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Take in the splendours of southern Tuscany, an iconic landscape of rolling hills, avenues of cypress trees and medieval villages on this cultural highlights tour with a foodie focus. Explore the captivating city of Siena, take a tour through the vineyards and olive groves of Chianti and taste your way around the hilltop towns of Montalcino, Pienza and San Gimignano.
7 nights comfortable hotel
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. Your tour leader plans to meet everyone at the hotel reception for a welcome meeting today at 6.30pm. After the meeting we'll head out on a brief orientation stroll taking in the beautiful Campo del Miracoli and the iconic Leaning Tower; stunning testaments to a time when Pisa was one of the Mediterranean's major maritime powers.
We'll then head out to a local restaurant for an included welcome dinner and our initiation into the cuisine of Tuscany.
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)
We head off after breakfast to the port city of Livorno, around 45 minutes drive from Pisa. Livorno is known for its seafood, its Renaissance-era fortifications and the canal-laced Venezia Nuova quarter. We'll spend time exploring the huge Neoclassical Central Market, Vettovaglie, the second largest indoor market in Europe with hundreds of stalls. It's the perfect place to kick off a week spent in appreciation of Tuscany's fantastic produce. Historically, peasants would come each morning from the nearby agricultural area of Gabbro to sell their produce and in the Gabbrigiane, the section of the market dedicated to vegetables and poultry, almost all of this is still sourced direct from the surrounding countryside. Livorno being a port city, the fish selection here is superb. The market is a great place to mingle among the Livornese, bartering and going about their everyday shopping. We'll enjoy a street food lunch sourced from the torteria stands, washed down with a regional wine or an authentic espresso.
After lunch we head to southern Tuscany and the classic panoramic landscapes of the Val d'Orcia; green rolling hills, hilltop towns, white gravel strade bianchi roads, avenues of cypress trees, vineyards and olive groves. Stopping off at the walled hilltop town of Montalcino, we'll have some free time to explore and the chance to enjoy a wine tasting of the famous Brunello di Montalcino wine that grows in the surrounding vineyards.
Tonight we stay in the walled, medieval village of Buonconvento that sits on the Via Francigena, an ancient pilgrimage route connecting Canterbury with Rome. You're free this evening to eat out in one of Buonconvento's restaurants. Dining here is generally simple with traditional local dishes including panzanella (a salad of stale bread, onion and tomatoes), pappa al pomodoro (a thick bread soup), pici con le criciole (pasta with breadcrumbs) and pappardelle sulla lepre (pappardelle with hare ragu).
Albergo Roma (or similar)
We'll take in the stunning Tuscan countryside today on a hike (approximately three kilometres, one hour) to a nearby farm, Pieve a Salti. With over 700 hectares given over to organic cereal production ( crops include oats, spelt, wheat and pulses) and a herd of cattle, we'll hear the story of how the Prandi family converted the farm to organic production and set up a production line that now supply mills, pasta factories, bakeries and supermarkets. We'll enjoy lunch in the restaurant here which serves up typical Sienese and Tuscan dishes using produce from the farm accompanied by wines from the area such as Brunello di Montalcino, Nobile di Montepulciano, and Chianti.
After lunch we head to Pienza, a classic hilltop town and jewel of Renaissance architecture that UNESCO declared a World Heritage Site in 1996. Pienza is known for its pecorino cheese and we'll indulge in 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. Pecorino is produced in quite modest quantities, around Pienza with only some 20 companies producing the cheese made from the milk of just 3,000 sheep.
After some free time in Pienza we head to the beautiful city of Siena for the next two nights.
Hotel Italia (or similar)
We've a full day today to enjoy the fabulous medieval city of Siena. 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 explore on foot on a guided walking tour. 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.
Cakes are synonymous with Siena and in the afternoon we'll pay a visit to a local pasticerria to taste and learn the stories behind traditional Sienese cakes such as ricciarelli (almond cakes with a soft centre covered with icing sugar), cantucci (crunchy cookies studded with almonds) and panpepato (a dense, dark, spiced, dried-fruit-and-nut-spiked cake). Later we'll split into smaller groups to visit the small family-run pasta shop Pasta Fresca Siena for a pasta making demonstration. Over 30 different types of fresh and dried pasta are produced here.
This morning we head to the magnificent Ricasoli Wine Estate, centred around the medieval Brolio Castle. The cellars are located at the foot of the castle and we'll enjoy a tasting here following our estate tour. Castelli di Brolio is the flagship chianti classico wine produced at the estate. We then head to the pretty little town of Greve in Chianti with its focal point the Piazza Matteotti surrounded on three sides by portico-covered boutique shops, artisans workshops and restaurants. It's a lovely place for a wander and enjoying an alfresco lunch. There's the option to visit the Pruneti olive oil mill and tasting rooms to learn all about the production of and taste some of the high quality extra virgin olive oils that are exported from here throughout the world.
We then head to San Gimignano, 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. It's fourteen medieval towers are a memorable sight as you approach. It's our base for the final three nights of the holiday and we stay in a historic property on the main square with a fabulous view of the surrounding countryside from its rooftop terrace. Please note that as our bus cannot access central San Gimignano we will need to walk 15 minutes from the bus checkpoint to our hotel. Luggage will be transferred separately by small vehicle.
Hotel La Cisterna (or similar)
This morning we head to the Fattoria Lischeto farm in the countryside close to the medieval walled town of Volterra. The 240 hectare farm was established by Giovanni Canas in the 1980s and is known for its cheeses, made from the milk of the 800 plus sheep that graze here on the organically managed pastures and fodder. We'll take a guided tour of the farm, learning all about the farming and production processes. Olive oil, wine and pasta are also produced here. We enjoy a lunch on the farm of authentic home-cooked produce, a blend of classical Tuscan and Sardinian recipes in keeping with traditional farmhouse cooking.
