Continued from Part I: Rome and Bologna
Florence felt like a reset. After Rome’s intensity, Florence wrapped us in beauty and balance. Over three days, we explored the city at an easy pace, blending art, food, and movement. If you’re planning a trip to Italy in autumn, Florence is one of the most rewarding destinations to visit. With golden light, fewer crowds, crisp weather, and the flavors of seasonal Tuscan cuisine, fall transforms the city into something truly unforgettable. This Florence Italy fall travel guide covers everything you need to plan the perfect autumn getaway—including the unforgettable experience of truffle hunting in the Tuscan countryside.
Florence: Renaissance Art and E-Biking the City
Day 1: But First Chaos
With travel we’ve learned not all goes according to plan. The morning we were set to leave, Uber after called Uber kept canceling on us without reason. A long walk uphill to the train station, we learned that there was a marathon throughout Rome. We missed our booked train to Florence. An albeit unavoidable, but kind of costly mistake, we eventually would get passed all that and laugh about it now.
From there the pattern continued. Part of plans included a day trip out to the Tuscan country and we needed to pick up our rental car. Finding it was tricky. Not wanting to incur another giant surprise, we were overly cautious of where the ZTL zones were located. I’m pretty sure we parked obnoxiously far from our Airbnb and rolled our bags for another long walk just to make sure we’d be fine free.
Also, I had booked us an e-bike tour that afternoon. Running late from our train, not finding the car, and not knowing where to park said car made us need to head out immediately. And there were so many distractions. The amazing views from the Airbnb. A beautiful market. My inability to read and follow Google maps really set us back. We had never been late to a tour before, but there is a first for everything. We rolled in out of breath and ended up having a guide take us to our real guide.
I do like a bike tour or something similar when we go to a new city. It’s a good way to cover more ground and acquaint myself with the area. It’s also nice to have someone tell me the what I’m looking at and why it’s famous. Mostly, t’s nice to not have to read every sign in the area. Florence was busy and I’ll admit, I was slightly skeptical at first. Mixing bikes, traffic, and so many walking humans. Like the rest of the day to this point, it started off a bit chaotic. But it always ends up being one of the easiest and most fun ways to explore. (Kind of like our bike tour of Kyoto or rickshaw ride through Tokyo.)
We rode along the Arno River as the sun was setting – pure awesomeness. And as if it be more perfect, we rode through busy squares and quiet streets, and up to viewpoints that we probably would have skipped otherwise. It gave us a completely different perspective of the city. We experienced several of the neighborhoods of Florence, and stopped for snacks in a popular locals square. The excitement as we took in people watching as they started their weekends. We still saw the main sites like Cathedral of Santa Maria del Fiore (Duomo), Ponte Vecchio and Piazza della Signoria. After some time, it became less about checking off landmarks and more about experiencing it in motion. The city felt playful and accessible, especially for only have a few days – turning sightseeing into shared adventure.
Day 2: Tuscany: Truffle Hunting and Pasta Making
Of course, Tuscany isn’t just about Florence—it’s about getting out into the countryside. Our single day in the Tuscan countryside was one of the most memorable of the entire trip. One of the most unforgettable experiences we’ve ever probably ever had was truffle hunting with Luca, our local guide and his dog, Tabu. Finally, we’d take that car and suprrisingly, fear of driving quickly subsided. Rolling hills and crisp fall air set the stage for us to go truffle hunting. And it was an experience that felt so authentic and deeply connected to the land.
Watching the dog work and learning about the tradition behind truffle foraging gave us a new appreciation for the ingredient long before it reached the plate. He was so completely focused, nose to the ground—watching was fascinating and hilarious, and somehow the kids were just as into it as we were. His owner had told us later, Tabu the dog was not the best sniffer of the pack, but he definitely the happiest dog of the pack. There is something special about being in the woods, waiting to see if the dog finds something, and then celebrating together when he did. “Bravo,Tabu, bravo.” It felt so natural in a way that’s hard to replicate—simple, a little muddy, and completely memorable.
Afterward, we moved from forest to kitchen for hands-on pasta making at a family house. We worked outside, panning majestic views of the family’s olive groves grape vines. Flour-covered hands, laughter, and focus filled the air as we shaped dough into something both imperfect and delicious. While our dough was resting, Nicolo brought us a charchuterie of their ocal specialty products to try as well – a variety of sausages and cheeses and fruits. So local – they were made by all his neighbors. He also brought us samples of his family’s wines and olive oils. We even got to try some of their newest dessert liquor, an olive leaf based amaro.
