If you’re in Florence and have a day to spare, this is the perfect opportunity to experience more of what Tuscany has to offer. We joined a day tour with Ciao Florence that took us from the medieval walls of Monteriggioni to the historic streets of Siena, through the picturesque Chianti Hills for a wine tasting, and finally ended in the charming town of San Gimignano. It’s an ideal way to see some of the region’s most iconic sights and get a taste of the Tuscan countryside—literally! In this blog, we’ll break down the highlights of our journey and show you why this trip is a must for anyone looking to explore the best day trip from Florence.
Starting Point: Piazzale Montelungo, Florence
Our day began at Piazzale Montelungo, where Ciao Florence tours depart. It’s an easy walk from Florence’s city center, taking about 20 minutes, making it a convenient starting point. The route is straightforward and allows you to enjoy some of the city’s sights before starting your journey.
First Destination: Monteriggioni
The first destination was Monteriggioni, a small medieval town enclosed by well-preserved stone walls and 14 towers. Built in the 13th century, this tiny village is like a snapshot of Tuscan history. You can walk along the cobbled streets, explore the quaint shops, or even climb parts of the wall for panoramic views of the Tuscan countryside. Though it’s a short stop, it’s a great introduction to Tuscany’s charm and history before moving on to the day’s next highlight.
Exploring Siena: A Medieval Gem
After leaving Monteriggioni, we made our way to Siena, a city bursting with medieval history and character. The drive itself was scenic, with rolling hills and classic Tuscan landscapes setting the mood. Once we arrived, our guide led us through the historic center—a UNESCO World Heritage site—and it felt like stepping into another era. The city is built on three hills, giving it a unique layout with winding streets and alleys that all seem to lead to the main square, Piazza del Campo.
Piazza del Campo is famous for its shell shape and the Palio, a historic horse race held twice a year. This race is a big deal for the city, with 17 different districts of Siena competing against each other, making it a vibrant and lively event if you happen to be there during the summer months. Around the piazza, you’ll find cafes, restaurants, and plenty of spots to soak in the atmosphere.
One of Siena’s most stunning landmarks is the Siena Cathedral, or Duomo. This Gothic masterpiece is striking with its black and white striped marble exterior. Inside, you’ll find intricate mosaics, frescoes, and sculptures by some of Italy’s most famous artists, including Michelangelo. It’s also possible to climb to the top of the cathedral for some impressive views of the city.
Siena has a unique charm—less crowded than Florence, yet filled with just as much history and culture. The tour gave us time to explore the main sights, try some local food, and really take in the atmosphere of one of Tuscany’s most iconic cities.
Wine Tasting in the Chianti Hills
From Siena, we journeyed into the picturesque Chianti Hills, a region famous for its rolling vineyards, olive groves, and some of the best wine in Italy. The drive alone is worth the trip, with winding roads that reveal stunning views of the countryside around every bend. Our stop was a local winery, Agricola Poggio ai Laghi, where we got a taste of authentic Tuscan hospitality.
Here, we learned about the winemaking process—from grape harvesting to fermentation and aging. But of course, the main highlight was the wine tasting itself. We sampled a variety of Chianti wines, including the classic Chianti Classico—known for its robust flavor and distinctive black rooster seal—as well as some local olive oil and cured meats. The winery’s rustic setting, surrounded by vineyards and set against the backdrop of the Tuscan hills, made it a truly memorable experience.
For those who appreciate good wine and want to see the more relaxed side of Tuscany, this part of the tour is a must. It’s not only a chance to enjoy incredible wine but also to learn about the history and traditions that make the Chianti region so special.
San Gimignano: The Medieval Manhattan
After indulging in the flavors of the Chianti region, our final stop of the day was San Gimignano, often referred to as the ‘Medieval Manhattan’ because of its striking skyline of tall stone towers. This town is a UNESCO World Heritage site and has managed to preserve much of its original medieval architecture, making it one of the most picturesque towns in Tuscany.
Walking through the gates of San Gimignano feels like stepping back in time. The main street, Via San Giovanni, is lined with artisan shops, gelaterias, and cafes, leading up to the heart of the town, Piazza della Cisterna. This triangular square is the perfect place to stop for a break and enjoy some gelato—which, by the way, you can get at Gelateria Dondoli, often called the best gelato in the world.
San Gimignano is also known for its impressive towers—originally, there were 72, but today, 14 still stand. Climbing Torre Grossa, the tallest tower in town, offers incredible panoramic views of the surrounding countryside. The town also has several churches, like the Collegiate Church of San Gimignano, with its frescoes that provide a vivid look into the religious art of the time.
We were given some free time to explore, shop for local products like saffron and Vernaccia wine (a local white wine), and just take in the relaxed atmosphere of this hilltop town. It’s the perfect way to end a day trip around Tuscany—combining history, views, and a taste of authentic Tuscan life.
Wrapping Up Our Tuscan Adventure
With San Gimignano as the final stop, we wrapped up our journey through Tuscany and headed back to Florence. The return trip allowed some time to reflect on the day’s highlights—from the historic charm of Monteriggioni, the vibrant culture of Siena, the flavors of Chianti, to the medieval beauty of San Gimignano. Each stop had something unique to offer and gave a glimpse into the rich history and culture of this stunning region.
The tour by Ciao Florence really makes it easy to see a variety of places in one day without feeling rushed. If you’re in Florence and want to experience more of Tuscany but have limited time, this kind of day trip is a fantastic way to make the most of your visit. You get a mix of history, culture, wine, and beautiful landscapes—all the best parts of Tuscany rolled into one day.
So, whether you’re a history buff, wine enthusiast, or just looking to explore the Tuscan countryside, this tour covers it all. Hopefully, this guide helps you decide whether to add this day trip to your Florence itinerary. If you’ve been on a similar tour or plan to, let me know in the comments—I’d love to hear your thoughts! And if you found this blog helpful, don’t forget to subscribe for more travel content.
Frequently Asked Questions
1. How long is the day trip from Florence?
The day trip lasts about 10-12 hours, departing in the morning and returning in the early evening, allowing enough time to explore each destination without feeling rushed.
2. Do I need to book the tour in advance?
Yes, it is recommended to book the tour in advance, especially during peak tourist seasons, as spots can fill up quickly.
3. Is the tour suitable for children?
Yes, the tour is suitable for children, although the wine tasting is obviously more geared towards adults. Children will enjoy exploring the medieval towns and the scenic drives.
4. What should I bring on the tour?
Comfortable walking shoes, a camera, water, and some cash for purchasing local goods or enjoying a meal are recommended. Sunscreen and a hat are also useful during the summer months.
5. Can I join the tour if I have dietary restrictions?
Yes, most tours, including the winery, are accommodating of dietary restrictions, but it’s a good idea to inform the tour operator in advance.
6. Is there a lot of walking involved?
There is a fair amount of walking involved, especially in Siena and San Gimignano. The walking is generally at a leisurely pace, but comfortable footwear is essential.
7. Are entrance fees included in the tour?
Most tours include entrance fees to the main attractions, but it’s always best to check with the tour provider to avoid surprises.
