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

607 reviews

10 hours

Max 14

Why take this tour?

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!

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 Fl...

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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.

  • 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
The facade of the Siena Cathedral
The dome of the Siena Cathedral
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Latest Reviews

Greta was the perfect guide for our day, she is very knowledgeable and a asset to your company. the day was well planned , the lunch was very enjoyable with Greta and our other tour members. we wouldn't hesitate to recommend Walks of Italy to our friends.


FAQ

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.
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.
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.
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 (info@walksofitaly.com) 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.