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Tours/Europe/Italy/Tuscany

Walking in Chianti Tour

Discover the delightful food and drink of Chianti on this self-guided walking tour

4.7 (54 ratings)

Italy, Europe

Happiness Promise

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From $925USDBook Now

Lifetime Deposit - Lifetime deposit means if you need to cancel your booking you’ll get a credit for your full deposit to use on your next booking.

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About this tour:

8 days

Apr-Oct

Walking

Self-guided, Private

Hotels

Moderate (3/5)

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Why travellers choose this tour

At 10Adventures, we take care of the details so that our guests can focus on making memories. Enjoy these key features on this tour.

We're Canadian

Book with a Canadian company whose mission is to help you travel the world.

Meals

Don't worry about meals. 7 breakfasts are included.

Transfers

Check out the 'What's Included' tab for more info on personal transfers during your tour.

Local Support

Travel stress-free knowing in-country local support is available by regular phone or WhatsApp to support you during your tour.

Payments Made Easy

Enjoy the flexibility and ease of staggered payments in your own currency using your choice of credit card.

Route Resources

Route notes, maps, and/or a trail app make navigation on this tour a breeze.

Park Entrance Fees

Included where possible! Check the 'What's Included' tab for more info on park entrance fees during your tour.

Luggage transfers

Take a load off, with optional or included luggage transfers. Check inclusions for further details.

Accommodation for Walking in Chianti Tour

This tour is based in 2- 4-star hotels, but there is an option to book in upgraded hotels if you’d like a more luxurious stay.

The hotels offer pleasant rooms with excellent locations. Rooms are double occupancy, and single travelers will pay a supplement. In some cases, accommodation listed below may need to be substituted for other, comparable accommodations.

Single Rooms and Solo Travelers
Solo travellers must pay a supplement that varies based on the season (please inquire to find out more). However, it’s definitely possible to match single travellers up.

Night 1-2

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Hotel Park Palace in Florence

This hotel offers rooms with TVs, minibars, air conditioning, and free WiFi. The atmosphere is romantic, and the views are pleasant.

Night 3-4

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Albergo del Chianti in Greve

Albergo del Chianti was recently renovated, and rooms offer private bathrooms, TV, and free WiFi. It is centrally located with plenty of great shops nearby.

Night 5-6

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Hotel Palazzo San Niccolo in Radda

This hotel features beautifully painted murals and Tuscan charm around every corner. Enjoy a fitness centre and rooms with flatscreen TVs, free WiFi, and sauna access.

Night 7

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Hotel Chiusarelli in Siena

Hotel Chiusarelli*** is in the city center of Siena and finds its natural setting in a neoclassical villa built around 1870.

Hotels on Standard Tour

Planning a group trip?

Learn how we help group of friends, outdoor clubs and families get the tour they’ve been dreaming about.

Walking in Chianti Tour Details

Overview

Itinerary

Walking in Chianti Tour Itinerary

Day 1

Arrival in Florence

Overnight Location - Hotel in Florence | Distance - None | Meals - None

Arriving in Florence marks the start of your walking tour of Chianti. Breathe in the city air and take some time to explore Florence’s stellar collection of Renaissance buildings and squares. Walk along the flowing Arno River. Stroll to the Piazza della Signoria before finding one of the many excellent restaurants for dinner.

Day 2

Walk to Fiesole

Overnight Location - Hotel in Florence | Distance - 3/6 hours, 8/16km, 224/556m elevation gain | Meals - Breakfast

A quick morning bus ride takes you to Settignano, where you will begin today’s walk. You’ll pass lush cypress forests, olive groves, and have a birds-eye view of Florence. The colorful town of Fiesole is a great chance to see Etruscan ruins, a preserved Roman Amphitheatre, and a Franciscan monastery before the day ends.

Day 3

Choice of walks in Greve in Chianti

Overnight Location - Hotel in Greve | Distance - 2.5 hours, 11.4 km, 425m elevation gain or 3.5 hours, 10 km, 447m elevation gain | Meals - Breakfast

This morning, take a quick transfer to Greve in Chianti, where rustic markets and excellent wine await. Once you’re checked in to your hotel, stop by Le Cantien di Greve for a tasting of over 50 of the region’s fine wines. Then, you have the choice of two routes for today’s walk. The first starts in Greve’s main square, and then leads you through the Chianti Classico region. On this walk, you get wonderful vineyard views and glimpses at the “azende agricole” where the wine is produced. The second option heads into the nearby forest, where you’ll pass through lush wild vegetation, olive groves, and vineyards. Abandoned farms beckon you for a look and beautiful villas dot the trail. You’ll take a moment to appreciate the panoramic view from Montefioralle before heading back to Greve.

