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  • Monday 9.00am - 7.00pm GMT
  • Tuesday 9.00am - 7.00pm GMT
  • Wednesday 9.00am - 7.00pm GMT
  • Thursday 9.00am - 7.00pm GMT
  • Friday 9.00am - 7.00pm GMT
  • Saturday 9.00am - 5.30pm GMT
  • Sunday 10.00am - 4.00pm GMT
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Southern Tuscany Walking and Wine

Italy - Trip code LTY Walking and Trekking
Carbon Footprint Leaf Icon
181Kg of CO₂e
Average carbon footprint per person
Carbon Footprint
You deserve to know everything about your holiday, from what is included, what to expect and every kilogram of CO2 emitted on average per person along the way.

We've partnered with ecollective to measure the carbon footprint of this tour based on an average group size. Find out more about how we calculate this and why we think it's important here.


Days 8
Deposit From CHF 211
Price from CHF 2109
Flights not included

Why book this trip?

A walking holiday that takes in the splendours of southern Tuscany, an iconic landscape of a rolling hills, avenues of cypress trees and medieval hilltop towns. Ramble through the vineyards of Chianti, along ancient pilgrimage trails and explore the captivating cities of Siena and Florence.

  • Wine tastings - Sample some of Italy's finest wines from Chianti to Brunello
  • Hilltop towns - Discover San Gimignano, Pienza, Montepulciano and Montalcino
  • Local cuisine - Enjoy the fresh produce and delicious flavours of Tuscany
  • Included meals

    Breakfast: 7

    Lunch: 2

  • Trip staff

    Explore Tour Leader / Trek Guide

  • Transport



  • i


    2 nights comfortable guesthouse

    5 nights comfortable hotel

  • i

    Walking grade:

    Leisurely and Moderate

  • i

    Group Size:

    Trip maximum 16
    Explore Average 11


Itineraries on some departure dates may differ, please select the itinerary that you wish to explore.

Day 1 - Trip starts today in Pisa

The trip starts today in Pisa. The city's famous leaning tower and beautiful Campo del Miracoli are stunning testaments to a time when Pisa was one of the Mediterranean's major maritime powers.

The Leader plans to meet everyone at the hotel for a welcome meeting today at 6.30 pm and for those that wish, there is the chance to go out for dinner afterwards. Should you miss the meeting, your Leader will inform you of any essential information as soon as you catch up.

There are no activities planned today, so you are free to arrive in Pisa at any time. If you would like to receive a complimentary airport transfer today, you'll need to arrive into Pisa Galileo Galilei International Airport (PSA). Your driver will greet you on arrival at the airport (look for your name or an Explore signboard) and take you on to our hotel on the banks of the Arno River, a short journey of around 10 minutes.

If your flight arrives earlier in the day and you wish to explore this compact city on foot, the central area is less than a kilometre's walk from our hotel.


Grade: Comfortable Hotel

Single room available

Meals Provided: None

Day 2 - Walk to San Gimignano; wine tasting

This morning we drive towards San Gimignano, parking our bus in the rolling countryside outside of the town. We set off on a hike along part of the Via Francigena (an ancient pilgrimage route running all the way from Canterbury to Rome) along a wide gravel track past vineyards and rural houses. The thirteen medieval towers of San Gimignano are often in sight in the near distance. San Gimignano is a beautifully preserved example of a classic Tuscan medieval town. It prospered during the 12th and 13th centuries, until a combination of local aristocratic rivalry and the arrival of the Black death devastated trade. We will have some free time to explore the town, have a relaxing lunch in one of many cafes and perhaps walk up to the Torre Grossa, or visit the Duomo.

In the early afternoon we'll head back on foot to the bus along a scenic route via Santa Lucia. En route we'll stop to visit the Sovestro winery for a tasting of some of the local San Gimignano white wine. We then continue to Monteriggioni, a beautifully preserved fortified hill-top village, where we can walk around the walls. Our base for the next two nights is Castellina in Chianti, a country town with Etruscan and Roman origins. Castellina lies at an altitude of around 580m in the heart of the Chianti Hills, an area famous for its wine.

