A Taste of Tuscany - Hilltop Towns and Vineyards

A Taste of Tuscany - Hilltop Towns and Vineyards

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8 Days From

$3050

A Taste of Tuscany - Hilltop Towns and Vineyards

8 Days Starting and ending in Pisa, Province of Pisa, Italy

Visiting: Pisa, Livorno, Montalcino, Buonconvento, Pieve a Salti, Pienza, Siena, Greve in Chianti, San Gimignano, Fattoria Lischeto, Volterra, San Donato

Tour operator:

Explore!

Tour code:

XTY

Guide Type:

Fully Guided

Group size:

10 - 16

Physical rating:

Medium

Age range:

16-99

Special diets catered:

Please Advise Request

Tour operated in:

English

Trip Styles:

Adventure Tours

Activities:

Walking, Wine Tasting

From: $3050

NB: Prices correct on 18-Dec-2024 but subject to change.

This tour is no longer available, please see similar tours below or send an enquiry

Tour Overview

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.

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 agriturismi 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

Itinerary

Expand All

Day 1 : Join Trip In Pisa; Orientation Tour Followed By Welcome Dinner

Location: Pisa

Accommodation: Hotel

Accommodation Name: Bologna

Meals Included: Dinner

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.



If you would like to receive a complimentary airport transfer today, you'll need to arrive into Pisa Galileo Galilei International Airport (PSA). 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

Location: Livorno, Montalcino, Buonconvento

Accommodation: Hotel

Accommodation Name: Albergo Roma

Meals Included: Breakfast, Lunch

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).

Day 3 : Ramble To Agriturismo For Lunch Of Local Organic Produce; Cheese-Tasting In Pienza

Location: Pieve a Salti, Pienza, Siena

Accommodation: Hotel

Accommodation Name: Chiusarelli

Meals Included: Breakfast, Lunch

We'll take in the stunning Tuscan countryside today on a ramble (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.

Day 4 : Guided Walking Tour In Siena: Pasticerria And Pasta Shop Visits

Location: Siena

Accommodation: Hotel, Chiusarelli

Meals Included: Breakfast

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 the Nannini 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). The Nannini family are also coffee roasters. We'll learn about the coffee production process and enjoy a typical Italian brew from beans roasted on the premises.



Later we'll split into smaller groups this afternoon 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

Location: Greve in Chianti, San Gimignano

Accommodation: Hotel

Accommodation Name: La Cisterna

Meals Included: Breakfast

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.

Day 6 : Farm Tour And Lunch At An Agriturismo; Visit To Medieval Volterra

Location: Fattoria Lischeto, Volterra

Accommodation: Hotel

Accommodation Name: La Cisterna

Meals Included: Breakfast, Lunch

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.

Day 7 : Free Morning In San Gimignano; Gelateria Visit, Cooking Class And Farewell Supper

Location: San Gimignano, San Donato

Accommodation: Hotel

Accommodation Name: La Cisterna

Meals Included: Breakfast, Dinner

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.

Day 8 : Drive To Pisa Airport Where The Trip Ends

Location: San Gimignano, Pisa

Meals Included: Breakfast

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.

What's Included

  • Accommodation

    7 nights comfortable hotel.

  • Fully Guided

    The tour includes fully guided tours to enhance your experience.

  • Airport Transfers at Destination

    Complimentary airport transfer to and from Pisa Galileo Galilei International Airport (PSA) on the first and last day of the tour.

  • Meals

    Meals are provided as per the itinerary.

What's Not Included

  • International Travel

  • Optional Activities

Meals

Breakfasts: 7
Lunches: 3
Dinners: 2

Check out our Q&As

  • What is the standard of the hotels on this tour?

    7 nights comfortable hotel.

  • What is the fitness level required to do this tour?

    Modrate

  • Is there any free time to explore places during the tour?

    As per details given in an itinerary.

  • Are children permitted to take part in the tour?

