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8 BEST Siena Tours from Florence (by an Italian)

Eager to explore the best of Tuscany? The city of Siena ought to be at the top of your list! In this post you’ll find the ultimate Siena tours from Florence for a memorable trip. Check them out!

Siena is one of the most popular destinations in Tuscany, and it’s no wonder why. This enchanting city boasts a rich history, stunning architecture, and vibrant culture. I personally love its charming streets, medieval buildings, and unique attractions!

These include the famous Piazza del Campo and the Gothic-style Siena Cathedral, the two major landmarks. However, you’ll also find plenty of restaurants, cafés, and shops, along with great architecture.

Siena is also a hotspot for tasting the region’s delicious cuisine, and for shopping locally-made products. In a nutshell, you can’t get bored in this city!

Florence, located 50 miles (80 km) from Siena, is the perfect base to explore the Tuscan city. And there are plenty of excursions departing every day!

On this list, we have included the best tours combining the city of Pisa and Siena, and some Siena wine tours. For those preferring a more personalized experience, you’ll also find a list of private tours.

Image of Piazza del Campo with the Mangia tower seen from above, in Siena

All in all, there are plenty of great Siena tours from Florence to choose from. So, if you’re looking for the best ways to explore the stunning city, keep reading!

Wondering why you should trust me? I’m like your savvy Italian friend who knows all the right places. Born and raised in Bologna, with 10 years of experience helping millions of people plan their Italian trips, I find the best activities and tours like a local finds his favorite espresso bar. No fuss, just the best.

I generally use Viator and Get Your Guide to book tours around the world. I especially recommend them for their great cancellation policy. If your plans change, you can cancel most activities up to 24 hours in advance and get a full refund. 

In a rush? These are the best tours

THE BEST TOURSiena, San Gimignano, Pisa, and Lunch at a Winery
SIENA WITH WINE TASTINGSiena, San Gimignano & Dinner in a Boutique Winery
PRIVATE TOURPrivate Tuscany Tour: Siena, Pisa, and San Gimignano

OUR PICK: The BEST Siena Tour from Florence 

Experience the best of the Tuscan countryside with this Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa, and Lunch at a Winery.

Start your adventure by visiting the medieval city of Siena and its Gothic cathedral. You’ll enter the Duomo, and benefit from your guide’s knowledge as they lead you around the city.

Then, head to the Chianti wine region where you’ll explore a vineyard, olive grove, and wine cellar, delving into the world of wine-making. Next up is the hilltop town of San Gimignano, a UNESCO World Heritage Site.

Wander its charming streets, and try the world-champion gelato at Gelateria della Piazza Dondoli.

Finally, marvel at the architectural masterpiece of Cathedral Square in Pisa, where you’ll find the Leaning Tower. You’ll also visit a local winery for lunch and wine tasting before returning to Florence.

Why this tour? Because it’s the most comprehensive! You’ll be introduced to Siena and its surrounding wonders with a professional guide, visiting the major attractions and learning about them. On top of that, you’ll be treated to a scrumptious tasting of the countryside’s best products, including wine!

Read what the reviews say

Alex was amazing and went out of his way to make sure everything was exceptional. Tour structure was balanced between free time and guided. San Gimignano and the amazing wine farm were the highlight but Pisa and Siena were amazing too – bravo guys you rock!”

Sean_U – Read more reviews

This Florence to Siena day trip includes: Roundtrip transportation, a guide, admission fees, lunch, wine tasting, and free time. ➥ BOOK IT HERE

Pisa & Siena Tour from Florence

Discover the beauty of Tuscany on a 12-hour Day Trip to Pisa, Siena & San Gimignano with Lunch from Florence. Start by visiting the iconic Piazza dei Miracoli, where you’ll find the Leaning Tower and the cathedral of Santa Maria Assunta. 

Afterward, explore the UNESCO-listed medieval town of San Gimignano. It’s renowned for its iconic towers and Vernaccia di San Gimignano wine, and overlooks the vast countryside all around it.

You’ll then get to indulge in local cuisine with a typical Tuscan lunch and wine tasting. Finally, make the most of your free time in Siena after enjoying a guided walking tour of the city. 

This tour includes: Transportation, a guide, lunch, wine tasting, a walking tour of Siena, and entry ticket to Siena’s Duomo. BOOK IT HERE

Tours to Siena with Wine Tasting

▶️ Check out this Tuscany Day Trip from Florence with Chianti, Siena and San Gimignano. You’ll be able to immerse yourself in the Chianti region, known for its wine production, and visit Tuscany’s top locations in a single day.

