Florence Is Stunning—But These 21 Day Trips Keep Me Coming Back
Florence is the kind of place that lives up to every expectation. The art, the architecture, the food—it’s all as beautiful and indulgent as you imagined. You could easily spend days wandering its streets, getting lost between Renaissance masterpieces and long, wine-soaked dinners.
But here’s the thing no one tells you at first: as incredible as Florence is, some of the most unforgettable moments happen outside the city.
Step just beyond its borders and everything shifts. The crowds thin out, the pace slows down, and suddenly you’re driving through rolling vineyards, stumbling upon hilltop towns that haven’t changed in centuries, or soaking in thermal springs tucked deep in the countryside. It’s quieter, more authentic—and somehow even more magical.
After multiple trips to Tuscany, I realized that Florence wasn’t the highlight I kept coming back for. It was everything around it.
From iconic stops you’ve seen all over Instagram to hidden gems most travelers miss, these 21 day trips are the real reason I keep returning to Florence again and again.
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21 Best Day Trips from Florence Italy
1. San Gimignano: The Medieval Manhattan
Distance from Florence: 55 km
Time: 1 hour by car; 1 hour 40 min by bus
Just a short drive from Florence, San Gimignano is like stepping into a time capsule. Known as the “Medieval Manhattan” because of its tall, tower-like buildings that once represented the wealth and power of noble families, this town is a photographer’s dream. I loved wandering the cobbled streets, getting lost in the history, and of course, stopping for a glass of Vernaccia, a crisp white wine that’s produced right here. As you stroll through its cobblestone streets, you’ll be transported to an era of knights and merchants. When you get to the top of Torre Grossa, you will be treated to the sweeping views of the stunning Tuscany countryside —don’t miss climbing the Torre Grossa! San Gimignano is close to Florence and you can visit it independently by car or bus. But, if you prefer tours, you might enjoy this one.
Pro tip: The town can get crowded, especially during peak tourist season. To avoid the crowds, arrive early in the morning or later in the afternoon. And don’t miss a stop at Dondoli Gelateria—it’s home to some of the best gelato I’ve ever had! Try the saffron or the wild berry flavors for an unforgettable treat.
Read more about the top things to do in San Gimignano!
2. Chianti Region: A Wine Lover’s Paradise
Distance: 30 km
Time: 40 min by car; 1 h 10 min by bus
If you’ve come to Tuscany for the wine, the Chianti region should be your next stop. I’ve had the pleasure of road-tripping through the vineyards and rolling hills, and let me tell you, it’s everything you imagine and more. I made sure to stop at a few wineries to taste the world-famous Chianti Classico wine, and I was blown away by the flavors (and the landscapes!). The quaint villages like Greve in Chianti and Panzano offer some fantastic food and wine pairings, too. Whether you’re sipping wine or just enjoying the view, this is one of the best ways to immerse yourself in Tuscany’s culture. You can tour Chianti wineries on this day tour from Florence, or rent a car in Florence and tour the Chianti region like a boss!
Pro tip: Stop at one of the many vineyards along the way for a wine tasting. Most offer tours where you can learn about the history of Chianti Classico and sample some of the best wines in the world. I recommend Castello di Verrazzano for an unforgettable experience. Read a related read about the perfect 3 day Tuscany itinerary.
3. Certaldo Alto: A Hidden Gem
Distance: 42 km
Time: 50 min by car; 1 hour by train
For those seeking a quieter, less touristy experience, Certaldo Alto is a real hidden gem. This small medieval town is perched high on a hill and offers panoramic views of the surrounding countryside. It’s the birthplace of the writer Giovanni Boccaccio, so there’s a fascinating literary history here, too. Take a leisurely stroll through its narrow streets, enjoy some local gelato, and sit in a small square to truly appreciate the serene vibe of this underrated Tuscan treasure. Certaldo Alto is one of the best day trips from Florence by train.
Pro tip: Take the funicular from the lower town to the top for some incredible views, and grab a traditional panino with truffle and pecorino—simple, but perfect.
