Tuscany Wine Tour from Florence to Siena & Chianti

Enjoy a luxury Tuscany day trip to visit Siena and San Gimignano then taste food and wine in Chianti

Travel Flexibly 4.9 / 5 See All 103 Reviews · 9.00h · Florence, Italy

Looking for a simple way to explore Tuscany from Florence? Want to visit an iconic winery in Chianti and take in those epic views in San Gimignano? Then you've found the perfect tour! Sit back and relax on this small group food and wine adventure through the Tuscan countryside. You'll see the farms, wineries, and vineyards that make the region’s cuisine so famous. Learn the secrets of Chianti wine and watch local life unfold in tiny medieval villages that have barely changed in centuries.

  • A memorable day in the countryside
  • Luxury transportation from Florence
  • Rolling hills of Tuscany
  • Historic Siena
  • Siena Cathedral
  • Explore the Chianti region
  • Traditional farm and winery
  • Tuscan cuisine for lunch
  • San Gimignano
  • Transportation back to Florence

Meet your trip leader in Florence at Viale Filippo Strozzi 1, and hop aboard your luxury, climate-controlled vehicle with no more than 15 other travelers. You'll enjoy an entertaining ride from Florence through the most famous food and wine region in Italy, accompanied by a passionate local trip leader and private driver. Tuscany awaits to share its bounty of gorgeous foods and wines, and you'll meet the local people who can show you wine-making techniques passed down through generations. You'll also get to explore the insanely beautiful old towns of San Gimignano and Siena, and enjoy a hearty, delicious lunch in Chianti.

Tuscany Wine and Food Tour Description

Your 9-hour day trip from Florence includes:

  • Round-trip transportation from Florence in a climate-controlled vehicle

  • Visit beautiful Siena with free time to visit the cathedral (on your own)

  • Wine tour and tasting at a traditional, family-run winery in Chianti

  • Traditional Tuscan lunch

  • Visit the picturesque medieval town of San Gimignano

  • An English-speaking trip leader for the day

  • Maximum group size of 16

Historic Siena

Your first stop on this Tuscany day trip is the famous city of Siena. Twice a year, the city holds the famous Palio horse race that has been run since the Middle Ages in Siena's central square, Piazza del Campo. Along with your knowledgeable trip leader, you'll see this famous square and the oldest bank in the world. After getting oriented in Siena, you'll have some free time to explore, and we recommend purchasing a ticket to visit the Siena Cathedral on your own.

Chianti Winery for Lunch and Wine Tasting

Continue your journey through the Chianti hills and olive groves, before arriving at a traditional family-run farm and winery. You'll learn from the locals about famous grapes and the winemaking process from vine to bottle, before sampling them yourself!

Then sit down for a delicious lunch made from locally grown ingredients from the farm, staying true to the Italian slow food movement and traditions of Tuscan cuisine. Lunch and wine are included, and it's easy to order a few extra bottles to take home with you too!

Medieval San Gimignano

The next stop on your Tuscan journey is an incredible little town, sometimes nicknamed “Medieval Manhattan.” As a UNESCO World Heritage site that feels straight out of a fairy tale, San Gimignano is known for the towers that create its iconic skyline, bringing to mind modern day skyscrapers. Once inside the city walls, enjoy some free time to explore this remarkable and historic town. 

Chianti Region to Florence

After an idyllic day visiting historic Tuscany cities and enjoying the food and wine of Chianti, it's time to head back to Florence. Simply sit back and relax as your professional driver takes you safely back to the city.

What you get with this tour
Round-trip transportation from Florence in a climate-controlled vehicle
Visit beautiful Siena with free time to visit the cathedral (on your own)
Wine tour and tasting at a traditional, family-run winery in Chianti
Traditional Tuscan lunch
Visit the picturesque medieval town of San Gimignano
An English-speaking trip leader for the day
Maximum group size of 16
Tripadvisor Logo

See what people are saying

103 total reviews

Leave a review
4.9/5 (based on 103 reviews)
5 stars
4 stars
3 stars
2 stars
1 stars
Fun Day
17 November 2023
D
Reviewed by
Dara Fraser

Just the right balance of support and independence- happy with our choice! Meeting point easy and driver and guide ( I think Gianni & Sara) went above and beyond to give us an extra surprise at the end. Impressed tour went ahead in very nice van for just four visitors. Great value and very ethical policy.

22 October 2023
S
Reviewed by
Sarah williams

Was a good day out. Would prefer longer at San Gimignano than Siena. Lunch was amazing was lovely to sit and chat with everyone on our group. TBH I'm not sure why we had 2 tour guides and tbh I'm not sure why we had them at all, as they didn't give alot of information and we had free time in the 2 towns anyway. Overall was good, but not great compared to other tours we have just done.