    Yes, minimum age 16 years or above.

  • What is the maximum group size?

    16

  • Are airport transfers included in this tour?

    Yes, complimentary airport transfer is provided on the first and last day of tour.

  • Are flights included in this tour?

    International flights are not included however domestic flights are included

  • Are the local guides on the tour English speaking?

    Yes, English speaking tour guide on this tour.

  • I'm going on a walking/cycling trip-do I need to train?

    It will depend on the grade and how fit you already are. Check the trip page for details of the walking or cycling grade and how far you’ll be walking/cycling each day. For moderate or challenging trips in particular we’d recommend doing some walks or cycles before you leave to build up your fitness and prepare you for the distances being covered.

  • Who will be my travelling companions on the tour?

    We have a wide range of ages nationalities on our small group trips and they come from all walks of life.

  • Should I get travel insurance?

    Yes–it is a condition of booking that you are fully insured when travelling with us

  • How long has the tour company been trading?

    At Explore, we're the experts in adventure travel. Our small group adventure holidays have been running since 1981. Today, Explore is one of the most trusted travel companies in the UK with over 500 trips to more than 120 countries.

  • Can I join the tour once it has departed?

    Yes, but there are no concessions for doing so, and we must have a record in your booking advising as such before the trip departs.

  • Am I contributing to any charity by booking the tour?

    Being a responsible company is a large statement, something that has to be entwined within the very fibre of a company. Discover the charities and partnerships we support as part of this at https://www.explore.co.uk/about/sustainability/charities-and-partners

  • What happens if I need to change my holiday date once I’ve booked?

    We want to be as clear as and as honest as possible about what happens if you decide to that you no longer wish to travel on your trip. Our booking conditions have details of the costs you’ll incur when you cancel-these charges depend on how long it is before your planned departure.

  • What is the accommodation like?

    We choose comfortable accommodation in the best locations possible. We opt for small, local and family-run accommodation where we can, as opposed to large chain hotels. We typically use hotels that are the equivalent of European 3-star, and you’ll usually have an en suite room. Occasionally, where we want to get off the beaten trail we may stay in more basic accommodation.

  • What Ethical Travel credentials does the tour company have?

    Sustainability is embedded within the fibre of Explore, it emanates from the inside out. But as we enter a new decade it is clearer than ever that our world needs help, and Explore has created a sustainability strategy based on the 2015 UN’s Sustainable Development Goals.

  • What policies are in place for Covid-19?

    Our flexible booking and safety policies mean you're protected before and during your travels with us. Receive a full refund if your trip is cancelled, transfer your trip free of charge up to 10 days before departure minus any irrocoverable costs.

  • Do I need to be very fit to book with you?

    All our trips require some level of active participation. This could be on a cultural trip, trek, safari, expedition or voyage. It is in the interests of all members of the group that everyone should be capable of fully participating in the activities of their chosen trip.

  • What documents will I receive before I travel?

    Final documents will include a comprehensive trip itinerary, climate and country information, budgeting and packing advice visa and passport information and details on optional activities available.

  • Do you operate a “single share” option and how does it work?

    Yes on most of our trips. Most trips are based on customers sharing twin-bedded rooms. If you book a group trip as an individual, you will share a room with someone of the same sex. However, on many trips we offer the opportunity to pay a supplement to pre-book a single room, known as our single room option. On some trips a single room will be provided every night, on others it will be provided o

  • Do we have to be vaccinated against Covid-19 to travel

    It’s now a condition of booking a trip with us that customers should have one of the following before they travel - — Be vaccinated against COVID, having received the full recommended course, and allowing enough time for immunity to take effect. Full vaccination includes any booster required to keep the vaccine valid. — Have taken a negative test (rapid antigen or PCR) within 72hrs of departure.

  • Will the accommodation included meet local health and safety regulations?