Note: Depending on the size of the group we may be accommodated across two properties 5 minutes walk apart.

Today's gently undulating ten kilometre walk is expected to take around three-and-a-half hours.


Grade: Comfortable Guesthouse

Single room available

Swimming pool available

Meals Provided: Breakfast

Day 3 - Walk in the heart of Chianti country

After breakfast we drive close to the town of Volpaia, near to Radda in Chianti. Our walk heads out from the small chapel of Santa Maria Novella and slowly climbs through vineyards and along marked trails up into the hills of Chianti to the picture perfect village of Volpaia. We then follow local village paths and old drovers' roads, cutting through the vineyards and fields of the villa of Castelvecchi. Finally, we descend back to Santa Maria Novella for a well-earned rest in the olive groves of the church and our picnic lunch. A short bus ride takes us to Radda for some time to explore and look around and perhaps have a gelato. Once back in Castellina there's the option to head out to a wine tour and tasting at the Rocca della Macie wine estate where the famous Chianti Classico is produced.

Today's seven kilometre walk is expected to take around four hours with a total ascent and descent of 150 metres.


Grade: Comfortable Guesthouse

Single room available

Swimming pool available

Meals Provided: Breakfast & Lunch

Day 4 - Visit medieval Siena; drive to Pienza in southern Tuscany

Our final destination today is Pienza in southern Tuscany, but we will stop for most of the day in the fabulous medieval city of Siena where our time is free to explore the market and other sights. With its magnificent Gothic architecture, Siena was once a rival to Florence in power and trade, the city controlled the trade routes between France and Rome, as well as the southern Tuscan wool industry. Today it stands as a classic Italian city, with its magnificent central square, Il Campo, and the awe inspiring grandeur of the Duomo overlooking the Via di Citta. The city centre is traffic-free, making it ideal to wander around on foot, soaking up the many intriguing sights. The focal point is the Piazza del Campo, a semi-circular area surrounded by ancient buildings, and overlooked by a 100 metre bell tower, the Torre del Mangia. The Piazza is also used for a horse race twice a year - the famous Palio, when horses and their riders hurtle dangerously around the square to the delight of the crowds.

Pienza, our base for the next three nights, is a classic hill-top town and jewel of Renaissance architecture that UNESCO declared a World Heritage Site in 1996.


Grade: Comfortable Hotel

Single room available

Swimming pool available

Meals Provided: Breakfast

Day 5 - Walk to Montepulciano via Montichiello

Our walk today heads downhill from Pienza on typical 'strade bianche', the white gravel roads of Tuscany. We head towards the village of Montichiello, a lovely medieval walled village where we will have a well earned break and admire one of the most famous cypress tree avenues in the whole of Tuscany (and the one on most of the postcards!) Retracing our steps a little way downhill, we pick up our trail heading past vineyards, enjoying some enchanting views across the surrounding countryside as we make our way towards the temple of San Biagio on the hillside below the town of Montepulciano. Founded by Antonio Sangallo the Elder in the 16th century, this glorious church was, at the time, the largest outside of Rome and is considered by many to be one of the finest Renaissance buildings in Italy. Continuing up the hill into the town, we head via the Piazza Grande, Montepulciano's flamboyant main square. Perched on a 605 m high limestone ridge and encircled by Renaissance-era walls and fortifications, Montepulciano is a major producer of food and drink; renowned for its pork, cheese, 'pici' pasta, lentils, and honey and not least its wine. Connoisseurs consider its Vino Nobile among Italy's best. Before heading back to Pienza by local bus, we will have time to explore some of the underground cellars of Montepulciano with the option of enjoying a wine tasting.

Today's 12 kilometre walk is expected to take around four-and-a-half hours with a total ascent of 350 metres.


