Chianti: Day Trips and Tours from Siena

Standing out in stunningly beautiful Tuscany seems like a tall order, but that’s exactly what Chianti achieves — with the region’s natural splendor matched and even surpassed by the quality of the products that come from these picture-perfect rolling hills.

That’s why Chianti day trips from Siena remain one of the best things to do in all of Tuscany. Chianti’s countryside offers a wealth of activities, with nature, food, wine and unforgettable architecture on offer.

Whether you want to while your day away during a wine-tasting, explore the Tuscan hills on a scooter or meander through a medieval fairytale — Chianti offers all this and more, ensuring that your day under the Tuscan sun will be one to remember.

Here's all you need to know about Chianti, one of the most unforgettable day trips from Siena.

How to get to Chianti from Siena?

Chianti is a region in Tuscany, located almost exactly in the middle between Florence and Siena.

From Siena to Chianti by car

Renting a car for your travels through Tuscany isn’t a bad idea, especially if you don’t mind the documentation and logistics that come with it. From Siena’s city center, you should head north, following the SR2 route.

Once you arrive in north Siena, you should take the SR222, heading northeast towards the Tuscan countryside and the region known as Chianti. The entire route is around 30 kilometers and will take roughly 1 hour to complete.

From Siena to Chianti by public transport

If you want to use public transport to explore the Chianti region, the world is your oyster — or should that be ostrica? Leaving central Siena, take the number 130 bus and stay on it until you reach the sleepy town of Castellina in Chianti.

The entire journey will take 1.5 hours to complete, but at least you’ll travel through some of the world’s most beautiful scenery.

Guided tour to Chianti from Siena

A guided tour is a wonderful option to explore Chianti as most of your logistical challenges will be taken care of for you. You also have the added advantage of a knowledgeable guide to share vital local knowledge with you.

What is the typical itinerary?

The type of Siena to Chianti day trip you go for will largely influence the tour's itinerary. This is because Chianti refers to an entire region, rather than just one town — meaning the experiences are as varied and excellent as the product that Chianti is famous for.

Typically, a Chianti day trip from Siena will start with a hotel transfer in an air-conditioned vehicle. Next, you’ll head out into Chianti’s breathtaking countryside, which is a treat in itself. The type of day trip you choose will determine your next stop, with wine tastings heading to vineyards and cooking classes going to a Tuscan farm.

Scooter and Segway tours generally visit a collection of hilltop villages and hamlets, taking advantage of the nimble vehicles’ ability to go where cars can’t. Some tours might make a stop in the jawdroppingly beautiful towns of San Gimignano or Monteriggioni where you’ll enjoy a walking tour.

At this point, you’ll usually get to enjoy a traditional Tuscan lunch, if that option is included in your tour. If not, you’ll have the opportunity to visit one of the many exquisite local restaurants before heading back to Siena.

What kinds of tours are available to go to Siena?

Day trips from Siena to Chianti cover a broad base of experiences and destinations, ensuring that no two are the same — and making it easy for travelers to find an expedition that best tickles their fancy.

Chianti Vespa tour from Siena

Roaring Vespas, rolling cypress-studded hills, stunning Tuscan villages and exquisite local produce — this day trip represents the epitome of all that Chianti is about.

Follow your guide as you zip through the scenic countryside in a brilliant scooter tour that will leave you craving more. The highlight of the tour is a delicious antipasto lunch with wine tasting in the middle of a Tuscan vineyard.

A day trip from Siena to Chianti with a cooking class

During this half-day trip from Siena to Chianti, you’ll head into the Tuscan countryside visiting a host of hilltop villages — each more beautiful than the last.

The end destination, however, is a farm in Chianti’s countryside where you’ll experience exactly what Tuscan cuisine is famous for — heartwarming hospitality and fresh, quality products. Following the guidance of your chef and instructor, you’ll learn how to work these simple ingredients to create magical dishes.

Siena to Chianti day trip with visits to San Gimignano, Monteriggioni and wine tasting

Chianti is widely regarded as one of Italy’s most influential wine regions, with centuries-old wineries scattered along these iconic hills.

This day trip aims to take advantage of this reputation, visiting two of the region’s most beautiful towns in San Gimignano and Monteriggioni. After you’ve explored these breathtaking towns, you’ll head to a local vineyard where you’ll enjoy an in-depth wine tasting, led by a sommelier.

Siena to Chianti sunset trip with San Gimignano night tour

While the Chianti countryside is truly a sight to behold during the day, some sights really come to life once the sun sets. This half-day trip from Siena is perfect to experience this otherworldly setting as you’ll drive through the Tuscan hills, bathed in the sun’s fading light.

The main destination is San Gimignano, transformed into a shimmering hilltop city comes nighttime, with spiraling towers gloriously lit up — creating an unforgettable wonderland that will stay with you for ages.

How much does a day trip to Chianti from Siena cost?

Day trips from Siena to Chianti involve a fair bit of traveling, meaning that these tours are seldom cheap.

A Siena to Chianti day trip with visits to San Gimignano, Monteriggioni and wine tasting will cost €70 per person. This makes it one of the most affordable tour options, surprising when you consider all the locations visited.

A Chianti Vespa tour from Siena costs €130 per person, a fair price when you consider that it includes lunch and a wine tasting — as well as an entire day in the Tuscan countryside.

A day trip from Siena to Chianti with a cooking class will also cost €130 per person, and it includes a lunch that you prepare yourself.

A Siena to Chianti sunset trip with a San Gimignano night tour will cost €160 per person. This might seem a bit stiff, but it offers an experience that no other tour comes close to — exploring the mesmerizing town of San Gimignano at night.

What will you see and do?

Chianti

Chianti is sometimes called Italy’s pantry, with some of the best wine, olive oil, beef and cheeses being produced here. But Chianti also offers a feast for the eyes with some of the most beautiful scenery and hilltop hamlets on display — delighting visitors from all over the globe.

Tuscany

Tuscany needs absolutely no introduction as the very word has become synonymous with rolling hills and stunning hilltop villas. The fresh produce available in this area has shaped much of Italian cuisine — and it’s an unmissable area when trying to understand this ancient country’s legacy and history.

San Gimignano

When it comes to hilltop villages, they are seldom as jaw-droppingly beautiful as San Gimignano. Ten towers rise from an already beautiful Tuscan village to create something that verges on the unbelievable and makes superlatives seem to fall short.

When is the best time to visit Chianti?

You can visit Chianti year round, but the best time to visit depends on your preferences. Late spring (April to June) offers pleasant weather and blooming landscapes, ideal for outdoor activities and winery tours. Summer (July and August) is high season with hot weather and larger crowds.

Early autumn (September and October), during the wine harvest season and local wine festivals, is often considered the ideal time, especially for wine enthusiasts. Winter (November to March) provides a quieter, cooler experience, with wineries still open for tours.

Are there any tours to Chianti from other cities in Italy?

Yes, there are tours departing from other cities in Italy:

• Day Trips to Chianti from Florence
• Day Trips to Chianti from Livorno
• Day Trips to Chianti from Pisa
• Day Trips to Chianti from Lucca
• Day Trips to Chianti from San Gimignano

Travel tips

• Try the local cuisine. Don't miss out on traditional Tuscan food like pappa al pomodoro, ribollita, or bistecca alla fiorentina.
• Try local desserts. Cantucci biscuits and vin santo dessert wine are a must.
• Pack a picnic. Buy some local bread, cheese, and wine, and find a scenic spot for a picnic.