Bookmundi
Check Availability

Wine Trails Of Classic Tuscany

  • No booking or credit card fees
days 08 US$ 1,390 US$ 1,320
SavingUS$ 70
highlights
  • Tuscan landscapes - Walks amongst vineyards, rolling fields and avenues of cypress trees
  • Wine tastings - Sample some of Italy's finest wines from Chianti to Brunello
  • Hill-top towns - Discover San Gimignano, Pienza, Montepulciano and Montalcino
  • Siena and Florence - Explore these stunning medieval and renaissance cities
The Wine Trails of Classic Tuscany tour starts in Pisa Airport and ends in Florence. The Wine Trails of Classic Tuscany is a Wine Tasting Tour that takes 8 days taking you from Pisa Airport to Florence and through other destinations in Italy.

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
Select Tour Version:
Joining the trip in Pisa today, we drive to our hotel 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.
Accommodation
  • Standard 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. On our way back to Castellina we will stop at the Rocca della Macie wine estate for a tour and tasting of the famous Chianti Classico.

Today's seven kilometre walk is expected to take around four hours with a total ascent and descent of 150 metres.
Meals
  • Breakfast & Lunch
Accommodation
  • Standard 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.
Meals
  • Breakfast
Accommodation
  • Standard guesthouse
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.
Meals
  • Breakfast
Accommodation
  • Standard 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.
Meals
  • Breakfast
Accommodation
  • Standard 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.
Meals
  • Breakfast & Lunch
Accommodation
  • Standard 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.
Meals
  • Breakfast
Accommodation
  • Standard hotel
The trip ends this morning after breakfast in Florence. If you are flying from Pisa Airport today, Explore will organise for your transfer direct to the airport by public shuttle bus with a journey time of around 70 minutes.
Meals
  • Breakfast
what’s included
Meals
  • 7 Breakfast, 2 Lunch
Accommodation
  • 3 nights standard guesthouse
  • 4 nights standard hotel
Transport
  • Minibus, Train
Guide
  • Explore Tour Leader / Trek Guide
what’s excluded
  • International Flights
  • Any international flights to Pisa Airport and from Florence are not included in this price. We always recommend that you arrive 1 day prior to your tour starting date.
  • Travel Insurance
  • Travel insurance is not included in this Wine Trails of Classic Tuscany tour. Travel insurance is mandatory to buy. We recommend purchasing it from World Nomads.
Tour details
Duration 8 days
Tour Type Group Tour - Max 17 participants
guiding method Live guide/instructor
Guide Language English
Starts/Ends Pisa Airport, Italy/ Florence, Italy
Get a PDF file with detailed trip information: Download Trip Notes for Wine Trails of Classic Tuscany
Availability
  • Best price guaranteed
Select Departure Month:
Filter Departures:
  • {{data.start_date | inDate }} from
  • {{data.finish_date | inDate}} in
  • Only {{(data.seats > 10 ?'10+':data.seats)}} seat{{data.seats >1?'s':''}} left Sold Out
  • From {{symbol}} {{sepNum(data.original_price)}} {{symbol}} {{sepNum(data.discounted_price)}} Saving {{symbol}} {{sepNum(data.discount_amount)}} + US$ {{priceSeperator(data.local_payment)}} Local Payment + {{data.local_payment_currency}} {{priceSeperator(data.local_payment_amount)}} Local Payment
{{data.booking_type}} -{{data.discount}}%
Monthly Price Comparision
Why Book with Bookmundi
  • Bookmundi is partner with Explore. You're seeing real-time prices and availabilities.
  • Save US$ 70 when booking on Bookmundi.
  • Save +US$ 46 in Travel Credits on your next booking.
  • Best Price Guaranteed.
  • No Credit Card or Booking fees.
  • +25,000 customer reviews, with an average rating of 4.9 of 5.0 possible.
  • 100% Financial protection. Bookmundi is member of the Danish Travel Fund which guarantees for any payment made via us. Your money is safe.
What are customers saying about Bookmundi
Good to know
Payment

A deposit of 132 USD is required to confirm this tour. The remaining balance will be charged 59 days before departure. For any departures within 24 August 2019 full payment is required.

Travel Insurance

The Wine Trails of Classic Tuscany tour requires that you have adequate and valid travel insurance covering medical and personal accidents, including repatriation costs and emergency evacuation. We recommend using World Nomads' travel insurance.

