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 to enjoy the most perfect day trip. 

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 attractions include the famous Piazza del Campo and the Gothic-style Siena Cathedral. There are also plenty of great restaurants, cafés, and shops to discover. You can sample the region’s delicious cuisine and shop for locally-made products. In a nutshell, you can’t get bored in Siena.

If based in Florence, several tours can help you discover the best of Siena and its surrounding countryside. Apart from our top pick, 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 private tours.

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 of Siena, 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 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, which allows you to cancel most activities up to 24 hours in advance and get a full refund. 

OUR PICK: The BEST Siena Tour from Florence 

Experience the best of the Tuscan countryside in just one day with this captivating 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. Then, head to the Chianti wine region to explore a vineyard, olive grove, and wine cellar, before wandering through the charming streets of San Gimignano, a UNESCO World Heritage Site. 

Remember to try the best gelato in the world at Gelateria della Piazza Dondoli! Finally, marvel at the architectural masterpiece of Cathedral Square, where the famous Leaning Tower of Pisa lives. You’ll also visit a local winery for lunch and wine tasting. 

📝 This Florence to Siena day trip includes: Roundtrip transportation, a guide, admission fee for Siena’s Duomo, a guided tour of Siena, lunch, wine tasting, and free time. ➥ BOOK IT HERE

Pisa & Siena Tour from Florence

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

Afterward, explore the UNESCO-listed medieval town of San Gimignano, renowned for its iconic towers and Vernaccia di San Gimignano wine. Indulge in local cuisine with a typical Tuscan lunch and wine tasting and 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, walking tour of Siena, and entrance to Siena’s Cathedral. ➥ BOOK IT HERE

The Best Siena & Wine Tours from Florence

▶️This Tuscany Day Trip from Florence with Chianti, Siena and San Gimignano enables you to enjoy a memorable excursion to the Chianti region, Siena, and San Gimignano. You’ll be accompanied by an expert local guide and driver, who will guide 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, which you’ll explore with a comprehensive walking tour. Wander at your leisure for some time and discover the town’s unique history and culture before returning to Florence.

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

▶️ Get ready to step back in time and be bewitched by the medieval charm of Tuscany with this Siena, San Gimignano, Monteriggioni, and Chianti Wine Tasting Tour from Florence. 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 and then head to Siena. There you’ll join a professional guide on a walking tour of the city’s picturesque streets, historical landmarks, and stunning Cathedral. 

Next, visit San Gimignano and marvel at the fascinating Medieval towers that remain intact to this day. You’ll also get to enjoy a wine-tasting session at a local winery and relish other regional delicacies. 

📝 This Florence to Siena tour includes: Transportation, a guide, a walking tour of Siena, tastings of wine, olive oil and local products, and free time in Monteriggioni and San Gimignano. ➥ BOOK IT HERE

▶️ On this Small-Group Day Trip to Siena and San Gimignano with Dinner in a Boutique Winery, explore the scenic city of Siena and its famous Piazza del Campo, which has been the site of many historic events, accompanied by a knowledgeable guide.

You’ll then head to the medieval hill town of San Gimignano, where you’ll have some 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 as you soak up the sunset. With only 16 people on the tour, you’ll get a personalized and intimate 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 a very special Private Tour of Siena, Pisa, and San Gimignano from Florence. You’ll travel like royalty in a luxury Mercedes, cruising through the picturesque Tuscan countryside as you make your way to Siena. There you’ll enjoy free time to wander around the UNESCO-listed historic center, before hopping back in the car and heading to San Gimignano. 

Marvel at its famous 13 towers and indulge in Vernaccia wine, and finish your tour with a photo opportunity at the famous Leaning Tower of Pisa. 

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

▶️ Discover the wonders of Siena and its surrounding towns on this fantastic Private Tuscany Tour from Florence including Siena, San Gimignano, and Chianti Wine Region. Your personal guide will take you through the Medieval settlements of Siena and San Gimignano, giving you the opportunity of learning about their history and customs. 

Wander through Siena’s historic center and admire the Gothic cathedral and Piazza del Campo, check out 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.

You’ll have a private driver from Florence to Siena and back who will ensure you enjoy a personalized experience as you explore the scenic countryside, dotted with olive groves and vineyards. 

📝 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 VIP Exclusive 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, and 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 pick-up and drop-off, a driver/guide, free time in both Siena and San Gimignano, winery visit, and lunch with wine tastings. ➥ BOOK IT HERE

Siena Tours from Florence FAQs