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Tuscany Hike –  Volterra, Siena & Chianti

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Tuscany Hike –  Volterra, Siena & Chianti Write a review

  • Location: Italy
  • Duration: 7 days/6 nights
  • Departing from: Florence 9:00 a.m. on Sunday, Day 1
  • Tour finishes: Florence train station, 11:00 a.m. on Saturday Day 7
  • Departures 2024: April 21, May 5 & 19, Sept 15, Oct 13, plus private departures.
  • Price 2024: Euro €3,250 per person in double occupancy. Single supplement Euro €450. One guide accompanies departures of 2 - 8 people, two guides for 9 or more.

Discover the mysterious Etruscan civilization of Volterra, see the stunning medieval towers of San Gimignano, explore the labyrinth of ancient Colle di Val d’Elsa, and admire Siena’s splendid “Il Campo” square, arguably the most beautiful in all of Italy. Combine the sensual pleasures of Tuscany’s sublime cuisine, delicious wine, and Mediterranean sunshine with the physical pleasure of an active holiday hiking through some of the most beautiful countryside in the world. [Read an article about our Tuscany Hike that appeared in New Zealand’s “Otago Daily Times” written by deputy editor Simon Cunliffe. Click here.]

Tuscany Hike – Volterra, Siena & Chianti Hiking Tour Includes

  • Accommodation: 6 nights accommodation in 4 star hotels (2 nights Volterra at La Locanda, 2 nights Colle di Val d’Elsa at Palazzo San Lorenzo, 2 nights Radda in Chianti at Palazzo Leopoldo.)
  • Meals: 6 breakfasts, Pic-nic lunch, Cesani Winery lunch, Croce di Bibbiano winery lunch, 5 dinners
  • Luggage: Bags are transfered from pick-up in Florence on Day 1 until drop-off at the Florence train station at the end of the tour
  • Special events: Guided visits of Siena, Volterra, entrance to Etruscan museum in Volterra, and two winery wine-pairing/tasting lunches
  • Transport: Private van transfers as indicated in the itinerary
  • Active days: 6 days of guided hiking
  • Guides: At least 1 bilingual Customwalks guide accompanies departures of 2 - 8 people; & 2 guides accompany departures of 9 or more people
  • Max group size: Tours are capped at 14 people

 

Booking: Please e-mail us at info@customwalks.com to receive a booking contract or simply click on the BOOK NOW button or the 'Contact Us' tab. Thanks!

Tuscany Hike –  Volterra, Siena & Chianti itinerary Request full itinerary

Day 1 – Pick up Florence, Volterra

Our trip begins in Florence, Italy. The group will meet at centrally-located hotel this morning, load luggage into the support vehicle and transfer to the outskirts of Volterra. We begin our first hike to this historic Tuscan town, situated on a plateau overlooking the surrounding countryside. Our hike takes us up through olive groves and vineyards, past stone farmhouses, and eventually to the imposing city walls. We have a light lunch in a local trattoria followed by a guided hiking tour of Volterra, whose history spans Etruscan, Roman, Medieval and Renaissance periods. We visit the Etruscan Museum, where 3,000-year-old sculpted funerary urns, ceramics, and filigreed gold jewelry bear witness to the extraordinary sophistication of the Etruscan civilization. From atop the city's medieval walls we look down on the Roman Theater and out across the landscape of western Tuscany to the sea. On a clear day you can even see the islands of Elba and Corsica. The rest of the afternoon is free until we meet for an aperitivo and a brief orientation, followed by dinner. Overnight in Volterra at the four-star hotel La Locanda for the next two nights. Hiking: 6 kms/4 miles; Elevation gain: 220 m/70 ft. Duration: 2 hrs Driving: 1.5 hours. Hotel, lunch and dinner included. Hiking: 

Day 2

Following breakfast, we transfer into the countryside to begin our hike through oak forests and vast wheat fields, surrounded by cypress trees and stone farmhouses. At the hamlet of Ulignano we stop for a picnic lunch at a farmhouse. Continuing our hike, we'll see Volterra's towers and steeples across the valley. After a van shuttle back to our hotel, the afternoon is free to explore Volterra or relax before dinner. Hiking: 12 kms/ 7.5 mile; Elevation gain: 270 m/ 800 ft.  Duration: 3 hrs Driving: 20 minutes each way. Hotel, breakfast and dinner included.