Excellent way to see Siena & San Gimignano
16 October 2023
R
Reviewed by
Rosalind Odin

We had a really great time on this tour . There were 15 of us total and they divided us into two vans. Very comfortable and it was cool getting to know the other people on the tour. The tour guide, Manny, was s lovely Italian woman who spoke really good English. Unfortunately, she could only be in one of the vans at a time but she switched the one she ride in during the day. She was great at explaining history and the sites to see. I liked that they drove you to Siena and San Gimignan,, but let you explore on your own for a couple of hours. In the middle of the day, between towns , we went to a family owned winery that makes excellent Chianti and it was reasonable to buy their wine and ship bottles home, which is not typically . . They served us a very nice lunch there as well. All in all a really good day and I would really recommend this tour.

show more reviews

Frequently Asked Questions

What to bring?

Bring sunscreen in the summertime and a bottle of water. You'll also want comfortable walking shoes to wander the towns and vineyards.

I'd prefer a private day trip to Chianti. Can this be arranged?

Yes, we offer a similar private day trip from Florence with private transportation and pickup/drop-off at your Florence accommodation. Check out our Wine Day in the Chianti Hills From Florence

Is this a private day trip?

No, this is a small-group tour so you'll enjoy the day with just 15 or fewer passengers.

Is a guide included on this day trip?

No, you'll be accompanied by a friendly and knowledgeable trip leader and a driver the entire day, but at most stops you'll be free to explore by yourself after getting oriented at each stop.

Are lunch and wine included in the price of this day trip?

Yes, it's all included in the tour price.

What if I want to see Chianti and San Gimignano but I don't drink alcohol?

If you're not interested in a wine-focused day trip from Florence, feel free to contact us so we can make alternate plans for your travel to the countryside.

What to bring?

Bring sunscreen in the summertime and a bottle of water. You'll also want comfortable walking shoes to wander the towns and vineyards.

Start From: $163.80

available days discounted days

Free 24-hr cancellation on group tours! Learn more

Reserve Now $163.80 / per person
$163.80 / per person
You may also like
Skip the Line
Up to 20% off

Skip the Line

Florence in a Day Combo Tour with David and Uffizi

Explore Accademia Gallery, Ponte Vecchio, Florence Duomo, Uffizi Gallery, and so much more

Skip the Line
Up to 15% off

Skip the Line

Statue of David Evening Tour

See Michelangelo's David on a later tour of the Accademia Gallery with fewer crowds

Skip the Line
Up to 20% off

Skip the Line

Florence Walking Tour with Statue of David

Uncover the best of Florence at the Duomo and Ponte Vecchio, and skip the line at Accademia

Skip the Line
Up to 20% off

Skip the Line

Skip the Line Uffizi Gallery Tour

See Botticelli, Caravaggio, and Michelangelo's masterpieces in Florence's famous Uffizi Gallery

Skip the Line

Skip the Line

Uffizi Private Tour in Florence

Skip the line to see Birth of Venus, Medusa, Doni Tondo, and more with your own private art guide

Private Tour

Private Tour

Livorno Shore Excursion: Florence & Pisa

Maximize your day ashore on this jam-packed private tour with Leaning Tower, David, and more!

Skip the Line

Skip the Line

Complete Florence Duomo Tour with Dome Climb

View this charming city from the terraces of Brunelleschi’s famous dome after touring the cathedral

Guided Tour
Up to 15% off

Guided Tour

Florence Local Food Tour in Santo Spirito

Get an authentic taste of Florence’s exquisite food and wine in a lively local neighborhood

New Tour

New Tour

Early Morning Duomo Tour with Exclusive Entry and Brunelleschi's Dome

Be among the first of the day to enter Florence cathedral on this VIP experience

New Tour

New Tour

Tuscany in a Day Tour from Florence

Visit Siena, dine at a Chianti vineyard, explore San Gimignano, and see the Leaning Tower of Pisa!

New Tour

New Tour

Cinque Terre Day Trip from Florence with Boat Ride

Visit these iconic fishing villages the easy way on this tour to the beautiful Italian Riviera

New Tour

New Tour

Pisa and Lucca Day Trip from Florence

Book a stress-free trip to see the Leaning Tower of Pisa and Lucca's medieval walls in a day

New Tour

New Tour

Skip the Line Duomo Terraces Tour with Dome Climb

Admire the Florence Cathedral, climb to the top of Brunelleschi’s Dome, and enjoy breathtaking views

New Tour

New Tour

Tuscany Day Trip from Rome with Vineyard Lunch and Wine Tasting

Wander through the medieval towns of Montepulciano and Pienza and enjoy a 3-course meal!

Skip the Line

Skip the Line

Florence Private Walking Tour with Michelangelo's David

Explore the famous sites of Florence, with Ponte Vecchio, Duomo, and skip-the-line Accademia entry

New Tour

New Tour

Florence Accademia Gallery Express Guided Tour

Skip the line, marvel at renowned masterpieces and see Michelangelo’s iconic David statue!

New Tour

New Tour

Tuscany Wine Tour by Vespa from Florence

Taste the food and wine of Chianti as you ride through the Tuscan countryside on a vintage scooter

New Tour

New Tour

Pizza and Gelato Making Cooking Class in Florence

Create the authentic food of Italy with an expert pizzaiolo chef, homemade lunch, and wine

New Tour

New Tour

Tuscan Countryside Vespa Tour from Florence

Cruise to the rolling hills of Tuscany and taste local food and wine!

