Tuscany Day Trip From Florence With Chianti, Siena and San Gimignano

10 hours

Max 14

592 reviews

Tuscany is an incredible adventure: Stunning scenery, historic hill towns, wonderful food & world-famous wines. Experience it all with a designated driver, tour leader and a guided walk through Siena on this all-inclusive Tuscany tour from Florence. You'll spend the morning in Siena, lunch at a Chianti vineyard and then afternoon in stunning San Gimignano. Then return to Florence for dinner!

Siena town from an overlook The facade of the Siena Cathedral The dome of the Siena Cathedral Siena's cathedral has one of Italy's most impressive interiors Siena's central square The streets of Siena Enjoy lunch in a Chianti winery The views over the Tuscan countryside are always stunning Balsamic vinegar is one of the many products that they make in Tuscany Touring the wine cellars Getting a tour of the grounds at a Chianti vineyard Lunch at a Chianti Vineyard Try local specialties at lunch on our Tuscany from Florence day trip Lunch in Tuscany Lunch in Tuscany One of the inhabitants on the Tuscan farm we visit The view from the bell tower of San Gimignano
  • Sites Visited
  • Siena town
  • Siena Cathedral
  • Chianti farmhouse & vineyard
  • San Gimignano
  • Piazzale Michelangelo (for views over Florence)
  • Tour Includes
  • Expert English-speaking tour leader throughout
  • Guided tour of Siena town including
  • Entrance to Siena Cathedral
  • Lunch & wine-tasting in Chianti
  • Comfortable air-conditioned transport
  • Professional driver (separate to Tour Leader)
  • Small groups of 14 or fewer

Take a walk through Siena, San Gimignano & the Chianti wine region.

Experience the best that Tuscany has to offer on this carefully-planned itinerary, taking you to two of the most beautiful (and historic) towns of the region & an authentic family-run vineyard/farmhouse for lunch. With an experienced driver on hand you don't have to worry about winding roads - or drinking too much of that wonderful Chianti wine!

Your driver and tour leader will pick you up in a private, air-conditioned transport in central Florence (depending on the group size, there might be two vans which the tour leader will shuttle between) and spirit you out into the hills above the city. First stop: Piazzale Michelangelo, a small piazza offering the most jaw-dropping views of Florence. You may not have heard of it yet but you'll recognize it when you see it; this is where most postcard photos are taken from.

Then it's back into your minibus and over the rolling hills of Tuscany to the town of Siena, one of the most beautiful, and historically important in the area (if not the country). Here your leader will guide you through beautiful Medieval streets (their great condition is a rarity in this region, so heavily shelled during WWII), telling you stories from the city's long history, and take you to the enormous central square where the world-famous Palio horse race takes place. Before you leave you'll have a chance to pop into the stunning cathedral (except on Sundays and festivities, when its closed) with pre-reserved tickets. Your guide will stay outside but they will give you an overview of the architecture and tell you what details to look out for once inside.

All this exploring will give you an appetite so after Siena you'll head to a local vineyard for a tour of the cellars, a wine tasting, and a delicious homemade lunch of locally-sourced ingredients. Once upon a time Tuscany's food was considered cucina povera, or poor food, for its reliance on ingredients like tomatoes, bread, and olive oil. Thankfully today we know better. Eat your lunch on the terrace overlooking the rolling hills and vineyards of Chianti. Of course there will be plenty of wine to wash it down with - we highly recommend the red.

Finally, you'll spend the afternoon in the hilltown of San Gimignano. This is one of the best-preserved of the medieval villages, built high atop hills to keep a lookout for hostile armies. Your time here is your own, so feel free to shop for souvenirs, enjoy a coffee in one of the charming piazzas, or climb to the top of the church's belltower for incomparable views of the countryside.

This trip is all about seeing as much of Tuscany as possible without any of the difficult planning and navigation. We'll take care of the logistics so all you have to do is enjoy the food, the scenery and the sightseeing.


592 Verified Reviews

This Walks of Italy tour was incredible!

The guide and driver were extremely friendly and helpful. My sister and I enjoyed the small group in the van and had a great time seeing the beautiful Tuscany!

Great trip with a great group. Really enjoyed the guide, and the driver was nice also.

This was a terrific way to experience smaller towns and the countryside of Tuscany without having to rent a car. The winery visit was very special--the food and wine were excellent. The van was clean, cool, and very comfortable. I'm so glad I chose Walks of Italy to help me fully experience Florence and Tuscany. Every guide was exceptional-friendly, fun, and well-informed. Thank you!


Does this tour include lunch?
Yes! Please email us beforehand and let us know if you have any dietary restrictions or food allergies.
Does this tour accommodate vegetarians & people with food allergies?
Yes, but please contact our customer service team after you book ([email protected]) so that your guide will be aware on the day of the tour. Also, not all of the tastings on the tour can be substituted for others, but we will do our very best to make sure that you always have something to eat.
What if the weather is bad (rain, snow, hail, etc.) on the day of my tour?
Our tours run rain or shine so please dress for the elements. We also ask you to please remember hats and sunscreen if you are taking this tour in the summer as it might be very hot.
Can I bring my child's stroller on this tour?
Although the places we visit on this tour accomodate strollers we don't always have enough room in our transport vans to accomodate them. Please notify us after booking if you are traveling with an infant. Also contact us after booking if you require a car seat.
Can I take this tour if I use a wheelchair?
Unfortunately, our vehicles cannot accomodate wheelchairs and some of the sights, like the farm, farm, are not wheelchair accessible.

The Perfect Guide, Every Time

We take care to assign our guides to the perfect tour for their particular skill set; so you’ll always have the perfect companion for your experience. Here are a few of the guides that regularly lead this tour.

Anna C.


Anna has worked a lot of different jobs in her life, but she only recently became a tour leader. Three years into the job and it is starting to feel like the culmination of her life's experiences.