Tuscany Walks & Chianti Wines

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Tour Overview

The intoxicating beauty of Tuscany is there for all to see. But that’s just the start on this gentle small-group hiking adventure. Guided by an expert tour leader, we experience the Garden of Italy through the eyes of a local, staying in the small village of Pancole, where we’re treated to classic Italian hospitality by the Sabatini family. Our walks take us through beautiful vineyards and we explore the Renaissance cities of Siena and Florence with expert local guides. Of course, we also sample several varieties of the local chianti together, forging friendships that could last a lifetime.



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Highlights

  • Experience classic Tuscany on foot: rolling vineyards, Renaissance cities and medieval villages

  • Sip chianti and other local wines on three separate tasting experiences

  • See Siena through the eyes of local on a history and culture tour with a local guide

  • Discover magnificent Florence on a walking tour with a local guide

  • Feel like one of the family with a stay in the Tuscan hills at Hotel Le Renaie

Itinerary

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Day 1 : Start in Pancole

Location: San Gimignano

Meals Included: Dinner

Start at Hotel Le Renaie, our welcoming family-run hotel 4mi (6.5km) from San Gimignano. In the evening, our guide will hold a welcome meeting to discuss the week ahead, give advice on the local area and answer any questions.



Please note: on selected dates there may two Exodus groups at Hotel Le Renaie. Our experienced team of leaders will tailor the itinerary and order of listed activities to ensure you enjoy each activity with your own small group. Where a second group is running, private transfers will be used for the additional group.



If you have extra days at hand and are willing to extend your adventure, consider booking additional nights in Pisa or Florence. Speak to your Sales Consultant for more information on our 'Pre-Tour', 'Post-Tour' and 'City Extension' packages.
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Day 2 : Walk a section of the Via Francigena; afternoon local wine tasting

Location: San Gimignano

Meals Included: Breakfast, Dinner

Get ready for a day full of history and nature as we explore one of the most popular sections of the Via Francigena, which links the villages of Gambassi Terme to San Gimignano. The Via Francigena is an ancient pilgrimage route that links Canterbury in the UK to Rome; the full trip takes well over 90 days, but our section is far gentler, cutting through olive groves and vineyards.Later in the afternoon, we head to Azienda Agricola Pietralta, a picturesque farmhouse in the heart of the countryside, where we enjoy three glasses of wine, a trio of cheeses and a tour around the farm.Dinner this evening is back at the hotel, where we have time to relax, perhaps with a game of billiards or another glass of local wine on the garden-view terrace.

Day 3 : Walk in Radda in Chianti

Location: Radda in Chianti

Meals Included: Breakfast

This morning, we enjoy a local history in the heart of the Chianti area, covering the scenic route in a circular walk. We cut through woodlands, where we can admire the emerald vineyard valleys. In the afternoon, you have some free time to wander around and maybe join an optional tasting  of the much-acclaimed chianti classico at one of the many local wineries.

Day 4 : Travel to Siena and explore the stunning historic centre; learn about Tuscan and Italian wines at a wine school

Location: Siena

Meals Included: Breakfast, Dinner

After breakfast, we head to Certaldo station and catch a train to Siena (approximately 45 minutes). This medieval city is dominated by impressive gothic monuments and is divided into 17 contrade (districts), each of which goes head-to-head in the twice-annual Palio, a thunderous horse race around the central square for which the whole city turns out.We join a local guide on a tailor-made tour of the city, stopping at the landmarks, plus captivating sites most tourists normally pass by. Our tour includes a visit to a contrada museum, which is typically closed to the public, and dips into botteghe (small, traditional shops) to sample traditional local sweets.You may also opt to visit the medieval Siena Cathedral.In the afternoon, learn about Tuscan wines during a one-hour lecture at the Tuscan Wine School. Unlike traditional wine tastings, this expert-led experience is more educational, offering in-depth insights into Tuscany’s most important wines.

Day 5 : Free day to visit other Chianti villages or relax by the pool

Location: Chianti

Meals Included: Breakfast

Today is free to rest any tired legs at the poolside. Alternatively, your leader can advise on local chianti wine-tasting tours, cooking classes, e-bike and vespa hire or offer assistance for unguided walks or daytrips.

Day 6 : Discover the magnificent city of Florence

Location: Florence

Meals Included: Breakfast, Dinner

Our destination today is Florence, birthplace of the Italian Renaissance. Most of the greats from the movement lived or passed through here: Leonardo da Vinci, Michelangelo, Sandro Botticelli and more. Learn all about it by joining one of the free local tours, which typically take in the highlights.



Join one of the morning tours and you'll have time to visit the Uffizi, an art gallery housing works by Renaissance masters, including The Birth of Venus by Botticelli and the gruesome Medusa by Caravaggio. If you do wish to visit, we recommend prebooking your ticket online to avoid lengthy queues. An ideal slot time would be around 2pm if you're joining the morning walking tour. Tickets can be purchased at www.uffizi.it/en/tickets.

