Tuscany Walks & Chianti Wines

8 days
Save this trip to your favorites or other list
Additional images not provided by operator
4.7/5 Excellent
100+ reviews  
Save this trip to your favorites or other list

Health Safety +


Cancellation Policy
Small Group Tour
With Renaissance cities, medieval villages and cypress-lined avenues winding through vineyards, southern Tuscany is the perfect place for a relaxing guided walking holiday. Based at the welcoming family-run Hotel Le Renaie, we visit beautiful San Gimignano, Radda in Chianti, the Unesco World Heritage site of Siena and the magnificent city of Florence. During ...
See departure dates


Trip type
Small Group Tour
Lodging level
Standard - 3 star
Physical level
Trip pace
Full schedule


    • Walk the classic rolling hills of Tuscany
    • Stay in a family run 3* hotel
    • Enjoy fabulous chianti wines
    • Visit Siena and Florence

What's this trip about?

    With Renaissance cities, medieval villages and cypress-lined avenues winding through vineyards, southern Tuscany is the perfect place for a relaxing guided walking holiday. Based at the welcoming family-run Hotel Le Renaie, we visit beautiful San Gimignano, Radda in Chianti, the Unesco World Heritage site of Siena and the magnificent city of Florence. During the week, we sample several varieties of the local chianti and learn more about Italian wine on an interactive course at a wine school. Interested in extending  your adventure? Whether you are looking to ease into your destination at a more leisurely pace or to allow extra time to unwind, consider booking additional nights in Pisa or Florence: Pre-tour package Post-tour package City extension package Visit the Trip Notes and speak to your sales representative for more details on the packages, including costs, availability, additional activities, and any special arrangements that can be made. All options are subject to availability. Join us to celebrate Exodus’ 50th anniversary! The departure starting in Pancole on 24 August 2024 features extra inclusions to mark the occasion: a cruise with aperitif along the Arno River in Florence, a local birthday celebration and a special edition Exodus kitbag. Did you know you can travel by train to this trip? Find out more hereDiscover picturesque towns and delicious wines in Tuscany


Itinerary focusClassic Highlights
Group sizeSmall Group - max of 16 people
Age range18 years and up
Flights and transportAll internal ground transport included
Start CityPancole
End CityPancole

Travel Themes

  • Culinary & Wine
  • Cultural
  • Hiking & Walking
  • Trekking & Expeditions


  • Europe
  • Italy


  • Florence


  • Culture
  • Hiking

Trip includes

    • All breakfasts, five dinners, three wine tastings
    • All accommodation
    • All transport and listed activities
    • Tour leader throughout

Popular Trips


Travel Map

Day 1 Start in Pancole

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 ...

Day 2 Walk a section of the Via Francigena; afternoon local wine tasting

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;...

Day 3 Walk to Radda in Chianti

This morning, we enjoy a local history walk to the heart of the Chianti area, covering the scenic route from Pancole to Radda in Chianti. We cut through woodlands, where we can admire the emerald vineyard valleys. In the afternoon, we can taste the much-acclaimed chianti classico at a local winery.

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

After breakfast, we head to the centre of Siena for a day exploring this fascinating city. We have time to visit the numerous museums and stunning duomo (cathedral) and to relax in one of the many outdoor cafes in Piazza del Campo, home of the Palio horse race. Please...

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

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

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 t...

Day 7 Walk to picturesque San Gimignano with free time to explore Palazzo Comunale, Pinacoteca and Torre Grossa

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 b...

Day 8 End in Pancole

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

Want a tailor-made trip instead?

Your trip, your way, planned by an expert:

  • You choose budget, destinations, activities, transport & lodging type
  • Expert designs the itinerary for you, and once approved, takes care of logistics
Design custom trip

Dates & Availability

Price From $2,325
Price per day$291
Last Updated: 4/12/2024
Start Date
Finish Date
Double Standard
20 Apr 2024
27 Apr 2024
6 spots left
04 May 2024
11 May 2024
8 spots left
11 May 2024
18 May 2024
4 spots left
25 May 2024
01 Jun 2024
8 spots left
15 Jun 2024
22 Jun 2024
3 spots left
24 Aug 2024
31 Aug 2024
8 spots left
31 Aug 2024
07 Sep 2024
8 spots left
14 Sep 2024
21 Sep 2024
2 spots left
21 Sep 2024
28 Sep 2024
3 spots left
28 Sep 2024
05 Oct 2024
7 spots left

Check Current Availability, prices, specials with Exodus Travels.