An expert local guide and driver will take you around Siena’s historic center, telling you all about its history and traditions. 

You’ll then enjoy a gourmet lunch with wine pairings at a Chianti vineyard, and then head to the charming Medieval village of San Gimignano. Discover the town’s unique history and culture on a walking tour, and return to Florence at the end of the day.

Tuscany Day Trip from Florence with Chianti, Siena and San Gimignano

This tour includes: An expert guide, roundtrip transfers, a walking tour of both Siena and San Gimignano, lunch, and wine tasting. ➥ BOOK IT HERE

▶️ Get ready to be bewitched by Tuscan charm with the Medieval Gems of Tuscany: Siena, San Gimignano and Monteriggioni. You’ll discover UNESCO-listed landmarks and sample world-renowned wines on a full-day trip. 

Hop on a coach and enjoy the drive to the first stop, the stunning medieval castle of Monteriggioni. Explore the cobblestone alleyways and hidden gems of this charming town before heading to Siena.

There you’ll join a guide on a walking tour of the city’s picturesque streets, historical landmarks, and stunning Cathedral. 

Next up is San Gimignano, a hilltop town with imposing Medieval towers that remain intact to this day. You’ll cap off the trip with a wine-tasting session at a local winery, paired with regional delicacies. 

This Florence to Siena tour includes: Transportation, a guide, a walking tour of Siena, all tastings, and free time. BOOK IT HERE

▶️ This Small-Group Day Trip to Siena and San Gimignano with Dinner in a Boutique Winery is a great option. You’ll explore the scenic city of Siena and its famous Piazza del Campo, which has been the site of many historic events, with a knowledgeable guide.

Then, head to the medieval hill town of San Gimignano, where you’ll have free time to roam its charming streets.

End the day at a Chianti winery, savoring a delicious 3-course dinner paired with fine local wine. With only 16 people on the tour, you’ll get a personalized experience.

This tour includes: Roundtrip transportation, a guide, a Siena walking tour, and winery visit with tastings and food. ➥ BOOK IT HERE

Private Tours To Siena from Florence

▶️ Escape the crowds with this Private Tuscany Tour: Siena, Pisa, and San Gimignano from Florence. You’ll travel like royalty in a luxury Mercedes, cruising through the picturesque Tuscan countryside on your way to Siena.

There, enjoy free time to wander around the UNESCO-listed historic center, before hopping back in the car to head to San Gimignano. 

The tour’s last stop is Pisa, where you’ll have a photo opportunity at the famous Leaning Tower and other monuments around the Square of Miracles.

This Siena day trip from Florence includes: Hotel pick-up and drop-off, transportation, water, and free time at the three locations. ➥ BOOK IT HERE

▶️ Check out this Private Tuscany Tour from Florence including Siena, San Gimignano, and Chianti Wine Region.

You’ll travel to the Medieval settlements of Siena and San Gimignano, where your guide will show you around. This gives you the opportunity to learn about their unique history and customs. 

Wander through Siena’s historic center and admire the Gothic cathedral and Piazza del Campo. Admire the panoramic views from the hilltop San Gimignano, and then enjoy the drive to the Chianti region.

At a local winery you’ll discover the secrets of wine-making and indulge in a delicious tasting at your own expense.

Explore the scenic countryside, dotted with olive groves and vineyards, with a private driver.  

This Siena day tour from Florence includes: Hotel pick-up and drop-off, a driver/guide, bottled water, and free time at the locations. ➥ BOOK IT HERE

▶️ Visit two of the most picturesque towns in Tuscany on this Private Tour to Siena and San Gimignano with Wine Tasting and Lunch. Immerse in the glory of the countryside as you leave Florence behind on your way to Siena.

There you’ll get to marvel at the stunning cathedral and historic square, where the famous Piazza de Campo is. Then, head to a local farm for a scrumptious lunch paired with different wines.

Your tour continues to San Gimignano, a hilltop town renowned for its 13 Medieval towers and the glorious views it offers. 

This tour includes: Hotel transfers, a driver/guide, free time, and lunch with wine tastings. ➥ BOOK IT HERE

  • Stefania Guglielmi

    Stefania Guglielmi is the founder of Every Steph. Originally from Bologna, Italy, she's been traveling full-time since 2016 and has visited over 50 countries across 6 continents. She believes sustainable travel and luxury travel can go hand in hand and has been advocating for responsible tourism since 2014. Stefania's advice and travel experiences have been featured in important publications such as Business Insider, Refinery29, and Yahoo Money.