    Explore will only offer hotels that have specific COVID-19 protocols in place and comply with local government guidelines. We will ensure these measures include; enhanced room cleaning, ventilation, social distancing, regular cleaning and disinfection of high frequency touch points in public areas, food safety, staff re-training and minimising contact within the properties.

Reviews of this operator

Feefo Rated Customer  

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02-Nov-2021

' Excellent trip with a mixture of easy riding days, mixed with great scenary ' The trip was excellently organised by the group leader. The accommodation was very good throughout the trip. The bikes were ideal for this trip.

Gemma Jackson  

Peru Encompassed - spectacular trip

02-Jan-2023

I booked for my husband and I to go on the Peru Encompassed trip with the 3 day Amazon extension trip tagged on the end, we also booked to go to Lima few days early to get over the jetlag and see something of Lima before setting off on the group trip. Everything was booked for us by Explore! with seamless ease and without any hitches. This was the first time I had booked onto an organised trip so I was a bit concerned it might not be for us. How wrong I was. We were a group of 9, ranging from 30s to 60s, and a mixture of couples and singles and different nationalities. As a group we gelled really well and chose to spend most of our free time together which made the trip great fun. As for the trip itself, it surpassed all expectations. The Peru Encompassed trip was superb. I don't think any other country offers so much culture, wildlife, specular scenery and amazing food, all of which we experienced in abundance on the trip. We had a local tour guide for the whole trip who was fantastic and then expert guides joined us on different legs of the journey. We learned so much as a result. The highlights for me were visiting the local market in Arequipa with our guide and sampling lots of different fruit and street foods, the day on Lake Titicaca and of course Machu Picchu itself. We booked an additional trip to go back ourselves the second morning which was great as we could do a different route around the ruins and get different views from the afternoon before. Our final highlight was the additional 3 day trip to the Amazon staying at the Hacienda Conception. The lodges were immersed in the jungle which was wonderful if noisy! the food was fab and the daily trips provided were excellent. It was a great relaxing way to end the trip although it did rain quite a bit. Both my husband and I said our trip to Peru was one of the best trips we have ever done.

Trustpilot
Ms D Brown  

Excellent company

07-Dec-2022

Excellent company, there are so many trips, you really get looked after. Everything is dealt with by your Tour Leader, all logistics are taken care of and usually things go smoothly, I only use explore because I know what to expect each time, that makes me happy, with a stress free holiday

Trustpilot
Stephen  

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08-Nov-2021

Very well organised tour. Brilliant Tour Leader who went out of her way to make sure everyone was happy and enjoyed the trip. The Azores are an incredible location with amazing scenery and good food.

Barbara in Beckenham  

Iceland Northern Lights Adventure

05-Nov-2021

' Steina was a great guide - full of information made the trip so interesting ' Everything was just perfect - just as I had hoped - except the Northern lights were a no show!

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May 04, 2025 - May 11, 2025
$3460

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May 18, 2025 - May 25, 2025
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Jun 15, 2025 - Jun 22, 2025
$3050

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Jul 20, 2025 - Jul 27, 2025
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Sep 14, 2025 - Sep 21, 2025
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Sep 28, 2025 - Oct 05, 2025
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Oct 12, 2025 - Oct 19, 2025
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Book with Confidence

  • Free Date Changes

    Explore! allows you to make 1 free date changes, as long as the change is made at least 70 days before the start of the tour.

  • Low Deposit

    Explore! requires a minimum deposit of 10% or the full booking value, whichever is less, with the final balance not due until 70 days before departure.

  • Cancellation Policy

    We don't charge a cancellation fee, here is a summary of explore! charges.

    Up to 70 days before tour starts: Forfeit 100% of deposit.

    At 69 days before tour starts: Forfeit 30% of booking price.

    At 41 days before tour starts: Forfeit 60% of booking price.

    At 27 days before tour starts: Forfeit 90% of booking price.

    At 13 days before tour starts: Forfeit 100% of booking price.

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