time was about 7am. We were rushed through back tunnels of the airport and processed through a backdoor immigrations station in order to make our tight layover (only 1 hour time) only for our flight to be cancelled. We were supposed to fly to Florence and were kindly rebooked on a much later 9pm evening flight. We unfortunately or fortunately (which ever way you look at it) got to spend the day in Frankfurt. We left the airport and took the train into the city to have a bier and Schnitzel and get some fresh air.

Woman standing in front of train tracks

We also spent quite a bit of time coming back through security and even more time enjoying the airport. Ugh. We finally got to Florence and got our rental cars about 11pm local time and then had to drive just over 1.5 hours to our Villa. This was the longest travel day(s) of my life to date.


Had we not had the disruptions we did have plans to explore local towns like Volterra.


Day 3:

This was planned to be an "open day" to hang at the pool at the villa, catch up on sleep (thanks jet lag) explore other small villages and towns , or do as we pleased in the moment.


Due to all the travel chaos, this was actually the day we slept in a bit, went to the local grocery store to have an authentic breakfast on the terrace and went to Volterra. By the end of the day we were all very tired and decided to have a homemade dinner and just relax back at our Villa. We had some wine and snacks we bought in Volterra along with what our villa host left us in our welcome basket- pasta and local sauce along with fresh basil. It was a treat to be able to cook and just enjoy each others company after a long 2 travel days!

Family eating a meal in the hills of Tuscany

In Volterra heres what we did:

  • Shopped

  • Visited the Etruscan gate/the oldest arch in the world

  • Explored the city center and Piazza dei Priori

Volterra Italy

Day 4:

Today was spent in Florence. This was about a 1 hour 45 minute drive from our villa. We go up early and got on the road with enough time or so we though to make it to our first activity. Be warned if you don't have to drive in the city- DON'T. We spent so much time just coming into town and trying to park on the outskirts. We ended up parking at the main train station parking garage which was easy in and out and a great clean, safe more "American sized" garage.


We then walked into the city center and went to the Galleria Academia which is where the Statue of David is located. We had booked skip the line tickets ahead of time, which was absolutely critical. You can do the same here. We got to bypass the whole line and go right in and save at least 2-3 hours. One thing to note is that this building has security (think like the airport). David was absolutely majestic to see in real life! There isn't much else to see in the building other than a few smaller art exhibits but we aren't huge art people.

Duomo Florence/Firenze

Shortly after we had a tour of the Duomo booked. This was booked through Viator. Our tour combined the history, the baptist building, the outside of the building and the outside of the bell tower. It also had a portion where you could explore the museum with the guide and finally what we were most excited about was climbing the inside of the dome (over 400 steps up) and finally ending on the roof of the Duomo to take in spectacular views of the city. This was an absolute highlight of the trip and view that I will not forget.

We had some gelato and and Apperol Spritz on the plaza and listened to a local musician play his accordion while we came down from the high of being on top of the city.


Lastly, we walked across town and took in some sights including Ponte Vecchio on our way to one of the best tings we did this whole trip- a pasta cooking class. This Pasta Mania cooking class was also booked through Viator. The exact class we booked is here. This class was one of our families highlights of the entire trip! We had the absolute best teacher Valentina who was funny and witty and made learning how to cook fresh authentic Italian pasta so much fun. She shared her experience learning how to cook pasta with her grandmother with us and finally she finished cooking the pasta and plated it for us to enjoy. It easily is in the top 5 meals I've ever had- it was SO delicious.

Woman and man holding homemade pasta

Day 5:

Cinque Terre Vernazza Italy

Cinque Terre was our destination of day 5. This was a bit of a drive being 2 hours from our villa but again well worth it in my opinion. We got up early and drove the distance to arrive at Monterosso al Mare which is one of the villages of Cinque Terre. We parked in a garage just before getting into the city. We planned to do the hike from there to Vernazza and prior to heading to the trailhead we grabbed a quick proscuito bread at a walk up window. The city was not too busy yet but it was still early.


The trail between Monterosso and Vernazza is 3.5 km or just over 2 miles long and is marked as a moderate hike. Its also known to be the most strenuous hike when comparing all of the hikes between Cinque Terre villages. It took us just over 2 hours to complete. At the entry to the trail on both sides there is a booth where you have to pay a small fee to use the trail. We were able to pay with a credit card but when arriving on the other side in Vernazza there was another couple who was turned away for not having cash so to be safe- prepare to have cash on you!

When we arrived in Vernazza, we took a quick swim, grabbed pizza for lunch right in the main plazza and had some gelato. It felt so good to relax and enjoy the scenery of the town and feel some real iconic Italy vibes. We opted to not continue on to hike to the next village because we had a few people from our trip stay back at the villa and relax poolside so we wanted to get back to them. Instead we took the ferry, which you have to pay for at the doc (again with cash!!), back to Monterosso al Mare and drive back to the villa.