Day 4

Pananzo loop walk

Overnight Location - Hotel in Greve | Distance - 4 hours, 11.7 km, 384m elevation gain | Meals - Breakfast

The next leg of your walking tour of Chianti is a loop walk based out of Panzano. The village is surrounded by undulating hills, and the trademark Chianti vineyards and forests surround you.

Day 5

Radda in Chianti

Overnight Location - Hotel in Radda | Distance - 4 hours, 13 km, 506m elevation gain | Meals - Breakfast

A morning transfer takes you up to the topmost Chianti hill, Monte San Michele. Your walk descends through a tree-clad valley of century-old chestnut trees before pausing in Volpaia. Grab lunch and a glass of wine at one of the enotecas before continuing on to Radda in Chianti.

Day 6

Radda in Chianti loop

Overnight Location - Hotel in Radda | Distance - 5 hours, 15.8 km, 586m elevation gain | Meals - Breakfast

Today’s walk is pleasant and relaxing. The warm Tuscan sun warms your shoulders while you tour the old centre of Radda. Then, follow the alleyways to the church of Santa Maria Novella. The roads winds up through vineyards, where you’re welcome to stop for a glass at the excellent local wineries.

Day 7

Siena

Overnight Location - Hotel in Siena | Distance - None | Meals - Breakfast

After breakfast, transfer to Siena. Siena is a stunning city packed to the brim with Renaissance history. Snap a photo in the shell-shaped square where the biannual Palio horse race occurs, or stop by the architectural hotspot of the Duomo. There are medieval palaces and towers everywhere, and they make a perfect backdrop for the day’s exploration. You’re welcome to explore Siena as you please today with no set route, so spend time where you enjoy it best!

Day 8

Departure from Siena

Overnight Location - None | Distance - None | Meals - Breakfast

A final breakfast caps off the Walking in Chianti Tour. You’re welcome to book more nights in Siena if you’re not quite done exploring!

Tour Highlights

What's Included

Dates & Prices

Solo Traveller

Single Room (2+)

Double/Twin Room

Triple Room

Dates	Solo Traveller	Single Room (2+)	Double/Twin Room	Triple Room
Apr 1, 2025 to Apr 11, 2025	$1,950USD	$1,675USD	$1,175USD	$995USD
Apr 12, 2025 to May 25, 2025	$1,950USD	$1,675USD	$1,175USD	$1,025USD
May 26, 2025 to Oct 4, 2025	$1,995USD	$1,750USD	$1,175USD	$1,025USD
Oct 5, 2025 to Oct 18, 2025	$1,950USD	$1,675USD	$1,175USD	$995USD
Oct 19, 2025 to Oct 31, 2025	$1,925USD	$1,650USD	$1,150USD	$975USD

Optional Extras
Printed trip documents:$50USD

Accommodation

Map

Reviews (54)

Tour Booking Process

FAQ

Frequently asked questions for Walking in Chianti Tour

How hard is the Walking in Chianti Tour?

We rate this tour as a 3 / 5. While the distances aren’t that long, the Chianti region is very hilly, and there is moderate elevation gain most days.

Do I need a Visa to travel to Italy?

Check with your local country about visa requirements. You could also try this website, though you should verify with your government.

Are meals included on the Walking in Chianti Tour?

7 breakfasts are included.

Do I need insurance?

Yes. You will need to acquire travel insurance that covers hiking/walking. Get your Travel Insurance.

How do I get to Florence to start this tour?

The best airport to arrive at is Florence (FLR). From FLR, take the direct local bus to downtown.

Is the Walking in Chianti Tour guided?

No, you will be provided with maps, route guides, notes, and 24/7 telephone support to complete your self-guided tour.

Where does the Walking in Chianti Tour end?

The tour ends in Siena, where you can travel from the SITA-TRA.IN bus station to Florence. Check the bus schedule here.

I’ve never been on a self-guided trip! How does it work?

Self-guided travelling is not difficult! For many, it is a preferred type of travel as you are in charge of your own time and pace. You are provided all the information on which direction you need to go daily. You don’t need to carry lots of things with you and can only carry your daypack, as your luggage will be picked up from your hotel daily in the morning and delivered to your destination hotel.

Can I rent any equipment?

No, please come prepared with any walking/hiking equipment desired.

Do I need special vaccines to travel to Italy?

Check with your family doctor.

Are there any travel restrictions for Italy?

Please check with your local government about travel restrictions before you book your tour. This map from the US Department of State provides an overview of the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provide advice on foreign travel. Note that the travel advice may change depending on your nationality.

Tour Difficulty

From $925USD

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Walking in Chianti Tour

Walking in Chianti Tour

Walking in Chianti Tour

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What travellers are saying about 10Adventures

Why travellers choose this tour

We're Canadian