Day 3

After breakfast a thirty-minute transfer to Certaldo, to hike a route that affords us wonderful views of the "city of the towers," San Gimignano, and the imposing mass of the Villa Monte in the distance. We stop at Cesani, a small family-run winery which produces excellent Chianti and Vernaccia. A short tour is followed by a home-cooked lunch in which each course is paired with one of their wines. From here we transfer to San Gimignano to explore this exquisite medieval village. We finish the day in Colle di Val d'Elsa, an authentic Tuscan hilltown whose historic center still thrums with the rhythms of everyday life and is home to Italy's finest crystal makers. We spend the next two nights in Colle in the four-star Palazzo San Lorenzo. Hiking:12 kms/ 7.5 miles Elevation gain: 260 m/ 780 ft. Duration: 3 hrs. Driving:thirty minutes each way. Hotel and all meals included.

Day 4

A scenic loop hike from Colle takes brings us to a country residence set alongside the Via Francigena, which connects San Gimignano to Colle. We enjoy the wonderful views of the Tuscan hills and San Gimignano's distant towers while eating lunch on the terrace. Continuing on our hike we arrive back into Colle, with the afternoon free to peruse the crystal shops and a museum which highlights the centuries long tradition of crystal making in Colle di Val d'Elsa. Dinner is on your own, providing the opportunity to choose from a variety of authentic local trattorias and restaurants. Hiking: Hiking: 15 kms/ 9.5 miles; Elevation gain: 155 m/ 500 ft. Duration: 4 hrs Hotel, breakfast and lunch included.

Day 5

We transfer to beautiful Siena, one of Italy's most enchanting cities. Conquered by the Medicis in 1559, Siena became a backwater, frozen in time, making it one of Europe's finest examples of a preserved Gothic city. The high concentration of buildings from the 12th–14th centuries make Siena unique, and the main square, "Il Campo," is considered by many to be Italy's most beautiful piazza (the famous bareback "Palio" horserace is held in the square twice each year). Our local guide will explain the mayhem and passion associated with the race and then take us to visit the Duomo and its medieval treasures. You'll have the rest of the afternoon to explore Siena on your own. Wander through its sinuous medieval streets, discover hidden piazzas, or simply relax with a glass of wine before we transfer to our four-star Palazzo Leopoldo, a Tuscan villa hotel in the hilltop town of Radda in Chianti. We spend the next two nights in this historic and charming walled village. Hotel, breakfast and dinner included. Driving: 35 minutes in the morning, and 45 minutes in the afternoon.

Day 6

Today's hike starts as you step out of the hotel. Exit Radda and you are soon amongst vineyards and olive groves. We pass the winery of Colle Berreto and climb up to a ridge line for views back on to Radda and over the surrounding countryside. The trail leads us along a cypress lined driveway to the magnificent Villa Vistarenni whose fanciful facade is a Chianti landmark. We have a break beneath the villas original 16th century walls before continuing on to the walled medieval hamlet of Vertine. We are rewarded with vast views over the undulating hills of Chianti from Vertine's perched vantage point. We have lunch at a charming osteria in the village of Gaiole in Chianti, famous for its Chianti wines but also as home to the "Eroica" bike race. After lunch we return to Radda in Chianti with a private shuttle, where the remainder of the afternoon is free to swim in the pool, explore the town's medieval center, or rest. We enjoy a final dinner together to celebrate our time in Tuscany. Hiking: 11.5 kms/ 7 miles; Elevation gain: 360 m / 1,150 ft'.​ Duration: 3 hrs. Hotel, breakfast and dinner included.

