A Taste of Tuscany - Hilltop Towns and Vineyards

Land Tour

7 days

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A Taste of Tuscany - Hilltop Towns and Vineyards
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  • Itinerary
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$AUD 641 per day

Departure: Pisa, Italy

Arrival: Pisa Airport, Italy

Take in the splendours of southern Tuscany, an iconic landscape of rolling hills, avenues of cypress trees and medieval villages on this cultural 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.

Val d'Orcia - Visit medieval hilltop towns set amongst a landscape of rolling hills and vineyards, stopping to enjoy wine tasting and tasting local dishes
Wine tastings - Sample some of Italy's finest wines from Chianti to Brunello.
Farm-to-table dining - Visit an agriturismo to enjoy fresh produce and delicious flavours at their source.

Highlights
Sample some of Italy's finest wines and dine on delicious Tuscan regional specialites|Explore captivating hilltop towns, Medieval San Gimignano and Siena|Visits to food and wine producers and tasting fresh produce at source

Tour information
Transport: Bus
Tour staff: Driver(s), Driver(s)
Meals :Breakfast 7, Lunch 3 & Dinner 2

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Itinerary
Day 1 - Join trip in Pisa; orientation tour followed by welcome dinner
Our tour starts today in Pisa at our centrally located hotel.
Our tour leader plans to meet everyone at the hotel reception at 6.30pm for a welcome meeting. 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.
An airport transfer isn't included in this trip but it's easy to get to Pisa Airport by yourself. 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. It's a 10-minute walk from here to our hotel. If you'd prefer to take a taxi, there's a rank right outside the terminal building - the journey should cost around €15-20.
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.
Day 2 - Central Market tour in Livorno with street food lunch. Visit hilltop Montalcino, optional tasting of Brunello wines
We'll head off after breakfast to the port city of Livorno, around a 45-minute 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 directly 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'll 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'll stay in the walled, medieval village of Buonconvento that sits on the Via Francigena, an ancient pilgrimage route connecting Canterbury with Rome. This evening, you're free 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 tomats), pappa al pomodoro (a thick bread soup), pici con le criciole (pasta with breadcrumbs) and pappardelle sulla lepre (pappardelle with hare ragu).
Day 3 - Ramble to agriturismo for lunch of local organic produce; cheese-tasting in Pienza
We'll take in the stunning Tuscan countryside today on a hike (approximately 3 kilometres/1.8 miles, 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'll 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'll head to the beautiful city of Siena for the next two nights.
Day 4 - Guided walking tour in Siena; pasticerria and pasta shop visits
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 huge 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.
Day 5 - Wine estate tour and tasting in Chianti; optional olive oil tasting
This morning, we'll 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'll 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, artisan 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'll 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. Its fourteen medieval towers are a memorable sight as you approach. It's our base for the final three nights of the holiday and we'll stay in a historic property on the main square with a fabulous view of the surrounding countryside. Please note that as our bus cannot access central San Gimignano we'll need to walk 15 minutes from the bus checkpoint to our hotel. Luggage will be transferred separately by a small vehicle.
Day 6 - Farm tour and lunch at an agriturismo; visit to Medieval Volterra
This morning, we'll 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'll 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'll 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 that sell objects crafted from this material.
Day 7 - Free morning in San Gimignano; gelateria visit, cooking class and farewell supper
This morning has been left free to enjoy San Gimignano. You might 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/164 feet, 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 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'll 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'll enjoy our final farewell dinner tonight at the farm, being able to enjoy the fruits of our labours alongside other fare.
Day 8 - Drive to Pisa Airport where the trip ends
Departing San Gimignano this morning, we'll drive to Pisa Galileo Galilei International Airport (PSA) where the tour ends at 8am. The earliest your flight can depart today is 10am.
If you have time to pass before your flight departs, there is luggage storage at the airport and the Pisa Mover rail shuttle will take you into the centre of Pisa in just a few minutes.
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