The total tour cost includes the tour price (regular or promotional) and the compulsory local payment. The promotional price is subject to change. Check directly with the operator for the latest price offer. The tour operator requires you to pay only the tour price to purchase your travel. The compulsory local payment will be paid when you join the trip. All prices are based on double, twin or triple share occupancy. Solo passengers will be accommodated in a double, twin or triple room according to availability with a passenger(s) of the same gender. Single supplement only needs to be paid if the passenger does not want to share and requests their own room. Discounts can only be applied at the time of booking and cannot be added at a later date, regardless of any changes made to the original booking.

Prices may vary due to local taxes and trip seasonality. Click "Request Info" to inquire directly with the tour operator for the final trip price.

Exodus Travels Reviews & Ratings

4.7/5  Excellent


Oct 2018

Provided byExodus Travels

Come prepared

The walks were more challenging than we anticipated from their description Finishing the walk to Radda which for us at the ages of 72 and 64 was particularly chall...



Oct 2018

Provided byExodus Travels

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 bea...



Oct 2018

Provided byExodus Travels

excellent trip

Wonderful combination of walks, wine , villages and cities, with a nice group of people. Weather sunny but not too hot, allowing half day hilly walks in comfort an...



Oct 2018

Provided byExodus Travels

Beautiful Tuscany

We had an amazing time walking and sampling wines that we had never tried before but are now fans of. Our leader Liz Proctor was excellent, knowledgeable, tireless...



Oct 2018

Provided byExodus Travels

Totally Tuscany ...

One week of great walks , great hospitality and great food .. superb leader in Mark and combined with the warmth of the late summer sun we couldn’t ask for a bette...

Write a Review

Other Exodus Travels Reviews



Dec 2023

Written on

Exodus Discover Costa Rica is great for birders

Discover Costa Rica is a great itinerary, covering varied habitats around the country and staying 2 nights each at 6 centres. Their birdwatching specials are led by ...



Dec 2023

Written on

Thai Indochina Explorer

Such an amazing trip to experience so much of South Vietnam, Cambodia and Thailand (Bangkok only), in just 2 weeks. The local guides Trang (Vietnam), Channa (Cambodi...


Baltimore Chop

Feb 2024

Written on

We enjoyed our first trip to Costa Rica, especially hiking in the Monteverde cloud forest, relaxing on the beach at Manuel Antonio and seeing amazing plants, flowers, birds and animals at every turn.

This was the first time we have been to Costa Rica and the first time we have done an organized tour. We decided to join the tour for the convenience of planning, t...

Write a Review

Travelers also viewed

Tour Operator

Exodus Travels

View Profile

It is all about adventure. That is what Exodus was founded upon and what the company is still all about. Discovering countries, cultures, environments, cities, mountain ranges, deserts, coasts and jungles; exploring this amazing planet we all live on.

At Exodus, we know what makes you tick when it comes to holidays. It’s a desire shared by so many others. A yearning to visit new places and come home with a real sense of what they’re all about. This means delving into local traditions, cultures, cuisine, lifestyles – anything that contributes to its unique identity. At the same time, we always remember that we are only guests. So we travel courteously and respectfully, in smaller groups to minimise our impact, to ensure that every Exodus holiday is a beneficial experience for everyone involved.

This is a philosophy we take with us around the world, helping you reach some incredible destinations on 500 itineraries across over 90 separate countries. We also strive to provide as much flexibility and choice as we possibly can, making it simple for you to experience a very different holiday.

Exodus started life on 4 February 1974 when two friends got together to provide an overland truck to travel to the Minaret of Jam, deep in the heart of the Hindu Kush, the most inaccessible of the world’s great monuments.

All our office staff have a passion for travel and adventure, and between us we’ve notched up experience that spans 171 different countries. That’s not all. In their former lives, our team members have been professional archaeologists, wildlife guides, overland drivers, mountain leaders, diving and ski specialists and mountain bike gurus – so no-one is better placed to create tours that appeal to a wide range of specialist interests.