Day 7

After breakfast we shuttle everyone to the Florence train station, arriving around 11:00 am. From there you can easily catch trains for the rest of Italy. Travel time to both Rome and Milan is about 1 hour and forty minutes. Breakfast and one group transfer included.

Please note: Some details of the itinerary may change according to the departure date of your tour. Whenever we run a tour we make new discoveries. Sometimes they are good discoveries, like a wonderful new trattoria, and sometimes they are bad, like a trail has been washed away. The result is that we sometimes change our itinerary to improve it by adding new wonderful elements to the tour or by removing something that does not work anymore. Rest assured, our goal is to always provide you with the best possible experience. We will advise you of any changes to the original itinerary prior to departure.  

The Hikes

The hikes in Tuscany cover a variety of terrain, from trail to dirt road, with many rolling hills to climb or descend. We have designed the trip so that there is always some free time in the late afternoon so you can relax, read, or enjoy the towns where we stay. Breakfast is included every day, and dinners reflect the excellent traditional food of the region. Daily distance between 8 and 16 kms (5 to 10 miles).

Activity Level 3 out of 5 = Moderate:
In general: This is a Moderate tour for fit hikers, and a little challenging but do-able for not-so-fit hikers.
Terrain: Rolling to hilly terrain with frequent climbs and descents, often over rocky terrain. May have some short, relatively steep climbs and descents. 
Actual hiking time: between 2-5 hours per day, mostly in the morning but also in the afternoon.
Distances: Usually between 8 and 12 kms/5 and 7 miles. Max distance is 14 kms/8 miles.
Surfaces: Trails consisting of mostly compact earth, gravelly earth, and sometimes dirt-gravel roads and on occasion rocky and uneven trails. 
Footing: Good, but on occasion you have to pay attention to where and how you place your feet. Proper hiking shoes with thick soles with good treads are required. Sport sandals, running shoes and tennis shoes are not adequate.
Specifics: Tuscany is hilly, so expect a lot of rolling and sometimes steep uphills and downs.
Hiking Poles: Recommended but not required, but if you habitually use hiking poles then you will find them helpful.  
Compared to the Cinque Terre: These tours are easier than the hikes in the Cinque Terre.
Other: This tour is appropriate for fit first time “hikers” who enjoy hiking and who have good balance and who are coordinated. 
Moderate Tours: Tuscany Chianti, Dordogne Hike, Sicily Hike, Lake Como Hike, and Corsica.
As a point of reference, what is a 1 out of 5 Activity rating? A 1 out of 5 rated tour is a tour without any hiking. Hikes would be in towns, cities, and villages, and the countryside hikes would be on paved, or gravel/dirt roads, and occasionally on some packed earth trails. Elevation gain and loss would be negligible.
As a point of reference, what is a 5 out of 5 Activity rating? A 5 out of 5 rated tour is a tour that would be physically challenging and technically difficult even for very fit and experienced hikers. The hikes would have steep ascents and descents on narrow, exposed trails with challenging footing, such as on scree fields, or through rock falls and boulders. Distances would be up to 25 km/16 miles per day and feature ascents of over 1,000 m/3,200 feet in a day. A 5 out of 5 tour would also mean that you would be carrying a heavier-than-normal pack. None of our tours are rated 5 out 5. Our most challenging tours are 4.5 out of 5, and they are the Dolomites Alta Via (because of some exposed trail that requires some technical expertise) and our Republic of Georgia tour which has some long hikes with over 1,000 meters of elevation gain.

Getting There: the trip starts at noon in Florence on Sunday. Florence is well connected by road, rail and air with the rest of Italy and Europe. 

Air: Florence airport receives both domestic and international flights, through European hubs such as London, Paris, Frankfurt, Amsterdam, Munich and Brussels. You can also fly into Pisa (about an hour away by train) on many low-cost airlines. For a complete list of Italian airports and a selection of low-cost airlines, see our "Transport Info" page.