Visa

For this Wine Trails of Classic Tuscany tour getting the required visa(s) is the responsibility for each individual traveller, as visa requirements vary depending on your nationality. We recommend to check with your local embassies representing the countries that you are travelling to, as part of this itinerary.

CancellationNo additional cancellation fees apply for this Wine Trails of Classic Tuscany tour. You can cancel the tour up to 60 days prior departure and avoid paying the full amount, but your deposit paid is non-refundable. No refund applies for cancellations within 59 days of departure.
person
{{agReviews.ratings.rating}} - {{agReviews.ratings.rating>4.5?'Excellent':agReviews.ratings.rating>3.5?'Very Good':agReviews.ratings.rating>2.5?'Average':agReviews.ratings.rating>1.5?'Poor':'Very poor'}}
For
From {{review.country}} At {{review.edit_date?review.edit_date:review.add_date | date:'mediumDate'}}
“ {{review.total_score>4.5?'Excellent':review.total_score>3.5?'Very Good':review.total_score>2.5?'Average':review.total_score>1.5?'Poor':'Very poor'}} ” “ {{review.product_score>4.5?'Excellent':review.product_score>3.5?'Very Good':review.product_score>2.5?'Average':review.product_score>1.5?'Poor':'Very poor'}}”
{{agency.name + ' responded to this review on '}} {{review.product_review_response_date | date:'mediumDate'}}
Back to top
image description
{{(chatView=='product' || chatView=='viewoffers')?activeuser:getFirstName(activeuser)}}
{{productTitle}}
{{productTitle}} {{productTitle}}
View Offer

Hello! from, {{activeuser}}

Replies will be sent directly to your email address, if offline.

  • Confused?
  • Queries?
  • Or just feeling alone?

Communicate with {{getFirstName(activeuser)}}

  • Replies will be sent to your own email address, from where you can continue the conversation.
  • 1. Your enquiry is sent directly to the company.
  • 2. They will reply to your own email, from where you can continue the conversation.