4. Siena: A Glimpse into Tuscany’s Heart
Distance from Florence: 72 km
Time: 1 h by car; 2h min by train; 1 h 30 min by bus
Siena is one of those cities that truly feels like Tuscany’s heart and soul. With its beautiful piazzas, like the famous Piazza del Campo, and the magnificent Siena Cathedral, this city is steeped in history and tradition. If you can, visit Siena on July 2 and August 16 when the Palio, the famous horse race, takes place. Even if you’re not there for the race, Siena’s medieval charm and breathtaking architecture make it a place worth getting lost in for a day.
Siena alone deserves one full day. However, if you lack time, you can choose this quick-day tour of Siena from Florence or join this Siena, San Gimignano adn Montereggioni tour.
Pro Tip: Siena’s streets can be a maze, but don’t let that scare you. Getting lost here is part of the charm! Be sure to visit the Cathedral (Duomo di Siena) and the Piccolomini Library inside—it’s one of the most stunning spaces I’ve ever seen. Read more: A Perfect Florence to Siena Day Trip and the Best Things to Do in Siena.
5. Pisa: Beyond the Leaning Tower
Distance: 85 km
Time: 1 hour by car; 1 hour 10 min by train
Sure, we’ve all seen the photos of people holding up the Leaning Tower of Pisa, but the city itself has so much more to offer than just its iconic structure. I took a walk around the Piazza dei Miracoli, where the tower stands, and explored the nearby Pisa Cathedral and Baptistery. Beyond the tourist crowds, Pisa has a lovely atmosphere, with charming cafes and lively piazzas. I also recommend walking along the Arno River for a bit of peace and quiet away from the hustle and bustle. If not traveling to Tuscany by car, you can visit Pisa and its Leaning Tower on this tour from Florence or take a train from Florence to Pisa.
Pro Tip: Skip the line for the Leaning Tower by booking your tickets in advance online. Also, the Arno River at sunset offers one of the most beautiful views in the city—make sure to walk down to the riverbanks and enjoy the reflection of the buildings on the water.
6. Casciana Terme: A Relaxing Thermal Escape
Distance: 75 km
Time: 1 hour by car
Sometimes, you need a little break from sightseeing and just want to relax, and Casciana Terme is the perfect place for that. This small spa town is known for its healing thermal waters, and after all the sightseeing in Tuscany I’d done, a day here was exactly what I needed. I visited the local thermal baths and treated myself to a relaxing spa treatment. It’s a great place to unwind and recharge before continuing your Tuscany adventures. Half-day ticket (morning or afternoon) for adults is €15, and daily ticket for adults is €20. Rent a car in Florence and relax in Casciana Terme on a day trip from Florence.
Pro Tip: The best time to visit Casciana Terme is in the off-season when the thermal spas are quieter. Don’t miss out on a mud therapy treatment—it’s incredibly rejuvenating!
7. Cinque Terre: Colorful Coastal Beauty
Distance: 190 km
Time: 2 h 30 min by car; 2 h 15 min by train
A little further from Florence, but well worth the day trip, is the stunning Cinque Terre. Five colorful villages perched along the Ligurian coastline, Cinque Terre is a UNESCO World Heritage site that offers breathtaking views, dramatic cliffs, and sparkling blue waters. I spent the day hiking between the villages, soaking up the beauty of the rugged coast and the vibrant buildings. Whether you’re into hiking, eating fresh seafood, or simply strolling along the cobbled streets, Cinque Terre will steal your heart. You can visit Cinque Terre with an optional hike on this day tour from Florence.
Pro Tip: Cinque Terre’s trails can get crowded during the high season, so consider taking the train to travel between villages instead of hiking if you are traveling independently. Also, wear comfortable shoes if you hike—it’s more challenging than it looks! I hiked Cinque Terre in May when the nature was blooming. Read more about my Cinque Terre hike.
