Florence is undeniably a destination that draws you in, with its iconic domes and the promise of indulging in truly Italian living. But as I discovered, sticking solely to the city center means missing out on a wealth of incredible experiences just a short trip away. My family and I found that venturing out from Florence opened up a whole new dimension to our Italian adventure in 2026. We realized early on that Florence is a fantastic base, perfectly positioned to explore so much more of what this beautiful country has to offer.
Exploring Beyond Florence
The ease of travel from Florence is truly remarkable. High-speed trains connect you to major cities in mere hours, and even smaller towns are surprisingly accessible by regional routes or organized tours. My husband Michael and I decided to make the most of this convenience, planning a series of day trips that offered diverse tastes of Italy. For the kids, Lily and Ethan, each new destination felt like a fresh discovery, a chance to see different landscapes and experience new things.
Classic Seaside Beauty
Cinque Terre Wonders
One of the absolute highlights for us was Cinque Terre. This iconic stretch of five ancient seaside villages clinging to the Ligurian coastline is every bit as stunning as the photographs suggest. We took a train from Florence, and the journey itself, while a few hours, was filled with anticipation. Arriving in Riomaggiore, the southernmost village, felt like stepping into a postcard with its colorful houses tumbling down to the harbor.
We spent the day hopping between the towns of Riomaggiore, Manarola, Vernazza, and Monterosso. Each village has a unique charm, from the cliffside vineyards of Manarola to the picturesque harbor of Vernazza. Lily, our seven-year-old, was fascinated by the colorful buildings, constantly pointing them out and asking to take pictures. Ethan, at four, was mostly thrilled by the boat rides between some of the villages.
We enjoyed fresh seafood right by the water and took leisurely strolls along the coastal paths, though some sections were more challenging than we anticipated with the younger kids. If you have more time, spending a night or two here is highly recommended, but as a day trip, it’s certainly achievable and incredibly rewarding.
Tuscan Wine Adventures
Chianti’s Rolling Hills
No trip to Florence would be complete without exploring the famous Chianti wine region. Michael, a big wine enthusiast, was particularly excited about this day trip. We opted for a guided tour that picked us up from Florence, which was ideal as navigating the smaller roads and vineyards by ourselves wouldn’t have been practical, especially with the children along.
The tour took us through breathtaking landscapes of rolling hills dotted with cypress trees and vineyards. We visited a couple of different wineries, learning about Sangiovese grapes and the history of Chianti wines. Even for the kids, it was an enjoyable experience. They loved the open spaces, learned to identify different grapes (or tried to!), and enjoyed the picnic lunches we had at some of the estates. Tasting the local olive oil and cheeses was another treat.
This trip was a relaxed affair, allowing us to soak in the quintessential Tuscan scenery. It’s a perfect way to experience the flavors and beauty of the region without the stress of driving or complex public transport.
Medieval Hilltop Towns
The Iconic Leaning Tower
Is Pisa worth a day trip
A classic Italian experience you can’t miss is a visit to Pisa. It’s incredibly easy to reach by train from Florence, making it a very convenient day trip. As soon as we arrived, we headed straight for the Piazza dei Miracoli, home to the famous Leaning Tower. Lily was absolutely delighted to take the classic photo pretending to hold up the tower, a moment she’d seen in books.
Beyond the tower, the complex of white marble buildings, including the Duomo and the Baptistery, is stunning. We took our time wandering around, enjoying the grandeur of the architecture. While Pisa is known for its tower, it also offers pleasant streets for a stroll and some lovely spots to enjoy a gelato or a light lunch. It’s a good option for families because it’s compact and offers a clear, iconic landmark that kids can get excited about.
Timeless San Gimignano
What is San Gimignano known for
For a true step back in time, San Gimignano is a must-visit. This medieval hill town, famous for its distinctive skyline of ancient spires, feels like something out of a fairytale. We took a train to Poggibonsi and then a bus, which was a straightforward journey. The town is small and wonderfully walkable, making it ideal for exploring with children.
Wandering through the narrow streets, with the towers looming overhead, was a memorable experience. We visited the Piazza della Cisterna, a beautiful triangular square, and enjoyed some delicious local gelato. The history of San Gimignano is palpable, and its UNESCO World Heritage status is well-deserved. It’s a place that sparks the imagination, and even the kids were fascinated by the idea of medieval knights and castles.
Volterra’s Dark Charm
What to do in Volterra
Volterra offers a slightly different medieval atmosphere. With its orangey-brown buildings and a more solemn vibe, it has a unique historical depth. We learned about its Etruscan and Roman past, which was fascinating. The ancient city walls still stand, and within them, you can find remnants of Roman baths and a theater complex.