Their care in putting all the details in place really shines through too. Extensive planning, research, fact-finding and training are a sign of our commitment to providing a holiday where your enjoyment, value for money and safety come first. It’s a telling reason why we remain one of the leading worldwide adventure tour companies. It is no exaggeration to say that our tour leaders can make a world of difference to the enjoyment of your holiday – so we choose them carefully. The result is that, in 2013, 93% of our clients stated that their leader exceeded their expectations. Where possible, we train and employ local leaders because they can provide invaluable insights that enrich the trip. What’s more, this investment in local staff really helps us benefit both them and their community.

Why we love this operator
With a huge range of trip styles and themes, they cater to basically every type of traveler out there- even those with super specific interests.
What they’re known for
Global trips to both classic and exotic destinations with a focus on themed adventures, exciting physical activities and discovery of local culture.

About Travelstride

Find your perfect trip

An epic selection of pre-planned trips on every continent, for every style. Thousands of itineraries from over 1,000 trusted travel companies.

Save time

Use simple search and comparison tools to easily find the best trip. Don't sweat the logistics — travel providers plan for you.

Save money

Book directly with the operator. See inclusive packages for the best values, and get access to amazing deals.

Travel confidently

Read unbiased user reviews, pick the operator that suits your needs, and connect with them directly.


What's excluded

    • Travel insurance
    • Single accommodation (available on request)
    • Visas or vaccinations
    • Local taxes (approximately €10 per person, see Trip Notes)
    • Pre & Post Package
    • Extension Package


7 nights renovated farmhouse with panoramic swimming pool 5 days gentle walking and sightseeing Low altitude throughout Centre-based holiday,Surrounded by rolling Tuscan hills, Hotel Le Renaie occupies a privileged spot in the little village of Pancole, just 3mi (5km) from San Gimignano. Here, the Sabatini family has created an intimate, friendly retreat with just 25 air-conditioned rooms and plenty of places to mingle. Under the beautiful 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 excellent local wine. It's a popular stop for Pancole residents, so you know it's good. There are also games tables (table football, billiards and ping pong) 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 Pool opening dates are subject to local weather conditions and pool maintenance requirements; cooler months may not be suitable for swimming
Cancellation policy

The cancellation policies of this trip when booked through Travelstride are determined by the stated policies of the tour operator - Exodus Travels.

If you or any other member of your party decides to cancel a confirmed booking you must notify Travelstride in writing. Your notice of cancellation will only take effect when it is received in writing by Travelstride and will be effective from the date on which we receive it.

If You Cancel Your Holiday
You, or any member of your party, may cancel your travel arrangements at any time. Written notification from the lead name or your travel agent must be received at our offices. 

Since we incur costs in canceling your travel arrangements, you will have to pay cancellation charges as follows (see also the exceptions below): 

  • More than 42 days - No cancellation fee. Deposit can be transferred to a new booking departing within 2 years of date of travel of original booking. Any remaining balance will be refundedThis excludes all non-refundable costs as set out in clause 4 above (for example international and domestic flights and local services).
  • Between 41 and 21 days (inclusive) - No cancellation fee. Balance and deposit can be transferred to a new booking departing within 2 years of date of travel of original bookingThis excludes all non-refundable costs as further explained in clause 4 above (for example international and domestic flights and local services).
  • Between 20 and 15 days (inclusive) - 80% of the holiday cost
  • 14 days or less; or failure to join the holiday (inclusive) - 100% of the holiday cost

Certain trips may involve different cancellation charges; you will be advised if this is applicable to your holiday during the booking process.For Polar holidays, the following cancellation charges will be made for all Polar holidays. Period before departure in which you notify us: 

Cancelation charge

  • More than 133 days - Deposit only
  • 133 days or less (or failure to join the holiday) (inclusive) - 100% of the holiday cost

Notes (i) Your deposit is non-refundable, even if the cancellation charge calculated is lower than the deposit amount paid; (ii) If the reason for your cancellation is covered under the terms of your insurance policy, you may be able to reclaim these charges; (iii) certain travel arrangements may be subject to higher cancellation charges and could incur a cancellation charge of up to 100% of that part of the arrangements from the moment the booking is confirmed.

If You Change Your Booking

If, after our Booking Confirmation has been issued, you wish to change your travel arrangements in any way, for example your chosen departure date or accommodation, we will do our utmost to make these changes but it may not always be possible. Any request for changes to be made must be in writing from the lead name or your travel agent. You will be asked to pay an administration charge of $60, and any further cost we incur in making this alteration (including those charged by third party suppliers who provide the component parts of your booking).  You should be aware that these costs could increase the closer to the departure date that changes are made and you should contact us as soon as possible. Note: Certain travel arrangements may not be changeable after a reservation has been made and any alteration request could incur a cancellation charge of up to 100% of that part of the arrangements.

