Tuscany Day Tour: Visit Siena, San Gimignano, and Chianti in One Day

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The Tuscan countryside is simply stunning. And taking a Tuscany day trip to experience the lush rolling hills, medieval hill towns, delicious food, and wines is an experience not to be missed.

While in Florence, exploring the local food and wine specialties, we teamed up with Walks and their sister company, Devour Tours for a day trip in Tuscany.

If you are looking for a Tuscany day tour beyond Florence, read on. In this review, we highlight our experience and share our overall impressions. 

Here’s what to expect on a Tuscany day trip from Florence.

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Tuscany Day Tour Itinerary

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Comfortable van for a Tuscany day trip

Early one Saturday morning, we met our group in the center of Florence, excited for our Tuscany day trip from Florence.

Pia, our tour guide, warmly welcomed the group and outlined the agenda for the day. The Tuscany day trip was to Siena, Chianti, and San Gimignano. Lunch was at a traditional Chianti winery along with wine tastings.

Just as we were about to leave, more people joined the group due to a booking mix up. Even so, the group was still a manageable size of fourteen, keeping the experience intimate.

The day Pia told us was organized around structured and free time. And, as she put it, it was to be “a day of sitting back, relaxing, and getting to know the Tuscany region and Chianti wines.”

Our group of 14 was split into two comfortable vans, and we were off to a fun-filled wonderful day of exploration.

AUTHENTIC FOOD QUEST TIP: This well-paced Tuscany day tour from Florence starts at 8:30am and takes you on a full day trip in Tuscany. Prepare to see a lot, sip fine wines and eat more than you need. You will be back by 6pm or so, enough time for a nice evening in Florence.

Highlights Of Our Tuscany Day Trip

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View of Florence from the Piazza Michelangelo

From the center of Florence, we took a short drive to Piazza Michelangelo for stunning views overlooking the city.

Admiring the iconic red rooftops and historic landmarks was just the beginning of a day filled with lush rolling hills and picturesque medieval towns.

From each of the cities we visited and the Chianti region, we share our favorite highlights from our day trip to Tuscany from Florence.

Siena: The Medieval City of Art

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After a cloudy start, Siena welcomed us with blue sky and medieval charm

Siena, a stunning medieval city and Unesco World Heritage Site, immediately captivated us with its narrow streets and well-preserved imposing monuments.

Built on three hills, you want to be prepared with comfortable shoes as you admire the city’s beauty.

After a short bathroom and coffee break we embarked on a walking tour of Siena. We stopped at different points of interest, learning about this famous city and its rich history.

Piazza del Campo – The Heart of Siena

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Medieval Torre del Mangia

One of the things Siena is most famous for is its horse races, known as the Palio di Siena. These horse races take place twice a year and draw crowds from around the world.

Standing in the breathtaking Piazza del Campo, a shell-shaped square where the horse races take place, our guide, Pia, regaled us with fascinating stories about Siena’s past, the horse races, and the city’s rivalry with Florence.

Learning about the contradas, the world’s oldest bank, and the ties to Rome was a window into the city’s fascinating history.

Siena Cathedral – Stunning Gothic Cathedral

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Siena Cathedral is a masterpiece of Gothic architecture

Our final stop on our guided tour of Siena was at the stunning Gothic Siena Cathedral, or Duomo di Siena. 

This is one of the most beautiful cathedrals we’ve ever seen. Designed by some of Italy’s finest artists, we were in awe of its beauty and intricate details.

At this point on the tour, we were then given one free hour to explore further. 

Before the group dispersed we were armed with recommendations for other must-see Siena sights and Sienese local specialties to try.

Siena Traditional Sweets – Must Try Treats

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Siena’s traditional almond cookies you must try

With our return meeting point clearly defined, we spent our free time walking through the streets and discovering hidden gems around every corner. 

We even stumbled upon a chocolate fair and couldn’t resist buying some artisanal chocolate.

One of the specialty sweets from Siena that we tried were traditional almond cookies called Ricciarelli alla mandorla. 

These were delightful, chewy and not too sweet almond cookies that we are glad to have discovered.

With our Tuscany day trip in Siena off to a great start, we were eager for what was to come.

At this point, hungry and ready for lunch, we were excited for our next stop at a Chianti winery for a traditional Tuscan lunch.

RELATED: The 9 Best Wine Tours From Rome For Wine Tastings and Sightseeing

Chianti Winery Visit

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Scenic view from the Chianti winery

Castellina in Chianti, near Siena, was the location for our winery lunch and wine tasting.

The family owned winery was set on a hill with picturesque views of the surrounding countryside.

