Tuscany in One Day Itinerary: Siena, Chianti, San Gimignano, Pisa

Seeing all of Tuscany in one day is impossible. But what about seeing the highlights on a Tuscany day trip? Now that’s a different story!

Departing from Florence, you can discover the best of Tuscany in just one day. From the beautiful, culture-rich city of Siena and the rolling hills and vineyards of Chianti, to the enchanting medieval hilltop town of San Gimignano and the Leaning Tower of Pisa, endless Tuscan magic awaits! 

All up, I’ve spent weeks in Tuscany, road-tripping to the cutest towns, discovering the most beautiful landscapes, and wine-tasting at family-run vineyards… So I can confirm: your Florence itinerary will be hopelessly incomplete without spending one day in Tuscany!

In this post, you’ll discover how to see the best of Tuscany in one day – whether you want to book a guided Tuscany day trip or explore on your own!

Can You See Tuscany in One Day?

Tuscany is a large region. So, no, you can’t see all of Tuscany in one day. However, there’s a small pocket of Tuscany that provides an excellent snapshot of the region.

On a well-planned Tuscany tour (departing from Florence), you can easily visit all of these bucket-list destinations in one day: 

• Siena: Home to a jaw-dropping masterpiece of a Duomo, centuries-old horse-racing culture, and fascinating history (including a long-standing rivalry with Florence!), you’re going to love Siena.
• Chianti: Family-run vineyards, olive groves, sunflower fields, cypress trees, and old terracotta-colored farmhouses are scattered throughout this gorgeous wine region. A delicious farm-fresh lunch and wine tasting await you here!
• San Gimignano: This charming fortified town, perched high on a hilltop, is a UNESCO World Heritage Site, featuring the world’s best gelato shop, 14 medieval watchtowers, cute boutiques, and incredible views of the Tuscan countryside. 
• Pisa: Ever heard of the iconic Leaning Tower of Pisa? Enough said! 

Sounds like an amazing day, right? Let’s discuss how to see the highlights of Tuscany in one day!

SPOILER ALERT: Book this Tuscany Day Trip from Florence. I’ve been on this tour twice and highly recommend it! Or, read on for my self-guided itinerary and expert tips!

READ MORE: 10 Incredible Day Trips from Florence + Must-Know Tips

Guided Tour of Tuscany in 1 Day vs. a Self-Guided Trip

The options for day trips from Florence are endless. But if you’re set on seeing Siena, Chianti, San Gimignano, and Pisa in one day, then I think this guided day trip is the best option.

On this guided tour, everything is organized for you – from roundtrip transportation, tickets to the Duomo di Siena, and guided historical walks, to wine-tasting and a delicious lunch… Which means your day trip will be fun, enriching, and completely stress-free.

I have been on this Tuscany Day Trip twice and wholeheartedly recommend it. Click here to book it.

When it comes to self-guided day trips through Tuscany, well, hear me out… I love exploring on my own. But one day isn’t enough time for that.

Just picking up and dropping off a rental car can waste two of your precious hours. Plus, your itinerary will be bound by the rental office’s opening/closing times – and you’ll have to spend on taxi fares there/back. And, as you explore, you’ll waste time in ticketing lines for attractions like the Duomo di Siena, figuring out driving directions, coordinating lunch and wine-tasting, etc. 

Also, before you ask, no, public transportation is not a viable option for one day in Tuscany if you want to see Siena, San Chianti, San Gimignano, and Pisa… However, if you just want to take a day trip from Florence to Siena via train or bus, that’s a great alternative and totally doable; there are enough things to do in Siena to occupy a whole day!

HOT TIP: This Tuscany Day Trip from Florence is extremely popular and sells out; book it now with free cancellation to avoid missing out. 

About the Tuscany in One Day Guided Tour

Ready to explore the best of Tuscany? Without having to worry about lunch, which sights and attractions you might glance right past, and if that 15-minute line is worth the wait…?

My favorite full-day guided tour of the Tuscany region starts and ends in Florence. On this full-day tour (it’s 12 hours long!), you’ll explore three mesmerizing UNESCO World Heritage Sites: Siena, San Gimignano, and Pisa.

Plus, you’ll enjoy a delicious, traditional lunch and drink (lots of!) wine at a family-run farm in the Chianti region.

Along the way, you’ll savor incredible views of the Tuscan countryside – as you travel in a comfortable, air-conditioned coach.