8. Lucca: A Charming Town with a Twist
Distance: 80 km
Time: 1 hour by car; 1 hour by train
Lucca is often overshadowed by its more famous Tuscan neighbors, but this town has its own unique charm. Known for its intact Renaissance-era city walls (which you can bike or walk around), Lucca feels more like a quiet retreat than a tourist destination. I spent the day biking along the walls, exploring the old town’s quaint shops and cafes, and admiring the beautiful churches. If you’re looking for a place to experience Tuscan life without the crowds, Lucca is the perfect spot.
Pro Tip: Rent a bike and take a leisurely ride along the city walls to see the entire town from above. This guided e-bike tour comes with a winery visit and wine tasting. If you’re feeling adventurous, climb the Guinigi Tower for an incredible view of the city with its unique tree-topped rooftop.
9. San Galgano Abbey: A Mysterious Ruin
Distance: 86 km
Time: 1 hour 20 min by car
One of the most unique places I visited was the San Galgano Abbey, a Gothic ruin set in the rolling Tuscan hills. The abbey is famous for its roofless church, which creates an eerie and mystical atmosphere, especially when the sunlight filters through the arches. Legend has it that the sword in the stone, which inspired the Arthurian legend, is linked to this very spot. Visiting San Galgano felt like stepping back in time, and the setting was incredibly peaceful.
Pro Tip: Visit in the late afternoon when the light is softer, and the Abbey’s ruins take on a haunting, almost magical quality. Don’t forget to check out the nearby chapel, which is a bit of a hidden gem.
10. Bologna: A Food Lover’s Dream
Distance: 104 km
Time: 1 hour 20 min by car; 1 hour by train
If you’ve got a little more time and don’t mind a longer drive, a day trip to Bologna is an absolute must for food lovers. Bologna is known as the culinary capital of Italy, and I had the best pasta I’ve ever tasted there—hands down. From tagliatelle al ragù (what we outside Italy call “Bolognese”) to mortadella and the rich, creamy tortellini, every bite in Bologna was pure joy. The medieval architecture and vibrant student vibe make it a great city to explore on foot while sampling some of the best food in the country. Bologna is among the best day trips from Florence by train.
Pro Tip: Bologna is best experienced through its food markets. Head to the Quadrilatero area, where you’ll find traditional markets selling everything from cured meats to fresh pasta. Don’t skip the famous “Tortellini en Brodo”—a local delicacy! Read more about the best things to do in Bologna, Italy.
11. Montepulciano: Tuscany’s Wine Capital
Distance: 115 km
Time: 1 hour 30 min by car; 3 hours by bus
Montepulciano is a medieval hilltop town with spectacular views of the surrounding Val d’Orcia valley. Known for its Vino Nobile, a red wine that has earned the town a worldwide reputation, it’s the perfect day trip for wine lovers. I explored the town’s ancient streets, tasted the local wine at one of the underground cellars, and enjoyed a leisurely lunch in the Piazza Grande. The views here, especially at sunset, are beyond breathtaking. It is easy to visit Montepulciano from Florence by car. However, if you are not in Tuscany by car, you can tour wineries in Montepulciano and Montacino, and have lunch in stunning Pienza on this tour.
Pro Tip: To avoid the crowds, skip the busy summer months and visit in spring or fall when the vineyards are at their most vibrant. A tour of one of the historic wine cellars is a must! Read my guide to the best things to do in Montepulciano.
12. Arezzo: Art, Antiques, and Views
Distance: 82 km
Time: 1 hour by car; 1 hour by bus; 1 hour 30 min by train
Arezzo is one of Tuscany’s lesser-known gems but well worth a visit for its art, antiques, and picturesque views. I spent my day wandering through its lovely piazzas and exploring the stunning frescoes of Piero della Francesca in the Basilica di San Francesco. The antique market held on the first Sunday of each month is perfect if you love browsing through unique treasures. Arezzo is easily reachable from Florence by car, bus, and train.
Pro Tip: Visit Arezzo on the first weekend of the month for the famous antique fair. It’s one of the best places to find quirky, beautiful souvenirs. Read the ultimate guide to the things to do in Arezzo.
