If the art and architecture in Florence have the power to seduce you, then the vistas of the Tuscan region would charm you no less. Each town with a history dating back hundreds of years, where you could spend time indulging in La Dolce Vita. Tuscany has to be one of the most fabulous day trips from Florence to take. We explored the medieval towns of Monteriggioni, Siena and San Gimignano, and enjoyed an excellent wine tasting session. It would be superb to spend more time in this beautiful region, but a day trip from Florence to Tuscany is all that we had time for. A memorable day indeed.
Imagine this picture-perfect image – golden sun rays shining on a perfect landscape of rolling hills and gentle plains, interspersed with vineyards, olive groves, and tall cypress trees swaying.
I wish to go back to the Tuscan region someday and indulge in a week-long affair of farm-to-table fresh produce, excellent wines and quaint towns. But after exploring Florence in a day, we had another full day to explore Tuscany. It can be tough to figure which of the charming towns to explore in a day, but our decision was made easier after accounting for proximity to Florence city.
Here is my personal account of a delightful day in the Chianti region. Our day trip from Florence to Tuscany included Siena and the charming medieval towns of Monteriggioni and San Gimignano.
Stop 1: Day trip from Florence to Monteriggioni
For this day tour to Tuscany, I had booked a car and driver via Chianti drivers. It promised to be a more hassle-free experience than renting a car just for a day. The driver picked us up from our apartment in Florence and within a short while, the beautiful city of Florence gave way to the magical Tuscan landscape with vineyards and plains on both sides.
Our first stop was the medieval walled city of Monteriggioni. One step into the walled city and you are literally in the 13th century! The town hasn’t lost a shred of its medieval character. It is based on a hill and offers panoramic views of the landscape in all directions.
We walked all around the town, explored its quaint little shops for local produce and gelato. What a fun way to spend a morning enjoying the countryside under the blue open sky.
Stop 2: Day trip from Florence to Siena
A city that rivaled Florence in medieval times, Siena is a striking beauty. The heart of this beautiful city is the enormous Piazza del Campo, one of the biggest medieval squares in Europe.
A fantastic place to sit and watch life go by. The shell-shaped piazza is lined by cafes/restaurants on many sides. It has the imposing Torre del Mangia on one side. For the active and adventurous, climbing to the top of Torre del Mangia is possible. But with limited time on hand and having climbed the Giotto’s Campanile in Florence just the day before, no one was in a mood for this.
We roamed around the cobbled streets leading to the piazza and ate a leisurely lunch at a restaurant slightly away from the piazza. We also enjoyed the black and white Cathedral of Siena, which is as distinct and striking as Florence’s Cathedral. But the best part of the afternoon had to be lazying around at the Piazza del Campo and watching people. Kids having fun with water at a fountain, couples walking hand-in-hand or just enjoying a coffee at any of the myriad cafes. Folks taking a break from sightseeing and just sitting under the vast open sky.
Siena’s gothic architecture, rich history and traditions make it a must-see town in Tuscany. We enjoyed it for a few hours but it has enough attractions to keep you busy for a couple of days. You can visit the Palazzo Comunale that once hosted Siena’s council headquarters. Loggia della Mercanzia (the Merchants’ Storehouse) is another icon not to be missed.
Stop 3: Day trip from Florence for wine tasting
No visit to the Chianti region can be complete without tasting some of the wine produced here. And it was a perfect addition in our day trip from Florence itinerary to visit to Castello di Verrazano. A summer day in Tuscan countryside gives you unending views of green rolling hills. But enjoying a wine tour at an unhurried pace is a great way to experience Tuscany in winter as well.
Located in Greve in Chianti, midway between Siena and Florence, this trip to the Castle Verrazano fit in perfectly in our itinerary. The vineyards situated in Verrazzano are mentioned in a manuscript which dates back to 1150. How amazing is that!
We opted for the Classic Wine tour here, leisurely exploring parts of the castle and its gardens open to the public and then their historic aging cellars. Our guide from the Castle Verrazano took us through detailed information of grapes grown, the season for harvesting, the process followed for making the pulp and the wine, as well as the aging and bottling processes. This was followed by a short wine tasting session at the restaurant on the premises.
You also have the option of buying the bottles made from the grapes of this vineyard. Tuscany is the perfect place to buy wine, olive oil, truffles, cheese and other gifts of Italy.
Last stop: Day trip from Florence to San Gimignano
The last stop in our wonderful day trip from Florence to Tuscany was San Gimignao. If you ever wished for a fairytale, albeit in a medieval fashion, San Gimignano should be on your Tuscan itinerary. I am glad we chose to end the day trip to Tuscany with the evening walking past stone towers, ancient buildings and rustic architecture of San Gimignano. The historic center of this small walled town is a UNESCO World Heritage site.
The skyline of medieval towers makes San Gimignano very distinctive. You can see them rising from afar. This stunning skyline amidst green pains and vineyards made for a beautiful ending to our day. The charm of the town didn’t falter even when we entered it. There is one main road that cuts through the entire town and it is packed with tourists and boutique stores and lovely cafes.
We walked to the central square – Piazza del Duomo – where you can visit the Cathedral and see the various medieval towers. The only tower open to the public is the Torre Gross. But we were not up to climbing this tower and taking the scenic view. Instead, we just relaxed, soaked in the pleasant vibes, had a gelato, and did a lot of window shopping at the myriad leather, ceramic and food stores. I even bought a lovely pair of leather sandals.
Tuscan countryside is stunning enough to spend more than the day trip we managed from Florence. If you do decide to spend a few days here, there are plenty of options to stay in Tuscany from villas to castles.
Tuscany region also offers some incredibly fresh produce and best local Italian dishes to order. The wild boar meat is a delicacy cherished all over Tuscany. Pici is a delicious, hand-rolled pasta that originated in the Siena province. Another example of local cuisine is Panzanella, a Tuscan salad.
Planning a trip to Italy? Here are some more guides to help you plan your trip –
Italy Itinerary: The classic two-week Italy Itinerary
Italian cities: One day in Florence, 4 days in Rome, 2 days in Venice
Italian regions: Amalfi coast itinerary for 4 days, Capri 1 day itinerary, Lake Como in 3 days, Cinque Terre
Souvenirs: Good Souvenirs from Italy: Take Italy Home With You!
Food in Italy: 21 of the Best Local & Traditional Italian Food you must try
[This post was originally published in 2018, and later updated in 2024.]
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Have you visited Tuscany? Which is your favourite town or vineyard in Tuscany region? Share with us in the comments below.
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Hi! Did you do all of these in just one day? Need to the same but not sure if I can get to know Tuscany in just one day
We had limited time so booked a day trip to cover all this. It didn’t feel rushed but of course, it you have more time, Tuscany would be amazing. Or you could just cover 2 of the 4 spots we stopped at in a day.
I had been to Tuscany for 5 days and this was like taking a trip down the memory lane. Keep travelling
5 days seems so much better than our day out! What all parts did you explore?
I was all across the place. Spent couple of days in Barachhi vineyards and other places
Spending a day or more in a vineyard sounds fab. Hope to do it someday. But even a quick visit is worthwhile.