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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.
Explore Tour Leader
7 nights comfortable hotel
Leisurely and Moderate
Trip maximum 16 Explore Average 11
Itineraries on some departure dates may differ, please select the itinerary that you wish to explore.
The trip starts today in Pisa at our centrally located hotel. 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.
Your Tour 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.
Pisa Airport is just a few kilometres from the centre of town so it's easiest to organise your own transfer to the joining hotel; an arrival transfer is not included with this tour. The Pisa Mover is an automated shuttle train that departs from the airport to Pisa Central Station approximately every 10 minutes with a journey time of 5 minutes. Tickets cost €5 Euro. It's a 10 minute walk from here to our hotel. Allow €15-20 Euro for a taxi from the airport to hotel, there is a taxi rank outside the terminal building.
We won't be climbing up the Leaning Tower so if that's on your wish list or you'd like to explore Pisa in greater depth, be assure to arrive earlier in the day or why not book an additional pre-tour night in the city. Pisa is a compact city and very easy to explore on foot.
Hotel Bologna (or similar)
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 cycle trail,(the Via Francigena is an ancient pilgrimage route running all the way from Canterbury to Rome), along a wide gravel 'white' track typical of the region, past vineyards and rural houses. The fourteen 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 hilltop 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, the tallest of the town's towers or visit the Duomo.
In the early afternoon we'll head back on foot to the bus. It's a short drive to the first wine tasting of the holiday at the nearby Sovestro winery. The Failli family produce both the local San Gimignano Vernaccia white wine as well as Chianti reds. We then continue to our base for the next two nights, 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.
Today's leisurely-grade 10 kilometre walk is expected to take around three-and-a-half hours with a total ascent and descent during the course of the walk of 365 metres.
Hotel Colle Etrusco Salivolpi (or similar)
We head out from our hotel after breakfast this morning on an undulating route that takes us through the countryside south from Castellina past vineyards, fields and olive groves. Much of the trail is on 'strade bianchi', the rural backroads that wind their way across the countryside of Tuscany and Umbria, formed from white compacted limestone gravel. Our destination is the beautiful Castello La Leccia winery which produces organically cultivated Chianti Classico wines. We'll enjoy a tasting of Chianti wines and a light lunch of local cheeses and cold cuts.
We drive back to our hotel in the afternoon and the rest of the day is left free. You can explore the charming village of Castellina; the centre is just a few minutes walk from the hotel. Sit back and observe local life while enjoying an espresso or aperitivo at a pavement cafe, or maybe indulge your sweet tooth with a gelato. Our historic hotel has a lovely garden with a swimming pool (open in season), a great place to relax and read a book.
Today's moderate-grade 14 kilometre walk is expected to take around four hours with a total ascent and descent during the course of the walk of 420 metres.
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 Wednesday 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.
Relais II Chiostro di Pienza Hotel (or similar)
Our walk today makes a panoramic loop through the stunning countryside around Pienza and is known locally as the 'Gladiator hike' as scenes from that movie were filmed here. Along the route we pass by the iconic Vitaleta chapel, a tiny, secluded building perched on a hill framed by cypress trees.
Pienza is known for its pecorino cheese and in the afternoon there's the option to enjoy a cheese tasting at the Armellini family's cheese shop in the town. Pecorino is produced from sheep of Sardinian stock, many farmers having relocated here from Sardinia in the 20th century.
Today's 10 kilometre leisurely-grade walk is expected to take around three hours with a total descent and ascent of 350 metres.
Today we drive from Pienza to San Quirico D'Orcia a beautiful town that lies along the Via Francigena pilgrimage route. We'll have time for a look around 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. We'll enjoy a picnic lunch along the trail. Our final destination is the hilltop town of Montalcino located at just over 500 metres above sea level. We have some free time to explore and the chance to enjoy a wine tasting of the famous Brunello di Montalcino wine.
Today's 13 kilometre moderate-grade walk is expected to take around five hours with a total ascent of 523 metres and descent of 383 metres.
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 (outside only) 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.
Classic Hotel Florence (or similar)
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). The transfer is provided by train or tram, our hotel is within a short walking distance from Florence Centrale Railway Station. If departing from Pisa Airport your tour leader will provide you with tickets for the train direct from Florence Centrale Railway Station to Pisa Centrale Station and then on to the airport on the Pisa Mover rail shuttle. The total journey time is around 90 minutes. If you are departing from Florence Airport you will be provided with a ticket for the T2 tram which runs direct from Florence Centrale Railway Station, a journey of around 20 minutes.
Total distance : 28 miles
April/May and October/November are pleasantly warm. June/September are the hottest months. Showers are common in Autumn.
2 Pin Round
Pisa - Leaning Tower; timed tickets can be purchased online in advance at https://www.opapisa.it/en or on site €20 pp San Gimignano - Torre Grossa: €9 EUR pp Pienza - cheese tasting: €12 pp 4/5 cheeses with bruschetta, olive oil and water Montalcino - wine tasting: a 3-wine tasting ranges from €20 - €33 EUR pp depending on the quality of the wines selected. Appetizers such as cheese and cold cuts included.
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. Our hotels in Castellina and Pienza both have swimming pools so you may wish to bring swimwear.
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.
One main piece of baggage and daypack.
Bring walking poles if you use them, insect repellent, sunglasses and sunscreen. Bring a water bottle for day to day use. We have a partnership with Water-to-Go, who have developed a filtration system that eliminates over 99.9% of all microbiological contaminants. This allows you to drink from any tap, including on trains, or even streams and lakes. You can purchase your own Explore branded bottle with the discount code EXPLORE15.
Historic Hotels In Castellina-in-Chianti we stay at the charming Hotel Colle Etrusco Salivolpi. A quarter of a century ago the Falassi and Orlandi families established their hotel in two farmhouses dating back to the 1400s. The cosy and comfortable rooms have been decorated in a traditional Tuscan country style with antique furnishings and open beam ceilings. All of the en-suite rooms come equipped with tea and coffee making facilities, a safe, hairdryer, flat screen television, wi-fi, air conditioning, pool towels and a bathrobe. There's a lovely garden for relaxing in and a swimming pool (open in season). https://hotelsalivolpi.com/en/ The Relais Chiostro di Pienza is a former Franciscan convent dating back to the 13th century located in the hilltop town of Pienza. Each en-suite room has a unique character and enjoys views either over the Cloister, Pienza's historic centre or the hills of the Val d'Orcia. All are equipped with a hairdryer, flat screen television, wi-fi, air conditioning and pool towels. It has a swimming pool (open end of May to mid September) and panoramic terrace, the perfect place to relax with a cool beer or spritz after walking. https://www.relaisilchiostrodipienza.com/en
Can you drink the water?
It is generally possible to drink the local tap water, therefore to reduce the need for single-use plastic bottles we recommend you bring a refillable water bottle with you. Your leader will advise you on refill points each day.
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.
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.
Once your booking has been confirmed we guarantee the price will not increase, whatever the circumstances. However, please note that if you voluntarily make any changes to your booking including changing your trip or departure date, any additional costs or charges incurred will not be covered. Before booking please ensure you have read our important tour pricing information.Booking Conditions
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 www.travcour.com 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.
Before booking your Explore trip, please ensure that you read both our Essential Information and Booking Conditions.
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.
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 Polar 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.
Explore offers a wide range of flexible flying options to make joining and leaving our trips easy. Read more about them here.
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.
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.
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.