You’ll hear folk tales. and legends, learn about Tuscany’s rich history, and listen as your local guide points out the smaller details you’d likely otherwise miss. (Who would want to walk past Michelangelo’s first-ever self-sculpture without realizing it!?)

1 Day in Tuscany Tour: Itinerary Overview

Here’s a step-by-step overview of how the guided Tuscany Day Trip goes!

• But first, coffee! Just a short, ten-minute walk from the meeting spot for your Tuscany Day Trip, stop by my favorite coffee shop in Florence for an espresso and a pastry: Ditta Artigianale Mercato San Lorenzo.
• Meet the tour leader of your Tuscany Day Trip at the Santa Maria Novella Train Station in Florence at 7:45 AM.
• The air-conditioned coach departs around 8 AM heading to the first stop, Siena.
• Enjoy a few hours in Siena; you’ll go on a historic walking tour with a local guide and visit the iconic Duomo di Siena. Before you go, have an espresso, shop for souvenirs, and try Panforte di Siena (fruitcake).
• Next, you’ll travel to Fattoria Poggio Alloro for a vineyard/farm tour, abundant wine tastings, and a decadent Tuscan lunch.
• After a short 15-minute drive, you’ll explore the medieval center of San Gimignano and enjoy world-famous gelato!
• Back on the bus, you’ll travel through the Tuscan countryside (for about an hour) to Pisa.
• Admire the highlights in Pisa; choose to climb up the Leaning Tower or meander on your own. 
• Return to Florence around 8 PM – just in time for dinner!

Self-Guided Tuscany in One Day Itinerary

Want to go on your own? Here’s your self-guided 1-day Tuscany itinerary!

• Book a rental car. I recommend this website for the best prices and availability. 
• Taxi to the rental car office around 7 AM for an 8 AM pickup.
• Siena: Travel to Siena, park here, and spend about three hours exploring the city center, Piazza del Campo, and the Duomo di Siena. Climb up the main tower, Torre del Mangia, for a panoramic view of Siena and the countryside. I’ve been on this guided walking tour of Siena and it was excellent; plus, it includes Duomo tickets!
• Wine tasting and lunch: Around 12 PM, jump back in the car and head through the rolling hills to Foresteria Villa Cerna for a traditional Tuscan lunch and wine tasting. Another option is this wine and food tasting in an organic family winery near San Gimignano. 
• San Gimignano: Continue further to the beautiful town of San Gimignano for award-winning gelato and to explore inside the medieval walls. Park here.
• Pisa: Around 3 PM, make the 75-minute drive to admire the Leaning Tower of Pisa and other monuments in the city center. Park here. OR skip Pisa and spend more time in the other three destinations!
• Head back to Florence to return your rental car.

Must-Know Tips for Driving in Tuscany

After renting numerous cars in Italy, there are few things to consider before getting behind the wheel:

• Arrive at the car rental office in Florence as soon as it opens to avoid waiting in line. I’ve had to wait over an hour in Florence for my car… not a great start to one day in Tuscany!
• Plan carefully where you’ll park; you can’t drive into or park inside the city centers of Siena, San Gimignano, or Pisa; they are Zona Traffico Limitato (ZTL) zones (pedestrian-only zones that only residents can drive into). ZTL signs are not always obvious and Google Maps does not avoid active ZTL zones. You will be fined if you drive into one.
• Make sure you have your normal driver’s license and an international driver’s license; if you drive without one, you risk a hefty fine of around €280 (and yes, I’m speaking from unfortunate personal experience!).

Best Destinations for 1 Day in Tuscany

Okay, let’s dive deeper into the best destinations to see during one day in Tuscany! If you go on this Tuscany Day Trip from Florence, this is what you can expect to see and do! 

Siena

The drive to Siena from Florence takes just over an hour through the beautiful rolling Tuscan hills. It’s a stunning city, featuring a seashell-shaped plaza (Piazza del Campo), medieval walls and towers, and a super-rich cultural background. 

During my Tuscany day trip, a local Sienese tour guide walked us through Siena, telling us all about Siena’s history, traditions, and culture – including the famous Palio di Siena.

The Palio di Siena is a bi-annual horse race that’s held in the Piazza del Campo (pictured above). The city’s 17 contrade (or districts) compete against each other – and they have been, since at least the 6th century!