13. Cortona: Under the Tuscan Sun
Distance: 105 km
Time: 1 h 20 min by car; 1 h 50 min by train;
Made famous by Frances Mayes’ book Under the Tuscan Sun, Cortona is a town full of charm and elegance. Located in the hills of southern Tuscany, it offers sweeping views of Lake Trasimeno and the surrounding valley. I loved wandering its narrow streets, popping into art galleries, and grabbing a coffee at a local café. Cortona is a lovely day trip from Florence by car. If you don’t have an available car in Florence but wish to visit Cortona, consider taking this private tour of Assisi and Cortona from Florence.
Pro Tip: While in Cortona, visit Eremo Le Celle, a peaceful Franciscan hermitage set in the woods just outside town. It’s a serene escape and one of the most tranquil spots in all of Tuscany—perfect for a reflective moment or a quiet walk. Read my guide to Cortona, Italy.
14. Orvieto: The Hilltop Town with a Stunning Duomo
Distance: 170 km
Time: 2 h by car; 2 h 15 min by train; 2 h 40 min by bus
Orvieto is perched high on a volcanic hill in Umbria, offering one of the most scenic views in central Italy. The real gem here is the Orvieto Duomo, a cathedral with a stunning facade that’s worth the trip on its own. I spent my day wandering through the town’s cobbled streets, popping into artisan shops, and sampling local wines from the region. This tour makes visiting Orvieto and Assisi a wonderful day trip from Florence.
Pro Tip: If you have time, visit the Orvieto Underground, a labyrinth of caves and tunnels that date back to Etruscan times. It’s a fascinating journey into the town’s history!
Orvieto is one of the most beautiful towns in Umbria. Read more in my article about the best towns in Umbria.
15. Castiglione del Lago & Lake Trasimeno: Peaceful Lake Views
Distance:130 km
Time: 1 hour 30 min by car; 2 hours by train
Located on the shores of Lake Trasimeno, Castiglione del Lago is a charming medieval town with panoramic views of the water and the surrounding hills. I spent a peaceful afternoon walking around the town’s historic center and taking in the lake views, feeling miles away from the tourist crowds. It’s a wonderful spot for a relaxing lakeside picnic. Castiglione del Lago is one of the best day trips from Florence by train.
Pro Tip: Take a boat ride on Lake Trasimeno to visit the small islands of Isola Maggiore and Isola Polvese. They are incredibly peaceful and offer a different perspective on the lake.
16. Assisi: Spiritual Heart of Italy
Distance: 180 km
Time: 2 h min; 2h 30 min by bus; 3 h 40 min by train
Assisi is known worldwide as the birthplace of St. Francis, and visiting the town feels like stepping into a place of deep spirituality. I spent the day visiting the stunning Basilica di San Francesco and strolling through the peaceful streets of this UNESCO World Heritage town, which feels like it’s frozen in time. If not driving in Tuscany, you can visit Assisi and Orvieto from Florence on this tour.
Pro Tip: While the Basilica is a must-see, don’t miss the nearby Eremo delle Carceri, a hermitage set in the woods where St. Francis spent time in prayer. It’s incredibly serene and often much quieter than the main basilica. Read more about the 12 must-see attractions in Assisi, Italy.
17. Modena: Home of Balsamic Vinegar
Distance: 132 km
Time: 1 h 30 min by car; 1 h 10 min by train; 1 h 45 min by bus
Modena is known for its rich culinary heritage, particularly its balsamic vinegar. After visiting the beautiful Piazza Grande, I took a tour of one of the traditional vinegar houses to learn about the long process of making aged balsamic vinegar. Modena is also home to some of the best restaurants in Italy—definitely a food lover’s paradise. Modena is among the best day trips from Florence by car for gourmands. Need a car in Florence? Check out affordable rental cars here!
Pro Tip: Be sure to visit the Ferrari Museum in nearby Maranello if you’re a car enthusiast. It’s an easy addition to a Modena day trip!