Day 7 : Walk to picturesque San Gimignano: afternoon wine-tasting

Location: San Gimignano

Meals Included: Breakfast, Dinner

After a transfer to the quaint hamlet of San Donato, we walk through farm grounds following the pathway to Montauto and on up to the medieval town of San Gimignano. The walk is not long and should take approximately three hours. The afternoon is spent exploring this beautiful town, including visits to the Palazzo Comunale, a 13th-century stone palace that's home to the Pinacoteca (Art Gallery) and 177ft (54m) tall medieval Torre Grossa. There’s free time to wander and soak up the atmosphere. Before your farewell dinner, we visit the family-run Cesani estate, which produces some of the finest wines in the region. Here we enjoy an expertly led tasting, sampling our way through three glasses accompanied by bruschetta, extra-virgin olive oil and a selection of Tuscan cheeses and charcuterie.

Day 8 : End in Pancole

Location: Pancole

Meals Included: Breakfast

The trip ends after breakfast. Bid Hotel Le Renaie a fond farewell and begin your return journey home.

What's Included

  • All breakfasts, five dinners, three wine tastings

  • All accommodation

  • All transport and listed activities

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What's Not Included

  • Travel insurance

  • Single accommodation (available on request)

  • Visas or vaccinations

  • Local taxes (approximately €10 per person, see Trip Notes)

  • Pre & Post Package

  • Extension Package

Food

All breakfasts, five dinners and three wine tastings are included.



Breakfast is usually a continental-style buffet.



The five included dinners are taken at Hotel Le Renaie. Four meals consist of three courses, dessert and a glass of wine. On Tuesday evening, when the restaurant is closed to the public, you will be treated to a special pizza feast.



All meals are homemade and prepared using locally sourced ingredients and following traditional Tuscan recipes. For this reason, the menu doesn’t include fish-based options.



Vegetarian, vegan, gluten-free and dairy-free choices are available – please advise us of dietary requirements on booking.

Accommodation

Surrounded by Tuscan hills, Le Renaie occupies a privileged spot in the little village of Pancole, just 4mi (6.5km) from San Gimignano. Here, the Sabatini family has created an intimate, friendly retreat with 25 air-conditioned rooms and plenty of places to mingle.



Under the Italian summer sun, the swimming pool area (which has a separate hot tub) is the perfect place to cool down; alternatively, find a shady spot in the flower-filled gardens to sit, chat or read a book. Come evening, gather in the bar-restaurant for delicious Tuscan cuisine and a glass or two of local wine. It’s a popular stop for Pancole residents, so you know it’s good. There are also games tables to keep the entertainment going or you can take your drinks onto the bar terrace for views over the garden, which is filled with hydrangeas and citrus plants.







Amenities



Swimming pool (usually open May to mid-October)

Restaurant serving traditional Tuscan meals

Bar/cafeteria for light snacks and lunches (open every day)

Games tables



Worth knowing



A limited number of rooms have a balcony (facing the pool or garden) and these are assigned by the hotel

Our hotel is in a quiet area with just a couple of wineries and agriturismos nearby. If you did want to explore, San Gimignano is a short taxi ride away

Pool opening dates are subject to local weather conditions and pool maintenance requirements; cooler months may not be suitable for swimming

Videos

Check out our Q&As

  • What is the maximum group size?

    16

  • Are the local guides on the tour English speaking?

    Yes.

  • Are vaccinations required for this tour?

    There are no specific health risks.

  • Who is Exodus Travels?

    At Exodus Travels, we've been exploring the world for nearly 50 years. From Walking and Trekking, Cultural and Cycling, Responsible Wildlife, to Polar and our new Premium Adventures, we are proud to offer award-winning small group and self-guided tours to 100+ countries worldwide. ...more ...less

  • Do you require a visa for this holiday?

    No visa required for British passport holders. Please note in Italy it is compulsory to carry ID with you at all times.

  • Can you assist with pre or post tour accommodation?

    We are happy to assist with pre and post tour accommodation. Please enquire for detailed information.

  • Is there a supplement for solo travellers?

    If you would like to be paired with a tour member of the same gender, there is no additional charge. A single supplement can be requested if you would like your own room.

  • Are flights included in this tour?

    International flights are not included with this tour.

  • Are children permitted to take part in the tour?

    Minimum 18 years old people can go on this tour.

  • What happens if I need to change my holiday date once I’ve booked?

    If you wish to make any changes to your booking, particularly if you need to alter any flights booked through us, please let us know as soon as possible. There is a booking or flight amendment fee of £40 per change and flight amendments often incur extra airline costs depending on the changes to be made and if the ticket has been issued or not.

  • How long has the tour company been trading?

    Exodus has been trading since 1974

  • What documents will I receive before I travel?

    Your final joining instructions and flight details, if booked with us, will then be sent out 2 to 3 weeks before departure. If you would like a hard copy posted, or if you require these any earlier, please contact the customer operations team. We advise that if you are booking connecting travel before receiving these, please ensure you leave plenty of time.

  • Do you operate a “single share” option and how does it work?

    Travellers are welcome to opt to share a room with a tour member of the same gender for no additional charge. If you'd like your own room, we can request a single supplement so that you will have your own room throughout.

  • Can I join the tour once it has departed?

