Siena is one of the most captivating cities in Tuscany, and if you’re visiting Florence, it’s an easy and worthwhile day trip.
I love wandering through its medieval streets, soaking in the history, and admiring the incredible Gothic architecture—especially the breathtaking Siena Cathedral and the iconic Piazza del Campo, where the famous Palio horse race takes place.
Beyond its landmarks, Siena is a fantastic place to dive into Tuscan culture, whether that means sipping a glass of Chianti, indulging in traditional dishes like pici pasta, or browsing artisan shops for locally made ceramics and leather goods.
Since Siena is just 50 miles (80 km) from Florence, there are plenty of great tours that make the trip seamless.
While tours to just Siena aren’t very common, if you’re looking for a combo trip with Pisa, or a wine-tasting adventure in the countryside, there are plenty of options. If you prefer a more exclusive experience, I’ve also included top-rated private tours.
So, if you’re ready to explore one of Tuscany’s most charming cities, let’s dive into the best Siena tours from Florence!
➥ Wondering why you should trust me? I’m like your savvy Italian friend who knows all the right places. I was born and raised in Bologna, just one hour from Florence, and have 10 years of experience helping millions of people plan their Italian trips. I know which tours are worth your time and money, and which aren’t.
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.
Are you in a rush? These are the best tours:
| THE BEST TOUR | Siena, San Gimignano, Pisa, and Lunch at a Winery |
| SIENA WITH WINE TASTING | Siena, San Gimignano & Dinner in a Boutique Winery |
| PRIVATE TOUR | Private Tuscany Tour: Siena, Pisa, and San Gimignano |
OUR PICK: The BEST Siena Tour from Florence
Experience the best of Tuscany with this Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa, and Lunch at a Winery. This comprehensive tour makes the most of the day by visiting multiple world-famous destinations – starting with Siena.
After meeting with your guide at the Florence train station, you’ll board the bus and drive to the first destination.
Start your adventure by visiting the medieval city of Siena on a guided walking tour. You’ll enter the Duomo, visit Piazza del Campo, the site of the famous Palio horse race, and stroll around the picturesque back streets of Siena. You’ll even see the oldest bank in the world that still exists today.
Then, head to the Chianti wine region where you’ll explore an organic, family-run wine estate where you will delve into the world of wine-making. Here you’ll enjoy an informal wine tasting and a hearty Tuscan lunch with wine, homemade pasta, cured meat, and cheeses. For many past travelers, this is the highlight of the day!
Next up is the hilltop town of San Gimignano, a UNESCO World Heritage Site. You’ll have free time to wander its charming streets, find all the remaining standing medieval towers (what San Gimignano is known for) and try the world-champion gelato at Gelateria della Piazza Dondoli.
Finally, last but not least, marvel at the architectural masterpiece of the Square of Miracles in Pisa, where you’ll find the infamous Leaning Tower of Pisa. You can upgrade your ticket to include a skip-the-line entry to the tower (which I recommend doing because time slots are often sold out in high season). You’ll then drive back to Florence where you’ll be dropped off at the pick-up location.
➤ Why is this the best tour? Because it’s the most comprehensive! You’ll be introduced to Siena with a professional guide, where you will visit the major attractions and learn about them. Pisa and San Gimignano, two other UNESCO sites, are also visited in this full-day tour.
On top of that, you’ll be treated to a scrumptious tasting of the Tuscan countryside’s best products, including wine. After all, there’s a reason why over 15,000 people have left 5-star reviews!
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.
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