Grade: Comfortable Hotel

Single room available

Swimming pool available

Meals Provided: Breakfast

Day 6 - Hike in the Val D'Orcia to hill-top Montalcino

Today we drive from Pienza to San Quirico along a panoramic road where some of the scenes from the film 'Gladiator' were filmed. San Quirico D'Orcia is a beautiful town that lies along the Via Francigena pilgrimage route and we will have some time here, before we set out on our walk. Descending from the town we cross the Asso river and follow undulating trails with wide open views of the classic Val D'Orcia. Vineyards surround us and the towers of Siena are visible on the Horizon. Our final destination is the hill-top town of Montalcino located at just over 500m. We have some free time to explore and the chance to enjoy a wine tasting of the famous Brunello di Montalcino wine.

Today's 12 kilometre walk is expected to take around five hours with a total ascent of 450 metres.


Grade: Comfortable Hotel

Single room available

Swimming pool available

Meals Provided: Breakfast & Lunch

Day 7 - Drive to Florence; orientation walk

Leaving the rolling hills of southern Tuscany behind we head for our final destination of the holiday, the fabulous city of Florence. The spiritual home of the Renaissance, Florence is considered by many to be one of the most beautiful cities in Italy. On arrival our leader will take us out on an orientation walk with the rest of the day left free to explore further. Highlights include the Ponte Vecchio, the oldest and most famous bridge in Florence and the only one that was not demolished during the German retreat of 1944 and the Cathedral of Santa Maria del Fiore with its giant dome that dominates the city skyline. Early evening is the perfect time to walk up to the Piazzale Michaelangelo for a great view over the city.


Grade: Comfortable Hotel

Single room available

Meals Provided: Breakfast

Day 8 - Trip ends in Florence

The trip ends after breakfast this morning at our hotel in Florence.

There are no actvities planned for today and you are free to depart at any time. If you are departing later in the day luggage storage facilities are available at our hotel.

If you would like to receive a complimentary airport transfer today, you'll need to depart from either Pisa Galileo Galilei International Airport (PSA) or Florence Peretola Airport (FLR). If departing from Pisa Airport your trip leader will arrange the transfer , providing you with a ticket for the public shuttle bus service direct from Florence Centrale Railway Station to Pisa Airport. A taxi transfer from our hotel to the shuttle bus departure point will also be provided for you. The total journey time is around 70 minutes. If you are departing from Florence Airport you will be transferred from our hotel to the airport by taxi, a journey of around 30 minutes.

Meals Provided: Breakfast

Trip information

Climate and country information



April/May and October/November are pleasantly warm. June/September are the hottest months. Showers are common in Autumn.

Time difference to GMT



2 Pin Round


Roman Catholic



Budgeting and packing

Optional activities

The following excursions and/or activities are usually available and may be arranged locally. Estimated costs are provided below for guidance only, are on a per person basis unless shown otherwise, and may depend on the number of participants. Prices quoted are correct as of the date these tour notes were originally issued but may change at any time due to currency fluctuations. Please note: These activities are booked and paid for direct with the supplier and do not form part of your Explore holiday contract.

Montalcino - Wine tasting €10.


Take light and comfortable clothing that can be layered according to the temperature. July and August are the hottest months whilst early and late in the season go prepared with clothing to suit drops in temperature and possible showers. Light rainwear may be needed at any time of year, and a warm fleece/jacket is recommended for cooler evenings and nights.


We recommend you bring lightweight walking boots, make sure that your boots are worn-in and comfortable before the start of the trip. Also trainers or sandals for relaxing and general wear. We suggest that on international flights you either carry your walking boots in your hand luggage or wear them - should your luggage be lost or delayed, your own boots are the one thing that will be irreplaceable.



Luggage: On tour

One main piece of baggage and daypack.


Bring walking poles if you use them, a water bottle, insect repellent, sunglasses and sunscreen. A torch is useful in case of powercuts and navigating dimly lits streets at night.


Explore leader
Tipping isn't compulsory, and we work hard to ensure that our leaders all receive a fair wage. You may however, want to recognise a leader that has done a great job or really added to your trip by giving them a tip. We're often asked about the recommended amount. It is a tricky one, and down to personal preference, but we would recommend £15 to £20 per person per week as a guideline.


Food and drink

The costs for meals may vary depending upon location, type of restaurant and number of courses eaten and so the prices given are an average guide. Local restaurants located off the beaten track may be less expensive, whereas an upmarket restaurant located in the centre of a major city may charge more.