Exploring the Roman Theater was a highlight, imagining performances from centuries ago. The Palazzo dei Priori is also impressive with its medieval frescoes. While perhaps less immediately appealing to younger children than San Gimignano’s distinct spires, Volterra provides a rich historical context that Michael and I thoroughly enjoyed. It’s a less crowded option that offers a deep dive into Italy’s ancient history.
Lucca’s Walled City
Can you walk around Lucca
Lucca is a gem. Known for its intact Renaissance walls, the entire city center is encircled by these impressive ramparts. We took a bus from Florence, which was a pleasant journey through the Tuscan countryside and arrived in under two hours. We spent a good portion of our day cycling around the top of the walls, which is a fantastic way to see the city and very accessible for all ages.
The streets within Lucca are charming, with cobblestones and beautiful architecture. It feels a bit larger than some of the smaller hill towns, offering a good mix of sightseeing and city life. We enjoyed browsing the shops and discovering hidden piazzas. Lily loved the freedom of being on the wide, tree-lined walls, and it felt like a safe and fun environment for the family to explore.
A Touch of Rustic Italy
Montepulciano’s Vineyards
Montepulciano, perched high in the Tuscan hills, offers a more rural and authentic experience. Famous for its vino nobile wine, it’s surrounded by vineyards and offers stunning panoramic views. We decided to rent a car for this trip, which allowed us more flexibility to explore the winding roads and stop at scenic viewpoints. It also made it easier to carry back any local produce we decided to purchase.
The town itself has a medieval heart, with beautiful architecture and a sense of tranquility. The Sanctuary of the Madonna di San Biagio, located just outside the town, is a striking Renaissance church that adds to the visual appeal. For us, it was a lovely chance to experience a slightly less touristy side of Tuscany, enjoying the slower pace and the beautiful landscapes.
Monteriggioni’s Medieval Walls
Monteriggioni is a perfectly preserved medieval walled town that feels like it’s straight out of a history book. Its imposing walls and dramatic watchtowers are incredibly well-maintained. We reached it by bus, a journey of about two hours. The atmosphere here is thick with history, and walking along the battlements offers incredible views over the surrounding Chianti region.
We visited the small museum dedicated to ancient weaponry, which was a hit with the kids, who imagined themselves as knights defending the castle. It’s a compact town, making it easy to explore entirely within a few hours, leaving plenty of time to simply soak in the unique ambiance. It’s a place that truly captures the imagination.
City Escapes from Florence
Fashionable Milan
For a change of pace, we ventured to Milan. This was a longer day trip by train, but the high-speed rail made it incredibly efficient, taking less than two hours. Milan is, of course, renowned as Italy’s fashion capital, but it offers so much more. The Duomo di Milano is an absolute architectural marvel, and we spent a long time marveling at its intricate facade.
The Galleria Vittorio Emanuele II, a stunning glass-covered arcade, is a sight to behold, even if high-end shopping isn’t your primary focus. While the sheer scale of Milan means you can’t see everything in a day, we managed to get a good feel for the city’s stylish atmosphere and impressive landmarks. It was a hit with Lily, who enjoyed seeing all the fashionable displays in shop windows.
Romantic Verona
Verona, the city of Romeo and Juliet, is as romantic as its reputation suggests. The train journey was around two hours, and the city is surprisingly manageable for a day trip. Of course, a visit to Juliet’s House, with its famous balcony, is practically obligatory. It’s a whimsical experience, and the stories woven around this place are captivating.
Beyond the literary connections, the Verona Arena, a remarkably well-preserved Roman amphitheater, is an absolute must-see. We also enjoyed exploring the charming streets and squares. Verona has a gentler pace than some of the larger cities, making it a thoroughly enjoyable destination for a family day out, with plenty of history and charming corners to discover.
Bologna’s Culinary Delights
Where to eat in Bologna
Bologna is a food lover’s paradise, and we heard it nicknamed ‘Fat City’ for good reason! It’s incredibly close to Florence, with trains taking only about 40 minutes, making it perfect for a shorter day trip or even an evening excursion. It seemed a shame to miss out on its legendary cuisine, so we dedicated a good part of our day to exploring its food scene.
We indulged in fresh pasta, tortellini, and rich ragu. The city itself has a beautiful historic center with porticoes that offer shelter and character. Taking a food tour was a fantastic way to discover local specialties and understand the culinary traditions. For those who appreciate good food, Bologna is an unmissable stop, offering a delicious and authentic taste of Italian gastronomy.