You can transfer your booking to another person, who satisfies all the conditions that apply to this booking, by giving us notice in writing at least 7 days before departure provided that the new lead passenger accepts the transfer and these Terms and Conditions. Both you and the new traveler are responsible for paying all costs we incur in making the transfer. Please bear in mind that certain airlines and other transport providers treat changes as a cancellation and charge accordingly, up to 100% of the cost for that part of the arrangement. Where applicable these charges will be passed on to you.

If We Cancel Your Booking

Exodus reserves the right to cancel an itinerary before departure for any reason whatsoever, including too few participants ,logistical problems, a Force Majeure Event (as defined in Section 8), or any other circumstances that may make operation of the trip inadvisable. All trip payments received will be promptly refunded, and this refund will be the limit of Exodus’s liability without any further obligation on Exodus’s part. Exodus is not responsible for any expenses incurred by trip members in preparing for the trip, including non-refundable or penalty-carrying airline tickets, special clothing, visa or passport fees, or other trip-related expenses.

If We Change Your Booking

  1. Changes to the price. We can change your holiday price after you’ve booked, only in certain circumstances. Changes in the price of the carriage of passengers resulting from changes to the cost of fuel or other power sources, the level of taxes or fees imposed by third parties including tourist taxes, landing taxes or embarkation or disembarkation fees at ports and airports, or exchange rates mean that the price of your travel arrangements may change after you have booked.

  2. Changes other than the price. It is a term of your booking that we are able to make changes to any aspect of your booking. If the change is insignificant, we will ensure that you are notified about it. Examples of insignificant changes include alteration of your accommodation to another of the same or higher standard. If we are forced by circumstances beyond our control to alter significantly any of the main characteristics of the travel services that make up your package you will have the rights set out below.

    2.1 - We will contact you and you will have the choice of accepting the change or having a refund of all monies paid. You can also accept an alternative holiday, where we offer one (we will refund any price difference if the alternative is of a lower value). We will tell you the procedure for making your choice. Please read any notification of changes carefully and respond promptly as if you do not respond to us within the timescale given your booking may be canceled.

    2.2 - If you choose to accept a refund then that is the only liability we have and we will not be liable for any further sums, compensation or otherwise and you are advised to adequately insure yourselves against cancellation for any reason

Please note that insurance premiums and amendments charges are not refundable in any circumstances. 

Once you have put down a deposit for a tour, you are unable to cancel and re-book within a promotional period and we reserve the right to amend the pricing on any new booking you make within that time. If you cancel a tour and book the same tour under a promotional code, we reserve the right to decline the booking.

Important Note: Certain arrangements may not be amended after they have been confirmed and any alteration or cancellation could incur a cancellation charge of up to 100% of that part of the arrangements in addition to the charge above.

If the reason for your cancellation is covered under the terms of your insurance policy, you may be able to reclaim these charges.

Where possible, we will deduct the cancellation charge(s) from any monies you have already paid to us.

For more additional details, see the booking conditions of TruTravels at the following web address: https://www.exodustravels.com/us/about-exodus/exodus-booking-conditions.

Travel Insurance
We strongly recommend purchasing travel insurance alongside your travel package to safeguard against unforeseen circumstances such as medical expenses, trip cancellations, and other contingencies. It offers you peace of mind and ensures you are prepared for unexpected events that may occur before or during your journey
Visa requirements
Visa requirements vary depending on your country of origin and your country of destination. It is your responsibility to familiarize yourself with the relevant requirements. For a handy tool that can help you quickly find the requirements, please visit this link .
Meals Included
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 the traditional Tuscan recipes. Vegetarian, vegan, gluten-free and dairy-free choices are available – please advise us of dietary requirements on booking.
Age Requirements
18 years and up
Additional Information
Seven nights in a 3* hotel with a swimming pool Five days gentle walking and sightseeing Low altitude throughout Option to travel by train to your adventure Option to book an extension package
Trip ID

Become a member

(it's free)
  • Save up to $700 per person
  • Access members-only specials
  • Personalize trip recommendations
Sign up and save
Top Tour Companies on Travelstride:
All 1,600+ companies >