    You are welcome to meet the group after the tour has departed however there is no reduction in rate for joining a tour after the departure date.

Reviews from travellers on this tour

Beautiful Tuscany

Wonderful week - three lovely walks through the Italian countryside and some delicious wine tasting! The wonderful Hill top towns we walked to and through were beautiful and, Siena and Florence were amazing. However, the latter was very busy, but that I suspect is due to the place. ...more ...less

Chilled week in beautiful Tuscany

Just returned from a really enjoyable trip. Stunning scenery, picturesque hillside towns, delicious food and wine and a great group of travelling companions. Mark our group leader was a lovely guy, whose 'can do' approach, knowledge and personality added to the overall enjoyment. ...more ...less

CHIANTI - WALKING AND WINE

We have ben on several walking holidays with Exodus over the years and this certainly was up there with the best

Fabulous

A fabulous combination of walking the Tuscan countryside, combined with wine tastings and city visits. Alejandro was a brilliant leader. Villa Castalta is a perfectly adequate base for a walking holiday. The meals at the Villa are basic but wholesome. The restaurant used in the village were all different and very good. The best being Il Re Gallo. The 3 main walks are all interesting, each finishing in an interesting town for lunch and gelato! Despite the high temperatures during our week (highs of upper 30s) all the walks were at a a relaxed pace with plenty of stops along the route. ...more ...less

Italy October 2018

The Chianti Walking and Wine Tour was truly incredible. It was a vacation for my personal sensory system....to touch the ground that leads to...….the smell of the crisp Italian forest air, the taste of the locally sourced wine and fresh cheese, to see the vineyards, the cypress trees and the villas and to hear the sound of silence and peace, that can only be found walking the Tuscany Country. The tour was about being aware and in the moment, then taking those memories and sharing them with friends. ...more ...less

Beautiful Tuscany

This eight-day trip to Tuscany took place in the Chianti hills some 2,000 feet above sea level, just outside Castellina. Our base was Villa Casalta, a beautiful converted farmhouse which boasts extensive views in all directions and an unheated swimming pool that provided invigorating dips at the end of the day. There were three lovely walks during the week, ranging from five to seven miles in length, over a variety of terrain, all finishing at local mediaeval villages, such as Greve, Radda and San Gimignano, and there were day trips to Siena and Florence, which were enhanced by excellent local guides. On each of the first three days there were also fascinating wine-tasting sessions at different locations. On our final day we had three hours to explore Pisa before our flight home. ...more ...less

Great trip

Lovely wine and hill walking with excellent town/city tours. All very well organised.

CHIANTI: WALKING & WINE

A very well put together trip.

Chianti: walking and wine

An excellent and relaxing holiday.

First trip with Exodus

We had a thoroughly enjoyable varied trip though the walking was more challenging than we anticipated. The uphill and down dale rocky walking was harder for us as we are both in our 70s and these days we have not done so much of this type of walking. Nevertheless, we had an excellent guide in Liz Proctor who made sure that we paced our walking and with her knowledge of the countryside and terrain through woodland, olive groves and vineyards combined with a good humoured small group of 6 persons made our walking very enjoyable. The wine tasting and classes were very informative and fun. On the city days in Sienna and Florence we had excellent guided walks and an in-depth insight into the culture and history ofthese 2 beautiful cities both of which we have visited twice before. The weather was more chilly than expected and the farmhouse although welcoming was not warm enough in the morning or when we came home each evening.th ...more ...less

Read all 67 reviews

1 Select your preferred date

Saturday - Saturday

Oct 11, 2025 - Oct 18, 2025
$2775 $2359 (USD)

Operator discount: -$416 (USD)

Saturday - Saturday

Oct 18, 2025 - Oct 25, 2025
$2775 $2359 (USD)

Operator discount: -$416 (USD)

Book with Confidence

  • Transfer as credit for future tours

    Exodus Adventure Travels allows you to transfer existing payments to a future tour to avoid cancellation fees if you can't travel and inform exodus adventure travels, 90 days before departure.

  • Low Deposit

    Exodus Adventure Travels requires a minimum deposit of 25% or the full booking value, whichever is less, with the final balance not due until 120 days before departure.

  • Cancellation Policy

    We don't charge a cancellation fee, here is a summary of exodus adventure travels charges.

    Up to 90 days before tour starts: Forfeit 100% of deposit.

    At 89 days before tour starts: Forfeit 50% of booking price.

    At 51 days before tour starts: Forfeit 75% of booking price.

    At 30 days before tour starts: Forfeit 100% of booking price.

Tuscany Walks & Chianti Wines

8 Days Starting in Pancole and ending in Pancole

Visiting: San Gimignano, Radda in Chianti, Siena, Chianti, Florence, Pancole

Tour operator:

Exodus Adventure Travels

Tour code:

TDC

Guide Type:

Fully Guided

Group size:

4 - 16

Physical rating:

Easy & Moderate

Age range:

18-99

Special diets catered:

Please inform Exodus of specific dietary requirements

Tour operated in:

English

Activities:

Wine Tasting

From: $2775 $2359 (USD) Operator discount: -$416 -15%

NB: Prices correct on 16-Apr-2025 but subject to change.

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