18. Parma: A Taste of Italy’s Culinary Riches
Distance: 185 km
Time: 2 h 10 min by car; 1 h 45 min by train; 2 h 40 min by bus
Famous for its Parmigiano-Reggiano cheese, Parma is a delightful town for food lovers. I toured a local dairy farm to see how this iconic cheese is made, and of course, sampled plenty along the way. Parma’s elegant streets are also lined with beautiful palaces, making it a lovely destination for both history and food. Besides Bologna and Modena, Parma is the best day trip from Florence for foodies!
Pro Tip: Don’t miss the chance to try Prosciutto di Parma, the world-renowned cured ham. Pair it with some local wine for a true taste of the region.
19. Ravenna: Mosaics and Byzantine Beauty
Distance: 185 km
Time: 2 h 10 min by car
Ravenna is a UNESCO World Heritage site known for its breathtaking mosaics, which decorate the churches and mausoleums throughout the city. Take a day trip from Florence to Ravenna and marvel at the intricate designs, especially in the Basilica di San Vitale and Mausoleum of Galla Placidia. Ravenna feels a little off the beaten path, but its history and beauty make it a must-see. Ravenna is a great day trip from Florence by car for history lovers! If you are one of them, rent a car in Florence and head to Ravenna.
Pro Tip: Ravenna’s mosaics are best appreciated with a guide who can explain the intricate details and historical significance. It’s worth investing in a tour for a deeper understanding.
20. Bagno di Vignoni: A Thermal Village
Distance: 118 km
Time: 1 hour 30 min by car; 2 hours by bus
Bagno di Vignoni is a small medieval village known for its thermal waters and unique Piazza delle Sorgenti, a large thermal pool at the heart of the town. You can not bathe in the main square pool, but you can go to the Parco dei Mulini to relax in a spring of naturally hot water. Parco dei Mulini is free, no entrance ticket! I spent the day relaxing in the thermal waters, wandering through the narrow streets, and enjoying the tranquil atmosphere of this off-the-beaten-path town.
Pro Tip: Bring a swimsuit if you want to dip into the thermal pools or relax in the nearby hot springs. The town’s thermal baths are open year-round, but the atmosphere is especially peaceful during the off-season.
21. Cascate del Mulino di Saturnia: Natural Hot Springs
Distance: 190 km
Time: 2 h 40 min by car
If you’re looking for a truly relaxing experience, head to the Cascate del Mulino in Saturnia. These natural hot springs cascade down into pools surrounded by lush countryside. It’s a perfect place to unwind, soak in the warm water, and enjoy the beauty of Tuscany’s natural landscape. The hot springs of Cascate del Mulino di Saturnia are a little bit further from Florence. But, still manageable to visit if you are by car! Check out affordable rental cars in Florence here!
Pro Tip: Go early in the morning to avoid the crowds. The water temperature is perfect year-round, but in the cooler months, it’s especially magical.
Where to Stay in Florence:
- Luxury: Hotel Lungarno – If you want to wake up to views of the Arno River and feel like royalty, this place is for you. It’s steps away from major sights like the Uffizi Gallery and Ponte Vecchio, and you’ll be surrounded by art and luxury.
- Mid-Range: Hotel Spadai – A short walk from the Duomo, this hotel blends modern style with old-world charm. Bonus: the breakfast is amazing and private parking is available.
- Budget: Plus Florence – A super trendy and affordable option, especially if you’re traveling solo or with a group. They’ve got a rooftop pool, a bar, and an overall fun vibe.
Final Thoughts On Taking Day Trips From Florence
Florence might be the reason you book the trip—but these day trips are the reason you’ll keep thinking about it long after you leave.
Once you step beyond the city, Tuscany (and beyond) opens up in a completely different way. It’s in the quiet hilltop towns, the winding vineyard roads, the seaside villages, and the hidden thermal springs where Italy starts to feel more personal—and a lot more unforgettable.
After coming back to this region again and again, one thing is clear: you don’t just visit Florence—you use it as a gateway. A base for exploring, wandering, and discovering places that often end up outshining the city itself.
So take the detour. Rent the car. Hop on the train. Say yes to the extra stop.
Because the real magic of Florence?
It’s everything waiting just beyond it.
