Wine Trails of Classic Tuscany
Wine Trails of Classic Tuscany
Wine Trails of Classic Tuscany
8 Days Starting in Pisa Airport and ending in Florence
Visiting: Pisa, Castellina in Chianti, San Gimignano, Castelvecchio, Siena, Pienza, Monticchiello, Montepulciano, San Quirico d'Orcia, Metropolitan City of Florence
Tour operator:
Tour code:
LTY
Guide Type:
Fully Guided
Group size:
4 - 16
Physical rating:
Medium, Easy to Moderate
Age range:
16-
Special diets catered:
Vegetarians, Vegans
Tour operated in:
EnglishTrip Styles:
Interests:
Activities:
From:
$2410
$1751 (USD)
Operator discount: -$610
The Big ADVENTURE Sale: -$50
-27%
Tour Overview
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
Highlights
Itinerary
Day 1: Join Trip Pisa Airport; Drive To Castellina In Chianti
Location: Pisa
Accommodation: Guesthouse
Our trip begins at Pisa Galileo Galilei International Airport (PSA) at 5.15 pm. If you would like to join the complimentary airport transfer today, the latest your flight can arrive is 4.45 pm. We will travel together as a group to our guesthouse villa in 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.
If your flight arrives earlier in the day and you wish to venture into Pisa you can leave your luggage at the Information Desk in the Arrivals Area of the terminal. The baggage deposit is open every day between 9am and 7pm and the daily rate for each bag is €7 Euros. The easiset way to reach the city is by the high speed People Mover service which departs from just outside the airport terminal every 5 to 8 minutes and take just a few minutes to reach Pisa Centrale Railway Station. From here it's a 30 minute stroll to Pisa's most famous monument, the Leaning Tower. A taxi should cost no more than €20 Euros.
4
Day 2: Walk In The Heart Of Chianti Country
Location: Castellina in Chianti
Accommodation: Guesthouse
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.
Day 3: Walk To San Gimignano; Wine Tasting
Location: San Gimignano, Castelvecchio, Castellina in Chianti
Accommodation: Guesthouse
This morning we drive towards San Gimignano before setting off on foot 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.
After lunch we plan 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 before driving back to Castellina later this afternoon.
Today's gently undulating ten kilometre walk is expected to take around three-and-a-half hours.
Day 4: Visit Medieval Siena; Drive To Pienza In Southern Tuscany
Location: Siena, Pienza
Accommodation: Hotel
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.
Day 5: Walk To Montepulciano Via Montichiello
Location: Monticchiello, Montepulciano
Accommodation: Hotel
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.
Day 6: Hike In The Val D'orcia To Hill-Top Montalcino
Location: Pienza, San Quirico d'Orcia
Accommodation: Hotel
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.
Day 7: Drive To Florence; Orientation Walk
Location: Metropolitan City of Florence
Accommodation: Hotel
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.
Day 8: Trip Ends In Florence
Location: Metropolitan City of 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.
What's Included
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Fully Guided
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Meals – Breakfast Only
Breakfast: 7
Lunch: 2 -
All Domestic Transportation (including internal flights)
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Accommodation
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Airport Transfers at Destination
What's Not Included
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Tipping and Gratuities
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Country Entry Visas
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1 bottle of Mineral Water per person per day
Check out our Q&As
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What is the maximum group size?
16
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Can you assist with pre or post tour accommodation?
Yes
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Is there any free time to explore places during the tour?
Yes
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Will there be an escort accompanying this tour?
Yes
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Will I know the names and details of all the accommodation before I depart?
Yes
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Are children permitted to take part in the tour?
No
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Are the local guides on the tour English speaking?
Yes
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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.
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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.
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Should I get travel insurance?
Yes–it is a condition of booking that you are fully insured when travelling with us
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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.
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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.
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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
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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.
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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.
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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.
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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.
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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.
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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.
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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
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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.
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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 from Travellers on this Tour
Dates & Availability
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Sunday - Sunday
Apr 21, 2024 - Apr 28, 2024Sunday - Sunday
Apr 28, 2024 - May 05, 2024Sunday - Sunday
May 12, 2024 - May 19, 2024Sunday - Sunday
Sep 08, 2024 - Sep 15, 2024Sunday - Sunday
Sep 15, 2024 - Sep 22, 2024Sunday - Sunday
Oct 06, 2024 - Oct 13, 2024Book with Confidence
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Free Date Changes
Explore! allows you to make 1 free date changes, as long as the change is made at least 60 days before the start of the tour.
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Low Deposit
Explore! requires a minimum deposit of 10% or the full booking value, whichever is less, with the final balance not due until 60 days before departure.
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Cancellation Policy
We don't charge a cancellation fee, here is a summary of explore! charges.
Up to 60 days before tour starts: Forfeit 100% of deposit.
At 59 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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