In the afternoon we head to Volterra with time here left free for personal exploration. Volterra's history dates from before the 8th century B.C. and it has remains from the Etruscan, Roman and Medieval periods. As well as visiting sites such as the 1st century Roman theatre, city walls and Etruscan acropolis, Volterra is famous for its alabaster, a light-coloured stone and many small workshops around the town sell objects crafted from this material.
This morning has been left free to enjoy San Gimignano. You may like to climb to the top of the Torre Grossa, the tallest of the town's towers. Originally there were 72 towers , some as tall as 50 metres, each built by San Gimignano's patriarch families in a competition and display of their wealth. Visiting the Vernaccia di San Gimignano Wine Experience at the Rocca di Montestaffoli, the town's highest point, is another recommendation. You'll learn all about the history and production of this intense white, whose grapes are grown in the Val d'Elsa and which was Italy's first DOC wine. And of course a tasting is part of the Experience.
After lunch we'll meet up to visit and indulge in an ice cream from one of San Gimignano's most famous gelateria, Dondoli. Sergio Dondoli's gelato has won many an award and is renowned for its use of high quality Italian grown ingredients.
We'll then head to Fattoria San Donato, a family-run farm producing mainly Vernaccia wines and olive oil alongside ancient grains. We will take part in a hands-on cooking class with Federica and be introduced to traditional preparation techniques and ingredients alongside tales from the farm. We will enjoy our final farewell dinner tonight at the farm, being able to enjoy the fruits of our labours alongside other fare.
Departing San Gimignano this morning we drive to Pisa Galileo Galilei International Airport (PSA) where the tour ends at 8.00 am. The earliest time you should book a flight to depart today is 10.00 am. (Please note that the 7th May 2023 and 21st May 2023 departures will end at the airport at 10.00 am and the earliest time your flight should leave is 12.00 pm). If you have time to pass before your flight departs, there is an inexpensive left luggage facility at the airport and the Pisa Mover rail shuttle will take you in to the centre of Pisa in just a few minutes.
April/May and October/November are pleasantly warm. June to 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 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. Greve in Chianti - olive oil tasting: approximately €20 EUR pp dependant on number of oils selected. San Gimignano - Torre Grossa: €9 EUR pp Vernaccia di San Gimignano Wine Experience: €30 - €65 EUR pp depending on Experience selected.
Bring light and comfortable clothing that can be layered according to the temperature. July and August can be extremely hot, but early and late in the season Italy can be chilly so go prepared with clothing to suit drops in temperature and rain showers. Light rainwear may be needed at any time of year, and a warm fleece/jacket is recommended for cooler evenings and nights.
Comfortable lightweight walking shoes or trainers are recommended for waking tours and sightseeing, plus sandals for relaxing.
You'll need one main piece of baggage and a small daypack for when you're out and about exploring. As you'll be taking care of your own luggage, it's really important for your enjoyment not to overload yourself.
Sunscreen, sunglasses and a sun hat are advised. A power bank may be useful if you'd like to use or charge your phone whilst travelling. We advise you 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.
In Pisa we stay at the Hotel Bologna, a centrally located four star hotel around 10 minutes walk from from the Central Station where the Pisa Mover from the airport terminates, 15 minutes from the Piazza dei Miracoli where the Leaning Tower is located. The Albergo Roma in Buonconvento is a newly refurbished bijoux three star property with just 10 rooms on a quiet street in the centre of historic Buonconvento. With a full group some customers may be accommodated in sister property Hotel Ghibellino a 5-minutes walk away. Hotel Italia in Siena is a comfortable three-star hotel with a reputation for its friendly welcome. Rooms are well appointed and the breakfast buffet features home-made pastries. It's around 20 minutes walk from the Piazza del Campo and close to the fresh pasta shop we visit. Hotel la Cisterna overlooks one of San Gimignano's main squares, the ancient Piazza della Cisterna and has historic roots dating back to medieval times when the building was used as a resting place for pilgrims on the Via Francigena, an ancient route connecting Canterbury in the UK with Rome. It's lovely roof terrace enjoys commanding views over the surrounding countryside. As our bus cannot access central San Gimignano we will need to walk 15 minutes from the bus checkpoint to our hotel. Luggage will be transferred separately by small vehicle.
We have purposely not included all the meals on this trip to allow you the opportunity to experience a variety of different restaurants of your choice. On many evenings the trip leader will facilitate a group dining experience for those wishing to join in. There are also some Michelin recommended dining experiences available on this trip. Those with stars would need to be booked well in advance of the trip. San Gimignano: Linfa https://www.mktn.it/linfa - 1 Michelin Star - average 125-145 euro per person per meal Colle Val d'Elsa (close to San Gimignano): Arnolfo https://www.arnolfo.com/ - 2 Michelin Stars - average 150-180 euro per person per meal Siena - there are several non-starred restaurants recommended in the Michelin guide: Particolare - https://particolaredisiena.com/ Mugolone - https://www.ristorantemugolone.it/ Babazuf - http://www.osteriababazuf.com/index.php/it/home/ La Taverna di San Giuseppe - https://www.tavernasangiuseppe.it/
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 or Canadian citizens. Other nationalities should consult their local embassy or consular office. All visa information is subject to change. You should confirm all visa related questions with the relevant embassy prior to departure.
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.