Venice on the Water
A trip to Venice from Florence is ambitious but absolutely possible and incredibly rewarding. The high-speed train journey takes around two hours, making it a feasible day trip. Arriving in Venice is always a breathtaking experience, seeing the canals and the unique architecture unfold before you. We spent our day getting lost in the labyrinthine streets, taking a classic gondola ride (a splurge, but worth it for the experience), and marveling at St. Mark’s Square.
Navigating Venice with young children requires some planning, but the magic of the city is undeniable. Watching the boats glide along the canals and the sheer uniqueness of a city built on water captivated Lily and Ethan. It’s a place that feels otherworldly, and even a single day allows you to capture its enchanting essence.
Rome’s Grandeur
What to see in Rome in a day
The longest day trip we undertook was to Rome, but thanks to the high-speed train service, it’s entirely doable in a single day, taking just about 1.5 hours to reach the city center. Rome is, of course, immense, and a day is hardly enough to scratch the surface, but we focused on hitting the absolute highlights. We made sure to book tickets in advance for the Colosseum and the Roman Forum, which helped us save precious time.
Seeing the sheer scale of the Colosseum and imagining the gladiatorial contests was awe-inspiring. We also managed to toss a coin into the Trevi Fountain, a quintessential Roman experience. While it was a whirlwind, seeing these iconic landmarks in person was an unforgettable experience. It’s a trip that requires stamina but offers an unparalleled glimpse into ancient history.
Lesser-Known Gems
Arezzo’s Artistic Charm
Arezzo proved to be a delightful surprise. It’s easily accessible by train in just 30 minutes, making it a perfect, shorter day trip. The town is known for its gold craftsmanship and has a rich artistic heritage. We visited during a monthly antique market, which was a treasure trove of unique finds and local crafts.
The medieval architecture is beautiful, and the main piazza is particularly striking. Arezzo offers a more relaxed vibe than some of the larger cities, and it’s a great place to explore independently, soak in the local atmosphere, and perhaps find some unique souvenirs. It’s a reminder that sometimes the smaller destinations offer just as much charm and character.
Livorno’s Coastal Breeze
As a contrast to the inland Tuscan towns, Livorno offered a welcome coastal experience. This humble port city is known for its seafood and maritime culture. The train ride from Florence took about 1.5 hours. Walking along the Terrazza Mascagni promenade with its striking black and white checkerboard flooring and ocean views was a refreshing change of scenery.
We enjoyed sampling the fresh local seafood, a perfect end to a day by the sea. It provided a different perspective on Italian coastal life, away from the more tourist-heavy beach resorts. For a taste of a working port city and a breath of fresh ocean air, Livorno is a great option.
Cortona’s Picturesque Views
Cortona, famed as a filming location for “Under the Tuscan Sun,” is as pretty as you might imagine. It’s an easily accessible hill town, reachable by car or public transport in about 1.5 hours. The town is compact and easily explored on foot, making it ideal for families. We enjoyed its museums, including the Etruscan Academy Museum, and its archaeological park offered a glimpse into its ancient past.
The views from Cortona over the surrounding valley are simply stunning. It’s a town that invites you to wander, discover its charming streets, and enjoy the peaceful atmosphere. With its museums and beautiful setting, it’s a well-rounded destination for a day trip, offering culture and scenic beauty in equal measure.
Planning Your Day Trips
Is it worth making day trips from Florence
Absolutely. Florence is ideally situated to be a launchpad for exploring so many facets of Italy. The efficiency of the public transport system, particularly the high-speed trains, makes it remarkably easy to visit a wide array of destinations, from major historical cities to charming medieval villages. Each day trip we took offered a unique perspective and enriched our overall travel experience.
Can you do day trips to Tuscany
Without a doubt. Tuscany is practically on Florence’s doorstep, and there are numerous ways to explore the region. Whether you prefer organized tours, regional trains, or buses, getting out into the Tuscan countryside for wine tasting, sightseeing in hill towns, or simply enjoying the landscapes is straightforward and highly recommended.
For us, these day trips were not just add-ons; they were integral to experiencing the diversity and richness of Italy. From the colorful villages of Cinque Terre to the historical grandeur of Rome, and the culinary delights of Bologna, each journey offered something special. Making the most of Florence’s strategic location truly expanded our Italian adventure for the better, and I’d encourage anyone visiting to embrace the opportunities right outside the city walls.