Tuscany Walks & Chianti Wines

Tuscany Walks & Chianti Wines

Aerial view of famous medieval San Gimignano in the province of Siena, Italy
San Gimignano

Aerial view of famous medieval San Gimignano in the province of Siena, Italy

Days 1-2
Siena

The medieval town of Siena, Italy

Day 4
Florence

Florence, Italy

Day 6
Aerial view of famous medieval San Gimignano in the province of Siena, Italy
San Gimignano

Aerial view of famous medieval San Gimignano in the province of Siena, Italy

Day 7

Map
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8 Days From

$2775

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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. ...more ...less

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

Places You'll See

Siena, Italy

The Uffizi Gallery In Florence, Italy

Aerial View Of Ponte Vecchio Bridge, Florence, Italy

Itinerary

Expand All

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 an eco-friendly wine estate near Certaldo where your discovery of Tuscan wines will be taken to the next level with a sensory and aroma experience, accompanied by mouth-watering traditional appetisers.



Dinner this evening is back at the hotel, where we have time to relax a little more, 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

  • Tour leader throughout

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.
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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
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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

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

Tuscany Walking and Wine

A really enjoyable and varied week in Tuscany. Three lovely walks through forests and vineyards. Stunning hilltop villages and market towns. Excellent wine tastings and winery visits, each a little different, and we certainly drank a lot of local Chianti. Liz, our guide, was efficient, knowledgeable, capable and so friendly. We had plenty of time to explore the cities of Siena and Florence at our own pace, and on our free day most of us opted for a cookery class at a local restaurant. Enormous fun and the lunch we helped produce, was amazing. The family run farmhouse where we stayed was full of character, and they made us so welcome. The evening meals were generous and based on local produce and served with their own estate wines. ...more ...less

Tuscany Walks & Chianti Wines

A wonderful trip with a great group leader who went above and beyond to make sure we were all comfortable and well taken care of.

1st time Exodus experience

This was our first holiday with Exodus. Usually we are independent travellers so we were both a bit nervous about a group 'organised ' trip but we needn't have worried. We had a great group of people; different backgrounds and nationalities which made for an interesting week of getting to know each other. Our fabulous guide Mark was absolutely brilliant, patient, helpful and very accommodating, keeping us out of too much sun, well watered and well informed about the various places we visited. Roberta, our host at the villa was absolutely lovely and looked after us wonderfully with the help of Margarita. We really had a great week and as well as being very impressed with our trip we've also been inspired by the experiences of Exodus from our fellow travelers; definitely food for thought for future trips. ...more ...less

A fabulous week in Tuscany

The week was full of many different experiences. Despite a smaller group than usual, the walking was excellent, even though it was very hot. The wine-tastings were very different, and all informative, some with some nice nibbles included. The hotel is lovely with an excellent (ask for a room with a view) with a swimming pool and home made pizzas to die for. City-wise, we visited St Gimignano, Siena (brilliant guided tour included) and Florence. Our guide, Jordan, did a great job keeping us under control. ...more ...less

Perfect Holiday

Great holiday with a fantastic leader. A good starter walking holiday for us, with the right balance of walking and sight seeing providing an excellent introduction to Tuscany.

Chianti Walking and Wine Tour

This tour was fantastic! Staying at Casalta was excellent. It is located close to the township and the food and people were awesome. It was an excellent balance of walking, wine, and socialising with the group.

One of the best...

For me, there are three criteria that make a great Exodus trip: the members of the group, the leader, and the location/activities. The members of the group on this trip were wonderful: great company, entertaining, and considerate. Mark was the perfect leader (see below). The location was stunning with beautiful Tuscan villages, towns and cities. How can the combination of wine and walking be beaten? (OK, maybe cycling and wine at a push...) ...more ...less

Chianti June 2014

This was our first Exodus trip, it was well organised, everything was as per the trip notes & I would certainly look at other Exodus holidays.

Our first Exodus trip

This trip met all our expectations and requirements and was a really good holiday for us. The daily organisation and all the experiences were excellent, we cannot praise Liz enough for her competence at making the week so good. The walks were amazing, just at the right level for us and we felt spot on with the leisurely/moderate rating. The hotel was beautifully situated, traditionally furnished, clean and homely, the staff were very nice, helpful and pleasant. Just a few quibbles that have prevented us awarding the top rating: the hotel breakfast was good, although a bit more variety would have been nice, but the evening meals taken in the hotel were fairly basic. The meals taken outside in local restaurants were fantastic. Our pre trip information supplied from Exodus gave us the wrong departure terminal at Heathrow, which we realised just two days before departure, however, this was dealt with efficiently and we appreciated how well it was handled. All in all an excellent week, we enjoyed it immensely and are looking at our next adventure! ...more ...less

Read all 67 reviews

1 Select your preferred date

Saturday - Saturday

Jun 14, 2025 - Jun 21, 2025
$2775 (USD)

Book with Confidence

  • Transfer as credit to 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, 43 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 90 days before departure.

  • Cancellation Policy

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

    Up to 70 days before tour starts: Forfeit 100% of deposit.

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 (USD)

NB: Prices correct on 28-Feb-2025 but subject to change.