Lunch price
£10.00 - 15.00
Dinner price
£20.00 - 25.00
Beer price
£2.00 - 4.00
Water price
£1.00 - 2.00
Foreign Exchange
Local currency
Recommended Currency For Exchange
Where To Exchange
We recommend that you change any currency into Euros prior to arrival. Bureau de Change are generally only found in major cities and large airports.
ATM Availability
Major towns.
Credit Card Acceptance
Larger hotels and restaurants.
Travellers Cheques
Only in major towns. Please note, the exchange rate for cash and Travellers Cheques is poor.
Transport, Accommodation & Meals

Transport Information

Minibus, Train

Essential Information

Government Travel Safety Advice

We strongly recommend that you check your government's travel advisory for up-to-date information and advice about your destination: safety and security, entry requirements, health, local laws and customs. For UK citizens, check the latest Foreign, Commonwealth & Development Office advice.

Please refer to our COVID-19 entry requirements page for any country-specific conditions of entry. Whilst we strive to update this on a regular basis we recommend you also check the FCDO website for the latest advice on entry requirements in this fast-evolving situation. Information can change at any time.

Under 18 immigration guidance

Please note that some countries require proof of parental consent when travelling overseas with under 18s. Please check requirements with the relevant embassy or consular office well in advance of travel if this applies to your party.

Price Guarantee

Once your booking has been confirmed we guarantee the price will not increase, whatever the circumstances. Before booking please ensure you have read our important tour pricing information.Booking Conditions

Visa and Passport Information

Italy: Visas are not required by UK, E.U Nationals, Australian, New Zealand, US and Canadian citizens. Other nationalities should consult their local embassy or consular office.

If you do require assistance in obtaining a visa then you may be able to apply through Explore's recommended visa service in the UK, Travcour. See to download the relevant visa application for your trip, if applicable (UK citizens only), along with details of how to apply for your visa through Travcour. The Team at Travcour will be happy to answer specific questions relating to visa applications, please call them directly on 0208 5431846.

It is your responsibility to ensure that you are in possession of a full passport, with the correct validity for your chosen destination.

Booking conditions

Before booking your Explore trip, please ensure that you read both our Essential Information and Booking Conditions.

Minimum age restrictions

For our group tours, the minimum age is 16. The minimum age on Family trips varies between 7 and 11 - please check the 'Family information' section of the trip page for more information. 

Your safety and enjoyment on tour

We want everyone to have a safe and enjoyable holiday, so we ask you to confirm when booking this trip that you are fit and able to fully participate in all elements of the itinerary. If you have any concerns about your fitness or ability to complete any of the activities, please get in touch with our Customer Relations team at as soon as possible. Our tour leaders are trained and experienced in managing differing abilities within a group, but if they have concerns about a group member’s ability to safely participate in any element of the itinerary or believe someone’s presence could affect the safety or enjoyment of the holiday for others, in accordance with our Booking Conditions our tour leaders have the authority to ask an individual to miss an activity or activities. This decision would never be taken lightly, but on the rare occasions our tour leaders ask someone to sit out part of the tour, refunds will not be offered and individuals may be liable for additional costs incurred. 


Find out more about Trip Transfer Terms and Conditions before you book.

Booking a land only package with Explore

Customers who have chosen to book on the ‘Land Only’ arrangements of our tour, please ensure that you have checked your tour specific ‘Joining Instructions’ prior to booking your own travel arrangements. Your joining instructions can be found below in the dates and prices information. 

You may also be eligible for the Free Explore Transfer.

Joining Tour Abroad

Customers booked on the ‘Land Only’ arrangements will receive a Free Transfer, provided you arrive and depart on the tour only itinerary start and end dates. The complimentary transfers will be arranged from the Explore designated airport or train station to your trips joining point, and then back from the ending point to the designated airport or train station. Generally the airport or station that Explore have selected will be the one that is closest to the town or city where the trip starts, or the one nearest to the joining point. It will be either an airport or train station but not both.

The exception to this rule is customers who are booked on a tour where the joining and ending point is at the designated airport or train station.  