It was windy and chilly when we arrived and we didn’t have time to visit the vineyards. If you visit in the warmer months, we highly recommend spending time outdoors.

Warmly welcomed by the winery staff, we started with a short guided tour of the winery cellars. Then we had an overview of the Chianti wine production method.

AUTHENTIC FOOD QUEST TIP: When visiting the Chianti, you might want to bring bottles of wine home safely with you. Consider any one of these best wine suitcases for safe and easy travels.

Chianti Wine Tastings

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Three delicious Chianti wines with lunch

Ready to eat, a well laid-out table awaited us. While sipping on a welcome glass of sparkling wine and a Tuscan antipasti platter, we learned more about Chianti and the different wines.

As our guide from the winery talked about Chianti’s long history and cultural significance, we tried two different Chianti wines to understand the subtleties. 

Along with the wines, we also tasted different aged Balsamic Vinegars and extra virgin olive oil produced exclusively by the winery.

The wine tastings continued, including a paired Super Tuscan wine from the winery, which was a nice balance to the Chianti wines.

In total, the wine tastings comprised about five local wines, including the sparkling and dessert wines. 

If you are interested, wines from the winery and vinegars are available for purchase. Some people in our group bought some wine to take home with them.

RELATED: 10 Must-Try Food Tours of Florence To Explore the Local Cuisine

Traditional Tuscan Cuisine

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This tasty Tuscan Ragu pasta was an absolute delight

Lunch was one of the highlights of our Tuscany day trip. After starting with the large antipasti platter, two options for the main meal, one meat, and one vegetarian were offered.

Most of the group chose the meat option which was a traditional Tuscan Ragù or meat sauce with pappardelle pasta.

The Tuscan-Style ragu was particularly delicious and an instant favorite. Full of flavor and hearty, it complemented the local wines.

After cleaning our platter with a simple salad served with the winery local vinegar, it was time for dessert.

One of the most famous Tuscan desserts, Cantucci and Vin Santo ended our multi-course Tuscan lunch.

This duo of Cantucci (traditional almond cookies) and Vin Santo, which translates to Holy Wine, was a nice sweet finish to our traditional Tuscan lunch.

If you are not a wine lover, there is no obligation to finish your wines. The amount served is enough to allow you to pace yourself for the walking tour in San Gimignano, the last medieval hill town on the tour.

San Gimignano –  A Medieval Hilltop Town

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San Gimignano skyline is adorned with medieval towers

San Gimignano surprised us. A walled city known for its towers, our guide affectionately referred to it as a “medieval New York City.”

This Unesco World Heritage site is visually striking, with medieval towers dotting its skyline.

The city, we learned, once had as many as 72 tower houses, a symbol of wealth and power in the middle ages.

Today, only about 14 have survived rising as high as 160 feet (50 m) above Tuscany’s surrounding countryside.

A Unesco World Heritage Site, San Gimignano was also a rest stop on The Via Francigena, an ancient European pilgrimage route.

San Gimignano Highlights – Piazza della Cisterna and Torre Grossa

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While walking up one of the towers to see the stunning scenery, we passed through Piazza della Cisterna, a picturesque square, learning about the old well in the center.

From Torre Grossa, a medieval tower, we enjoyed views of the beautiful Tuscan countryside. 

Looking out, we were transported to another time. Awed by Tuscany’s timeless beauty.

The World’s Best Gelato in San Gimignano

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The best gelato – a perfect treat to end the day tour

During our free time in the medieval hill town, it was highly suggested by Pia, our guide to stop for Gelato from a world-renowned Gelateria.

In the main square are two gelateria’s, each claiming to have the best gelato in the world. The recommendation was to go to Gelateria Dondoli which holds the “gelato world champion” title for multiple years. 

Choosing two traditional flavors, cantucci and saffron, we savored the gelato. But, is it the best gelato in the world? We’ll let you decide on your Tuscany day trip.

From San Gimignano, we enjoyed a scenic drive back to Florence city centre. We arrived at about 6:00 pm with plenty of time to see more Florence and have dinner.

Tips for Making the Most of Your Tuscany Day Tour

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You can pick up souvenirs in San Gimignano
  • Dress in layers – Temperatures in Tuscany’s medieval towns can be cooler than in Florence. Depending on what time of the year you visit, you want to be well prepared. In March, when we took our tour, it was chilly in the morning and layers help. In the warmer months pack your hat, sunscreen and don’t forget water.
  • Choose The Best Time of the Year to Visit Tuscany – Tuscany is beloved and gets visitors all year round. During the peak summer months, you’ll find plenty of tourists. For a quieter experience, visit during the lower season from November to February. Though expect the weather to be chilly. The shoulder season in March and October are comfortable with less tourists. Our visit during the months of March and April were comfortable with not too many tourists.
  • Make Reservations in advance –  Regardless of the time of year you visit Florence and if you want to take a Tuscany day tour, book it in advance. The Tuscany region and Chianti countryside are popular excursions and tend to get booked in advance.

