Day trip from Florence soaking the beautiful Tuscan landscape

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. It has to be one of the most fabulous day trips from Florence to take.

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What a stunning panorama. (Image credit: Pixabay)

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. The day trip included Siena from Florence and the charming medieval towns of Monteriggioni and San Gimignano.

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.

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You can see beauty as far as your eyes can see in all directions from this quaint town atop a hill.

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 under the blue open sky.

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.

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One of Europe’s greatest medieval squares.

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.

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Look at this black and white beauty!

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.

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 itinerary to do a visit to Castello di Verrazano.

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! 

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A classic vineyard scene from Tuscany. (Image credit: Pixabay)

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.

Day trip from Florence to San Gimignano

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. 

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One of the most perfect medieval towns you will visit in Tuscany.

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. 

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You can amble through the entire town from one end to the other in less than 1/2 hour.

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.


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One of the most fabulous day trips to take from Florence has to be to the Tuscan region. Our itinerary included exploring the striking city of Siena, the medieval towns of Monteriggioni and San Gimignano and having an authentic wine tasting session at a vineyard. #italy #daytripfromflorence #tuscany #siena #monteriggioni #chianti #winetasting #sangimignano              One of the most fabulous day trips to take from Florence has to be to the Tuscan region. Our itinerary included exploring the striking city of Siena, the medieval towns of Monteriggioni and San Gimignano and having an authentic wine tasting session at a vineyard. #italy #daytripfromflorence #tuscany #siena #monteriggioni #chianti #winetasting #sangimignano


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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Author: Shweta Singhal

Hi! I am Shweta, the zest behind this blog . I play several roles – parent to a 6-year old, adventure enthusiast, travel blogger, generally open to trying out new things in life. Besides travel, I love books and theatre and art. I would love to hear from you; do drop a comment. Join me on Instagram / Twitter @zestinatote.

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