Palio takes place twice yearly (on July 2nd and August 16th), filling the air with infectious excitement and joy. It’s all the Sienese think, talk, and care about…

People come from all over the globe to experience this medieval tradition, complete with a parade, horse-blessing ceremony, flag throwing, historical costumes, and of course, the horse race itself. The 2023 race was a memorable one; take a peek!

Aside from Palio, Siena is one of the most charming cities you’ll ever visit.

As you walk through the streets and alleys of Siena, you’ll notice the brightly colored shutters, the centuries-old buildings, a sense of extreme Sienese pride emanating from every local (in a good way), and flags and decorations signifying the different contrade.  

The main highlight of Siena, though, is the Duomo di Siena, regarded as one of Italy’s most beautiful Romanesque-Gothic cathedrals. 

Every surface of the Duomo di Siena, inside and out, is adorned with something intricate and dazzling… From the elegant marble floors and the green-and-white-striped pillars, to the incredible works by world-renowned artists like Michelangelo, Donatello, Pinturicchio, and Pisano and the library filled with centuries-old scrolls and frescos, you’ll be blown away!

Wine Tasting & Lunch in Chianti 

After Siena, you’ll drive out to Fattoria Poggio Alloro, a gorgeous agriturismo in the Chianti region. 

Upon arrival, we walked through the vineyards, learned about olive oil and wine-making processes, and savored the views of the rolling hills.

And then came the best part! Is there anything in this world better than a long, leisurely Italian lunch? (No.)

Both times I visited, the menu featured olive oil from the farm, freshly baked bread, cured salami and prosciutto, local cheeses, garden salad, homemade pasta Bolognese, and a lot of wine. Everything came from the family’s land, and it was all heavenly.

The staff at the vineyard also gave us an informal wine-tasting lesson on the four different wine varieties we tried.

To this day, after many trips to Italy, this experience still sticks out in my mind!

San Gimignano

There are so many reasons to visit San Gimignano, the “Manhattan of Tuscany.” It’s an enchanting hilltop town, full of medieval towers, that positively oozes charm.

As you stroll, you’re bound to feel like you’ve traveled back in time…

The trick to achieving this, though, is to stray from the main piazza and shopping street – that’s congested with tourists mid-day – until you find some quiet alleys to wander in peace.

All the stone buildings share gorgeous creamy hues, the cobblestone-laden alleyways are adorable, and the panoramic views of the surrounding countryside are breathtaking. 

And, also, I can confirm: stopping by the cathedral is worth it for the 14th-century frescoes and the stunning views from the medieval tower!

But one of the most important reasons to visit San Gimignano involves an Italian dietary staple: gelato.

Gelateria Dondoli, which stands proudly in the town’s Piazza della Cisterna, is a winner of the Gelato World Championship! Some say that Master Gelato Maker, Sergio Dondoli, makes the world’s best gelato; and I can’t disagree!

I’ve been to Gelateria Dondoli many times, so I’ve tried about 20 of Dondoli’s signature flavors. As you can imagine, they’re all ridiculously delish! 

Pisa

The Leaning Tower of Pisa symbolizes Tuscany – and Italy as a whole. The Tuscany Day Trip from Florence includes Pisa, so you’re about to see it with your own eyes!

After a short drive through the iconic Tuscan countryside, we had about an hour to roam the peaceful city center of Pisa, climb the Leaning Tower of Pisa, and see the Piazza del Duomo (Piazza dei Miracoli – a UNESCO World Heritage Site), on our own.

And finally, we headed back to Florence. What an epic day!

HOT TIP: If you want to climb the tower, make sure to select the “Full Tour + Leaning Tower Tickets” option! Click here to book it.

Final Thoughts: One Day in Tuscany

In conclusion, I can’t recommend booking this Tuscany Day Trip of Siena, San Gimignano, Pisa, and Chianti enough. 

Important details:

• Departs from Florence daily, at 8 AM, in an air-conditioned vehicle
• Visits include Siena, a winery in Chianti, San Gimignano, and Pisa (with free time!)
• Includes a guided walking tour of Siena and entry into the Duomo
• About 12 hours long
• Around $150 per person (including the winery lunch)

Click here to book your Tuscany Day Trip to Siena, San Gimignano, Pisa, and Chianti.

1-Day Tuscany Itinerary: FAQs

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Maddy’s Avenue experienced the Best of Tuscany Tour as guests of Walkabout Florence, but as always, all opinions are our own! I believe 100% you will love this tour!