AUTHENTIC FOOD QUEST TIP: Make your culinary travels worry-free! With the right travel insurance, you’ll enjoy a delicious experience. From medical emergencies, flight cancelations, car rental protection, or tour cancelations, a good travel insurance has got you covered. Check out our travel insurance review for food lovers to get started.

Overall Impressions of this Tuscany Day Trip

What We Loved

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This Tuscany day tour has a lot to offer

Getting out of Florence and seeing more of the stunning Tuscan countryside is what we loved most about our day tour from Florence. 

This was our first time visiting the cities of Siena, Chianti, and San Gimignano, and we loved the experience. More specifically, we enjoyed;

  • The convenience of seeing a lot in one day – This Tuscany day tour was well-paced with the towns located about an hour apart. This made it convenient to see 3 iconic cities without feeling rushed. Not having to worry about driving and parking a car in narrow medieval streets made the day tour even more enjoyable.
  • Brief introductory history of each city – Our guide was excellent and a walking encyclopedia of Tuscan history and traditions. The guided walking tour we had in each city made for an enriching experience.
  • Traditional Tuscan lunch and Chianti wine tasting – Being in one of Itay’s most important wine regions, it was great to visit a family-owned winery in Chianti. The Tuscan lunch with traditional specialties along with the different Chianti wine tastings was our favorite part of the experience.
  • Free time to explore – We loved having free time to explore each city at our own pace. With the tips and recommendations offered by our tour guide, we liked knowing the key parts to visit and local foods to try.
  • Scenic drive through Tuscany’s countryside – With a designated driver at the wheel, we were able to relax and take in the stunning scenery of rolling hills, cypress trees, vineyards, olive groves, and medieval towns.

What Could Be Improved on this Tuscany Day Trip

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There is much to learn about Chianti wines

Overall, there was not much that can be improved about this Tuscany day trip. This full day tour through the Chianti wine region delivered on all fronts, though left us wanting more.

  • More time in Siena – We would have loved to spend more time in Siena as there was much to do and see. While the guided tour through the city was well-paced and we had free time, we left plotting a return visit independently.
  • More time in the Chianti wine estate –  As wine lovers, we would have liked time at the local winery visiting the vineyards and diving into the Chianti wine production process. While the tour is not dedicated to Chianti wine tastings, we left with a desire to further explore the Chianti wine region.

RELATED: 12 Best Chianti Wine Tours From Florence For Wine Tastings and Sightseeing

How To Book Your Tuscany Day Trip

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Siena is a must-see while in Florence

A Tuscany day trip from Florence is one of the best tours to experience the stunning Tuscan hills, charming medieval villages, amazing food, and world-class wines. 

This full day tour with round trip transport provided offers the perfect combination of sightseeing, history, and food and wine. 

With a knowledgeable tour guide, you’ll discover more about the cultural heritage, cuisine, Chianti wine, and more.

Get more from your trip to Florence with a Tuscany day trip.

Other Tours in Florence and Tuscany to Consider

Florence Food and Wine Tour

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Taste the flavors of Florence

If you don’t have time for a Tuscany day trip but want to sip on Chianti wines and learn about the food culture in Florence, consider this tour instead.

This Florence food and wine tour takes you across the Arno River to the local Oltrarno neighborhood for food and wine tastings at family-owned eateries.

We took this tour and loved the stops for Italian aperitivo and delicious Chianti wines. One of the highlights was digging into Bistecca alla Fiorentina, or Florentine steak with exquisite wine.

The about 3.5 sunset tour ends with some of the best gelato we’ve enjoyed in Florence.

What To Expect From This Food and Wine Tour

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Savor Chianti wines with delicious dishes
  • Enjoy more than 8 food and wine tastings at hidden local gems in Oltrarno
  • Discover the wine windows in Florence and sip wine straight from the windows
  • In the company of a local guide, explore the vibrant and local Oltrarno neighborhood
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Have you ever taken a day trip in Tuscany? If so, which towns or regions did you visit? Please let us know in the comments below.

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Special thanks to Walks and Devour Tours for having us on this Florence to Tuscany day trip. All views and opinions expressed are our own. Full bellies and happy taste buds too.

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