Communicate with Communicate with {{activeuser}}

  • 1. Your enquiry is sent directly to the company.
  • 2. They will reply to your own email, from where you can continue the conversation.
{{stickyMessage}}
No conversations yet :(
Hi ,
Thanks for your trip input. We will do our utmost to make sure that you get a trip of a lifetime.
We've noted down your trip requirements below. You can easily them.
  • {{myRequest.title}}
  • Country: {{!!tripPlannerKeysNames[myRequest.id].geoLocation?tripPlannerKeysNames[myRequest.id].geoLocation:myRequest.country}}
  • Destination: {{tripPlannerKeysNames[myRequest.id].destinations.join(', ')}}
  • Activity: {{tripPlannerKeysNames[myRequest.id].activity.join(', ')}}
  • Custom Destination: {{tripPlannerCustom[myRequest.id].destination}}
  • Custom Activity: {{tripPlannerCustom[myRequest.id].activity}}
  • Group Size: {{myRequest.no_of_adults > 0 && myRequest.no_of_children > 0?',':''}} {{myRequest.group_type=='Single'?'1 Person':myRequest.group_type=='Couple'?'2 People':''}}
  • {{myRequest.departure_month || myRequest.duration?'Approx. Dates':'Travel Dates'}}: {{myRequest.start_date | readableDate}} to {{myRequest.end_date | readableDate}} {{myRequest.departure_month}}, {{myRequest.duration}} Not decided yet
  • Tour Type: {{myRequest.tourtype | tourtypefullName}}
  • Age Group: {{myRequest.age_group}} yrs
  • Type of Tour: {{tripPlannerKeysNames[myRequest.id].type_of_tour}}
  • Accommodation Option: {{tripPlannerKeysNames[myRequest.id].accommodation_option}}
  • Budget Per Person: USD {{myRequest.approx_budget_amount}}
  • Budget Flexibility {{tripPlannerKeysNames[myRequest.id].budget_flexibility}}
  • Trip Planning Stage {{myRequest.trip_planning_stage}}
  • Trip Details: ... Read More Read Less
How our Travel Expert Service Works
  • 1 We connect you with a hand-picked and qualified travel expert who can match your trip requirements. The advantage of working directly through a travel expert is that you get the best and unfiltered advice from the very beginning.
  • 2 The travel expert will help you with creating and customising a trip for you. If you have any questions or concerns relating to the trip, the travel expert will also be able to help you with those.
  • 3 When you feel that your trip is exactly per your wish, you'll be able to book the entire trip here on Bookmundi.
The Advantages of Bookmundi
  • Selected Local Travel Experts All our local travel experts have been chosen based on rigorous selection criteria. In fact, we reject 98 out of 100 local travel agencies, and thereby giving you access to the top 1-2% local travel experts.
  • Secure Online Payment and Financial Guarantee Each and every trip is required to go through Bookmundi's secure payment platform, powered by Stripe and supported by SSL. All payments are therefore carried out in secure manners. We are furthermore member of the Danish Travel Fund which gives you a 100% financial guarantee for any money you pay on Bookmundi, even if we went bankrupt (which we we will not!).
  • Trip Replacement or 100% Reimbursement Bookmundi has hand-picked your local travel expert. Our role, as your trusted third party, is therefore to make sure that your entire experience runs as seamless and secure as possible. We guarantee to you that in the unlikely event where a local travel expert cancels your trip after your deposit or full payment has been made, we commit to replacing these services with another equally qualified agency so that your trip can go ahead as planned, or failing to replace it, we will give you a 100% reimbursement.
New customised trip enquiry by {{getFirstName(activeuser)}}:
  • Title: {{myRequest.title}}
  • Country: {{!!tripPlannerKeysNames[myRequest.id].geoLocation?tripPlannerKeysNames[myRequest.id].geoLocation:myRequest.country}}
  • Destination: {{tripPlannerKeysNames[myRequest.id].destinations.join(', ')}}
  • Activity: {{tripPlannerKeysNames[myRequest.id].activity.join(', ')}}
  • Custom Destination: {{tripPlannerCustom[myRequest.id].destination}}
  • Custom Activity: {{tripPlannerCustom[myRequest.id].activity}}
  • Group Size: {{myRequest.no_of_adults > 0 && myRequest.no_of_children > 0?',':''}} {{myRequest.group_type=='Single'?'1 Person':myRequest.group_type=='Couple'?'2 People':''}}
  • {{myRequest.departure_month || myRequest.duration?'Approx. Dates':'Travel Dates'}}: {{myRequest.start_date | readableDate}} to {{myRequest.end_date | readableDate}} {{myRequest.departure_month}}, {{myRequest.duration}} Not decided yet
  • Tour Type: {{myRequest.tourtype | tourtypefullName}}
  • Age Group: {{myRequest.age_group}} yrs
  • Type of Tour: {{tripPlannerKeysNames[myRequest.id].type_of_tour}}
  • Accommodation Option: {{tripPlannerKeysNames[myRequest.id].accommodation_option}}
  • Budget Per Person: USD {{myRequest.approx_budget_amount}}
  • Budget Flexibility {{tripPlannerKeysNames[myRequest.id].budget_flexibility}}
  • Trip Planning Stage {{myRequest.trip_planning_stage}}
""
Can you handle {{getFirstName(activeuser)}}'s enquiry? Rejection Reason
{{myRequest.reject_reason?myRequest.reject_reason:'Sorry, Your trip request has been rejected.'}}
img description img description img description
seen