Nicolo and his family (Cofferi 1242) were so warm – they were like visiting family that you hadn’t seen in years. A ‘four-hour tour’ became a whole day out, plenty of wine and engaging conversation. After wating, the boys were all playing basketball in the yard. Sitting down to eat a meal we had helped create—paired with the family’s wine and sweeping countryside views—felt like the definition of slow travel. Fresh pasta, shaved truffle, local olive oil—it was one of those meals where everything tastes better because of the people your around and just being a part of the process.
The Food Scene
Florence’s food mirrored its vibes — simple pastas that let ingredients shine, and meals that lingered long after sunset. Evenings were slow, filled with conversation and the soft glow of stone streets that have witnessed centuries of life. Florence was romantic and beautiful for all the right reasons. But would it be a trip to Florence, if the American teenage tourists didn’t get the chance to engorge themselves on the famous Florentine steak? And not once, but twice. The iconic steak—thick-cut, mostly rare, and simply seasoned—is less about embellishment and more about quality. The quantity wasn’t so bad either.
Boys will be boys and stuck with the meats. I stuck with the more autumnal and seasonal dishes… hearty pastas and stews, made of vegetables and boar. And duh, paired with a glass of Chianti Classico. It’s those kind of meals that put me in my happy place! It seems, a common theme in Florence and all Italy, that eating isn’t rushed. It’s deliberate, seasonal, and deeply tied to place and people. Choosing what’s fresh, local, and traditional, you won’t just taste the city, you’ll feel it.
Day 3: How to Spend a Rainy Day
Our final day in Florence was rainy before having to catch a train back to Bologna for our flight home. I usually always leave the last day of our trips open for any last request site seeing. Those sites we only learned about by being there, and maybe some souvenir shopping. And that is exactly what we did. We started with a walk through the city that morning and as the rain picked up we stumbled across the Da Vinci museum. We had already been through the overwhelming size of the Vatican museums on this trip, so the interactive displays and managebale size kept everyone engaged for the whole visit.
If the boys were going to enjoy and splurge in Florence for its steaks, I was going to enjoy it for their craftsman leather products! While the boys hit the street markets for t-shirts and something for Jake’s wall of travel trinkets, I found myself a new purse! I’ve spent years downsizing bags – from the onset of the diaper bag to just a phone case, I’ve reset and find myself being a bag lady again!
My boys are definitely well versed when it comes to food and don’t shy from much. They don’t love to eat the standard, weeknight vegetables but I’m pretty sure that’s more for looks. For lunch, we finally made it to All’Antico Vinaio for the TikTok famous sandwiches.
Known for its famously overstuffed schiacciata sandwiches, this tiny shop draws lines that spill into the street. Each sandwich starts with warm, crisp-on-the-outside, soft-on-the-inside best bread you’ve ever tasted, then gets layered generously with Tuscan ingredients. I went with the cult favorite ‘Paradise’ – mortadella, pistachio cream, and strachiatella. No surprises that the boys went with ‘The Italian’ – ham, mozzarella, and toppings. The combinations are bold, messy, and completely satisfying, often named with a sense of humor or local flair. Located in a tiny alley way, we grabbed our sandwiches, and found a spot along the nearby piazza, eating surrounded by the hum of the city—simple, indulgent, and unmistakably Florentine.
Back to Bologna – The Last Night
And then we headed back to the Airbnb and final returned that rental car. One last train ride, we made it back to Bologna, that evening, on time. And more importantly, in time for another dinner and one last opportunity to see the city that the boys jetlag had them sleeping through the first time.
We were able to see the Towers of Bologna. We made to the markets for desserts before dinner and a stroll through the Piazza Maggiore until we found the Whispering Walls. The endless porticoes had us looking up in awe. And to cap off amazing trip there would be no ending more classic than one last family night out for pizza.
Italy Is Perfect for Family Travel
Florence (and really Bologna and Rome, too) reminded me that traveling through Italy is rich with culture. Doing it together, and as family, made it all the more fulfilling. Food becomes the universal language. Meals are unhurried, curiosity is encouraged, and everyone has a seat at the table.
Traveling in Italy was magical. Supposedly less crowded than summer, (that’s debateable) Still plenty of warm days, but some cooler weather and seasonal food allowed us to slow down and savor the experience. We chose participation over checklists, connection over constant movement.
I still think about the quiet beneath the Colosseum, the smell of fresh pasta dough, the hum of e-bikes on cobblestone streets. Permanently engrained, I won’t be able leave the taste of truffles shaved generously over a meal we helped create. More than anything, I think about how those moments felt as a family. Present, curious, and connected. As simplistic as it sounds, you lose sight quickly in the hustle of work, activities, and routines.
This trip wasn’t just about seeing Italy. It was about experiencing it through food, history, and shared moments. That is the kind of journey that keeps calling you back.
And just in case here’s the link to the part one of this trip: Rome and Bologna
Love reading about your family adventures. Sounds like a beautiful vacation! Makes me want to go there and experience all the food and culture!!