Free transfers are not available for Self-Guided, Polar, Tailormade or Tours for Churches customers.

If you are not eligible for the Free Transfer then you will need to make your own way through to the joining and ending point. On a majority of our tours Explore will be able to provide a private transfer at an additional cost. Please ask for a quote at the time of booking.  

For more information regarding the Explore Free Transfer click here


It is a condition of booking with Explore that you have adequate valid travel insurance. It is your responsibility to arrange appropriate travel insurance and ensure you have read and understood the full terms and conditions of your travel insurance policy to ensure that you are covered for all activities you intend to undertake whilst on the tour, including all optional activities. Your Insurance Policy must fully cover you for medical expenses and emergency repatriation to your home country. Please ensure your policy includes medical emergency helicopter evacuation in the event of illness or injury and covers the entire duration of your holiday. If you are trekking at altitude please ensure that there is no upper altitude limit which may limit or exclude cover for your trip. The cost of many of our Polar Voyages will exceed the capped amount covered by standard insurance premiums and you will be required to pay an additional premium to cover the full value of your trip. Please ensure that you are covered for the full amount of your holiday cost, as insufficient cover could invalidate a claim under the policy. Medical and repatriation insurance cover is not mandatory for UK residents who are travelling on trips within the United Kingdom.
Read more information about what travel insurance is required.

Flight information

Explore offers a wide range of flexible flying options to make joining and leaving our trips easy. Read more about them here.

Flight Information

You are able to book this tour on a 'land only' basis or as a ‘flight inclusive’ package. Your flight inclusive package will be fully protected by the Civil Aviation Authority (CAA) ATOL protection scheme.


Booking a flight inclusive package with Explore

We have a good selection of flights not only from London but from many regional airports around the UK allowing us to compare fares between scheduled carriers as well as low cost and charter airlines. Our dedicated flights team will match the best flight options to your arrival and departure airport.

On our website we display a UK flight inclusive package guide price which is generally based on a London departure. To avoid paying supplements or to secure your preferred flight option, we recommend booking as early as possible, especially for peak travel dates.

Maximum altitude (m)




Nothing required. Tetanus recommended. Please check the latest requirements with your travel clinic or doctor prior to departure. The above is not an exhaustive list. Further information regarding vaccinations and travel health advice can be found by following the NHS and NaTHNaC links at Explore Travel Health and from your local healthcare provider. Visa and vaccination requirements are subject to change and should be confirmed by you before travelling.

Walking and Trekking information
Walking grade
Leisurely and Moderate
Trek details
Walks on 4 days for between 3.5 to 5 hours.You will be walking on a mix of strade bianche, compacted gravel roads typical of Tuscany, as well as farm trails and mule tracks on undulating hilly terrain.
Max walking altitude (m)
Additional Information

Dates, prices and booking

📢 Prices may change - book now and today's trip price is guaranteed in our price promise

📅 2024 dates are landing. Can't see your preferred dates? Sign up here to be notified when they are live.
Sun 23 Apr 2023 - Sun 30 Apr 2023 Guaranteed departure
LTY_2023 1 space available
CHF 2240
was Save
+CHF 472
LTY_2023 1 space available

Add a flight with Explore

  • Full Explore refunds in the event of FCDO cancellations or major disruption at your UK departure airport
  • Carbon neutral flights – Gold Standard offsetting included
  • Rearranged flights and transfers in the event of delays, missed connections, or cancellations (including accommodation overseas)
  • ATOL protected
  • No surcharge guarantee
Sun 21 May 2023 - Sun 28 May 2023 Guaranteed departure
LTY_2023 5 spaces available
CHF 2109
was Save
+CHF 472
LTY_2023 5 spaces available

Add a flight with Explore

  • Full Explore refunds in the event of FCDO cancellations or major disruption at your UK departure airport
  • Carbon neutral flights – Gold Standard offsetting included
  • Rearranged flights and transfers in the event of delays, missed connections, or cancellations (including accommodation overseas)
  • ATOL protected
  • No surcharge guarantee


Award Winning Explore Leaders
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Price Guarantee Promise
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Airport Transfers
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