{{(duplex.offer_mode==1 && messages.length==1 && iamagency==1)?'Messaging this user is blocked momentarily':settings.bolcked_message}}
{{qResponse.message}}
Guideline for Responding to Customised Trip Requests
Dear {{!activeuserExpert ? activeuserExpert.first_name: 'N/A'}}, Before responding to {{getFirstName(activeuser)}}’s customised trip request for {{plannerCountries}} we recommend that you carefully read these guidelines as they will help you with approaching the customer correctly and convert the enquiry into a trip booking.
{{errorMessage}} Okay, got it! Need help?Contact us
This message will be delivered as an email because {{getFirstName(activeuser)}} is currently offline.
  • {{files.file_name}}
Hi ,
Thanks for your trip input. We will do our utmost to make sure that you get a trip of a lifetime.
We've noted down your trip requirements below. You can easily them.
  • {{myRequest.title}}
  • Country: {{!!tripPlannerKeysNames[myRequest.id].geoLocation?tripPlannerKeysNames[myRequest.id].geoLocation:myRequest.country}}
  • Destination: {{tripPlannerKeysNames[myRequest.id].destinations.join(', ')}}
  • Activity: {{tripPlannerKeysNames[myRequest.id].activity.join(', ')}}
  • Custom Destination: {{tripPlannerCustom[myRequest.id].destination}}
  • Custom Activity: {{tripPlannerCustom[myRequest.id].activity}}
  • Group Size: {{myRequest.no_of_adults > 0 && myRequest.no_of_children > 0?',':''}} {{myRequest.group_type=='Single'?'1 Person':myRequest.group_type=='Couple'?'2 People':''}}
  • {{myRequest.departure_month || myRequest.duration?'Approx. Dates':'Travel Dates'}}: {{myRequest.start_date | readableDate}} to {{myRequest.end_date | readableDate}} {{myRequest.departure_month}}, {{myRequest.duration}} Not decided yet
  • Tour Type: {{myRequest.tourtype | tourtypefullName}}
  • Age Group: {{myRequest.age_group}} yrs
  • Type of Tour: {{tripPlannerKeysNames[myRequest.id].type_of_tour}}
  • Accommodation Option: {{tripPlannerKeysNames[myRequest.id].accommodation_option}}
  • Budget Per Person: USD {{myRequest.approx_budget_amount}}
  • Budget Flexibility {{tripPlannerKeysNames[myRequest.id].budget_flexibility}}
  • Trip Planning Stage {{myRequest.trip_planning_stage}}
  • Trip Details: ... Read More Read Less
How our Travel Expert Service Works
  • 1 We connect you with a hand-picked and qualified travel expert who can match your trip requirements. The advantage of working directly through a travel expert is that you get the best and unfiltered advice from the very beginning.
  • 2 The travel expert will help you with creating and customising a trip for you. If you have any questions or concerns relating to the trip, the travel expert will also be able to help you with those.
  • 3 When you feel that your trip is exactly per your wish, you'll be able to book the entire trip here on Bookmundi.
The Advantages of Bookmundi
  • Selected Local Travel Experts All our local travel experts have been chosen based on rigorous selection criteria. In fact, we reject 98 out of 100 local travel agencies, and thereby giving you access to the top 1-2% local travel experts.
  • Secure Online Payment and Financial Guarantee Each and every trip is required to go through Bookmundi's secure payment platform, powered by Stripe and supported by SSL. All payments are therefore carried out in secure manners. We are furthermore member of the Danish Travel Fund which gives you a 100% financial guarantee for any money you pay on Bookmundi, even if we went bankrupt (which we we will not!).
  • Trip Replacement or 100% Reimbursement Bookmundi has hand-picked your local travel expert. Our role, as your trusted third party, is therefore to make sure that your entire experience runs as seamless and secure as possible. We guarantee to you that in the unlikely event where a local travel expert cancels your trip after your deposit or full payment has been made, we commit to replacing these services with another equally qualified agency so that your trip can go ahead as planned, or failing to replace it, we will give you a 100% reimbursement.
New customised trip enquiry by {{getFirstName(activeuser)}}:
  • Title: {{myRequest.title}}
  • Country: {{!!tripPlannerKeysNames[myRequest.id].geoLocation?tripPlannerKeysNames[myRequest.id].geoLocation:myRequest.country}}
  • Destination: {{tripPlannerKeysNames[myRequest.id].destinations.join(', ')}}
  • Activity: {{tripPlannerKeysNames[myRequest.id].activity.join(', ')}}
  • Custom Destination: {{tripPlannerCustom[myRequest.id].destination}}
  • Custom Activity: {{tripPlannerCustom[myRequest.id].activity}}
  • Group Size: {{myRequest.no_of_adults > 0 && myRequest.no_of_children > 0?',':''}} {{myRequest.group_type=='Single'?'1 Person':myRequest.group_type=='Couple'?'2 People':''}}
  • {{myRequest.departure_month || myRequest.duration?'Approx. Dates':'Travel Dates'}}: {{myRequest.start_date | readableDate}} to {{myRequest.end_date | readableDate}} {{myRequest.departure_month}}, {{myRequest.duration}} Not decided yet
  • Tour Type: {{myRequest.tourtype | tourtypefullName}}
  • Age Group: {{myRequest.age_group}} yrs
  • Type of Tour: {{tripPlannerKeysNames[myRequest.id].type_of_tour}}
  • Accommodation Option: {{tripPlannerKeysNames[myRequest.id].accommodation_option}}
  • Budget Per Person: USD {{myRequest.approx_budget_amount}}
  • Budget Flexibility {{tripPlannerKeysNames[myRequest.id].budget_flexibility}}
  • Trip Planning Stage {{myRequest.trip_planning_stage}}
""
Can you handle {{getFirstName(activeuser)}}'s enquiry? Rejection Reason
{{myRequest.reject_reason?myRequest.reject_reason:'Sorry, Your trip request has been rejected.'}}
Looking for available travel experts
No conversations yet :(