We had dinner in Bibonna, Italy that night, a small local town close to the villa we stayed that was top 2 meals I've ever had. The pasta was to die for and the environment and company at the table was wonderful. A true iconic Tuscan experience.


Day 6:

Woman sitting on a wall in the hills of Italy

We had planned to go to Sienna that day in our trip planning but it was a bit longer of a drive and we opted to go to San Gimiginao which was a bit closer. This is a medieval town known for its towers and world famous gelato. Our group all split up and did different things while here. Some had lunch, some climbed the towers, some explored the hidden tunnels and views of the city. We also all did some shopping. And of course, I had to see what this award winning gelato was all about. It was the absolute best melt in your mouth gelato I've ever had. The line looks so long but it moves along so quickly and worthy of the awards it received over the years. I recommend checking this town out and make sure you get yourself a treat at Gelateria Dondoli.


That evening we had plans to have a private winery tour and dinner nearby. Unfortunately the weather cancelled the plans to go into the vineyards but we still got to check out the winery and be served a 4 course meal with wine parings from onsite.

Family eating dinner at winery

Day 7:

Day 7 we went to Pisa. There isn't much to see and do here in my opinion and its a rather touristy city however we had to see the iconic Leaning Tower. We got tickets to climb the tower- which most people don't know is an option so hot tip definitely get the tickets- you can do this day of in the building in the plaza. We had to wait a few hours to use our tickets at the allocated time slot so while we waited we got pizza for lunch at a touristy little restaurant. For being a small quick service restaurant, it was dang good pizza.

Man and woman standing in front of Leaning Tower of Piza

And on the way home we stopped at a beach called Spiagge Bianche. This was not a touristy spot but was absolutely packed with locals. We found this beach by zooming the coastline on Google Maps and it had the absolute bluest clearest water. We took a quick dip and then headed back as we had to get some rest leading up to our biggest day of the trip.

Woman in the ocean

That evening for dinner, we had another ionic charming Italian dinner. I love getting lost in small cities and living like a local in these destinations. We found ourself at Ristorante La Pergola Pizzeria in Casale Marittimo. There were locals walking their donkeys home for the evening through the streets of town and to me it doesn't get much more quaint and local than that.


Day 8:

Day 8 was our longest day yet- we spent the day in Rome. We got up at 3:00 am to drive from our villa into Pisa where we caught the train to Florence, transferred trains, and then finally made it to Rome. Directly from the main train station we walked to our first tour meeting spot. This was a guided Segway tour through Rome. This is the exact tour that we did- https://viator.tp.st/JY75SSo7 We met our guide, had orientation, and off we went on our 3 hour tour of the city. We hit all the major highlights of the ancient city in a quick and abbreviated way.

Woman standing in front of the Colosseum
Standing in front of the Colosseum in Rome
Family riding segways

We had about 1.5 hours before our next tour which was at the Vatican City. We elected to eat at a corner restaurant where they had sandwiches inside for grab and go, quickly found out how to use public transportation in Rome, and bused over to the Vatican. Here we were instantly overwhelmed but once we were inside and going on our tour with our tour guide things started moving along. Again we had a three hour tour.


Upon completion of the Vatican Museum tour we opted to grab another quick bite to eat as we were starving. We did this at a touristy restaurant directly outside of the Vatican City walls. Rain was coming and we were all exhausted so we grabbed a quick gelato, headed back to the main train station, switched our pre-booked train tickets (NOTE- there is an emergency/short time frame ticket booth to use) for immediate needs instead of waiting in lines at the main train office) and headed back to Florence, Pisa, and back to our car where we found it with a flat tire.


Day 9:

Day 9 was a scheduled "open day" following the completion of our busiest and longest day of the trip - Thankfully it was planned this way because some of us had to deal with the car's flat tire, some of us wanted to catch up on sleep, some people opted to swim in the villa's pool, and others wanted to explore more locally. Keith and I did end up exploring more locally near the villa which included touring a VERY small local winery out of a man's home and checking out a local grocery store. I always love seeing the local side of each location too!

Woman holding a glass of wine in Italy

At the end of the evening we had a local chef come prepare us a meal at the Villa and it was a wonderful way to wrap up the trip. He used local herbs, and also had wine pairings. He taught us about how he prepares the dishes and even shared some family stories about cooking and his learnings throughout the years. I highly recommend this type of experience in a new place.


Day 10:

It was time to head home. Travel day on the return is always bitter sweet for me but it means I'm headed back to my routine, back to my kiddos, home, and reality. We had another early one- up at 2:00am local time to head back to Florence to return our rental cars, get checked in, and board our flight to Munich. We had a short layover there where we grabbed a quick bite to eat in the Lufthansa business class lounge, and then finally boarded our long haul flight over the ocean and back into Chicago O'Hare.


This was an absolutely amazing, magical, whirlwind, somewhat stressful, and complete bucket list trip! I am so grateful and thankful for this opportunity for this adventure. Already dreaming of the day I'll go back to Italy! ❤️



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Maria Elizabeth




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