New tour

New tour

Pisa and The Leaning Tower Half Day Tour from Florence

Explore the City famous for its Piazza dei Miracoli and enjoy skip-the-line access with this tour

New Tour

New Tour

Oltrarno Local Food Tour in Florence

Take a break from the crowds and eat like a local in the lively neighborhood of Oltrarno

New Tour

New Tour

Pizza and Gelato Cooking Class in a Tuscany Farmhouse in Florence

Pick fresh ingredients and learn to make authentic, Italian cuisine on an unforgettable day trip!

New Tour

New Tour

Cinque Terre Hiking Tour from La Spezia

Walk clifftop trails to discover vineyards, epic views, and famous villages on Italy's magical coast

New Tour

New Tour

Cinque Terre Tour with Locally Produced Limoncino Tasting from La Spezia

Explore the Beaches and Picturesque Peaks in a Small Group

New Tour

New Tour

Authentic Tuscan Cooking Class in Florence with San Lorenzo Market

Create delicious pasta, tiramisu, and more with market-fresh ingredients and an expert local chef

New Tour

New Tour

Semi-Private Cinque Terre Day Trip & Vineyard Tour from Florence

Discover the best of Cinque Terre with seafood lunch, wine tasting, and transportation included

New Tour

New Tour

Florentine Gondola Boat Tour

Sip wine on the Arno River and cruise by Ponte Vecchio, Uffizi, and more on a classic Barchetto boat

New Tour

New Tour

Florence in a Half Day by Bike Tour

Take a ride through the city's hidden gems from Ponte Vecchio to the Oltrarno neighborhood

New Tour

New Tour

Tuscany Wineland Safari from Florence

Get off the beaten track to explore vineyards, castles, food, and Chianti wine on this 4x4 day tour

New Tour

New Tour

Tuscany Wine Making Experience and Gourmet Dinner from Florence

Dine like Tuscan royalty and create your own Chianti wine blend on this small group VIP evening tour

Skip the Line

Skip the Line

Kid-Friendly Private Florence Walking Tour: David & Gelato

Bring the fun to Florence on this family walking tour that includes a merry-go-round and papermaking

Private Tour

Private Tour

Private Wine Day in the Chianti Hills from Florence

Enjoy an intimate day trip tasting wine and organic food from local farms and vineyards in Tuscany

Private Tour

Private Tour

Private Pisa Day Trip from Florence with Lunch in Vinci

Discover Tuscany on this VIP private tour, with Leaning Tower of Pisa, Da Vinci Museum, and more!

Private Tour

Private Tour

Orvieto, Civita di Bagnoregio & Winery Private Day Trip from Rome

Escape the city on a memorable journey through Umbria’s historic towns to taste fine local wines

Skip the Line

Skip the Line

Private Siena Walking Tour

Explore this charming Tuscan city with an engaging local guide to see the Duomo, San Domenico & more

Private Tour

Private Tour

Tuscany Shore Excursion: Chianti Wine Country and San Gimignano

A Chianti Wine Tasting Excursion

Private Tour

Private Tour

Brunello di Montalcino Helicopter Tour from Rome or Florence

Take to the skies on the ultimate VIP Tuscany tour that includes wine tasting and a gourmet lunch

New Tour

New Tour

San Lorenzo Market Tour and Wine Tasting in Florence

Eat your way through Florence’s historic market, enjoy a wine tasting, and try real Italian gelato!

New Tour

New Tour

Chianti Vineyards Tour and Wine Tastings from Florence

See two luxurious wine estates, taste local wine, and sample delicious produce on this half day tour

New Tour
Up to 10% off

New Tour

Tuscany Winery Tour and Gourmet Bites in Montalcino

Pair irresistible wine with delicious gourmet bites after strolling through picturesque vineyards

New Tour
Up to 10% off

New Tour

Brunello di Montalcino Winery Tour & Tasting

Sip wine and stroll through vineyards alongside an expert guide in the hills of Montalcino

New Tour

New Tour

Vintage FIAT 500 Self-Drive Tuscany Tour from Florence

Get behind the wheel of an iconic Italian car, cruising to the Tuscan countryside

New Tour
Up to 20% off

New Tour

Private Vintage FIAT 500 Chianti Tour with Driver from Florence

Cruise through the hills of Tuscany in style and dine at a Tuscan villa on this exclusive experience

Val d’Orcia Day Trip with Two Wine Tastings from Florence

Val d’Orcia Day Trip with Two Wine Tastings from Florence

Sip on Brunello in Montalcino, wander through Pienza, and savor pecorino cheese in Montelpuciano

New Tour
Up to 20% off

New Tour

E-Bike Tour Through Florence and Tuscan Countryside

Ride along Tuscany’s majestic rolling hills, visit a medieval village, and sample local delicacies!