Rail: The Eurostar and new Italo high-speed trains connect Florence with Milan (travel time about 2.5 hours), Bologna (travel time 35 mins) and Rome (travel time 1.5 hrs). See the Trenitalia website (in English) at this link. For alternative high-speed rail travel, see the Italo website. For complete information on using the Italian train system, see our blog post.

Road: The A1 Autostrada connects Florence with the rest of Italy. Travel time from Milan is about 5 hours, from Bologna 1.5 hours, and from Rome about 3 hours.

Getting Away at the End of the Trip: the trip ends after breakfast on Saturday morning with a transfer to the Florence train station. Trains from Florence to Rome, Milan, Venice, Pisa, etc. leave every hour.

If you book a trip with us you will receive detailed information about how to get to and from the trip, and of course you can e-mail us with any questions.

5/5
RatingRatingRatingRatingRating  
5 out of 5
Ratings based on 11 Verified Reviews



Average ratings
5.0
Guides
5.0
Quality of itinerary
5.0
Food quality & variety
4.8
Value for money
4.6
Right amount of activity
5.0
Overall satisfaction

Reviews
4.8
by PaulaG
Posted Oct 12, 2022

This was my second Italy trip with CustomWalks and it was like coming home to be able to do a second tour with Francesca as guide. Friendships and relationships cannot be understated when experiencing an adventure! The trip was well organized and the food places chosen were outstanding as well as the accomodations. I came as a single to join a group that knew each other and I never once felt "left out" and that was due to the leadership of our guides. Thank you for helping to make my "bucket list" adventure happen!

5
by Mahsa F
Posted May 30, 2022

My husband and I went on the Tuscany walking tour in April 2022. I have to say that the tour was extremely enjoyable and went far above and beyond what I had expected. The cities we visited were beautiful and all aspects of the trip were well curated. The hotels were good and the food was fantastic and so plentiful - you certainly won’t be hungry on this trip! Our guide Francesca was amazing, so organized and pleasant to be with. We couldn’t have asked for a better guide. Overall, the experience was great. I would definitely come back again for another Customwalks tour!

5
by Regina M
Posted May 11, 2022

Customwalks expertly organized and planned the trip so we could fully enjoy the hiking, scenery, food, friends, gelato, accommodations and touring. Franscesca, our guide, was knowledgeable, pleasant and fun! The chosen restaurants and and hotels were outstanding! This is my second Customwalks tour and I would love to join them on another tour in the future!

4.6
by J Abraham
Posted Jul 14, 2018

Only change I would recommend is not going to San Gimignano (I'm sure I misspelled that) in the afternoon. If it's still included, I think it should be early in the day before it gets so crowded. I gave 4 starts for activity level because it was a bit of a challenge for me, but it was as advertised so not suggesting you change it.

5
by D and B Grollman
Posted Jun 29, 2018

This is our third Custom Walk and we continue to come back for another adventure because of the excellent quality of the itinerary , knowledgeable guides with a great sense of humor and attention to detail. We can vouch for their motto,"Creating Unforgettable,Often Edible Travel Experiences!

5
by Linda
Posted Jun 26, 2018

The scenery was breathtaking and what is not to love about Italian wine and food! We had an excellent guide who was knowledgeable, entertaining and energetic. The trip was everything I had expected and we are now thinking about our next walking adventure with Custom Walks.

4.8
by J Byrd
Posted Jun 26, 2018

Brett did a wonderful job showing us the best of Tuscany! The week was exactly what we wanted and more. Lots of hiking in the hills, hearing about the history of the area, sampling lots of good wine, eating a variety of delicious food, staying in unique hotels and getting a wonderful exposure to the countryside. Being able to share this experience with friends was unforgettable!

4.8
by Robert
Posted Jun 24, 2018

A wonderful trip. We would walk through the gorgeous countryside for hours and see no one else, and suddenly be at a winery for lunch!

5
by Gabrielle, Australia
Posted Apr 27, 2015

This was my first walk with Customwalks. It was a great combination of walking the ups and downs of Tuscany, and staying in small ancient towns: Volterra – encircled by the remnants of Etruscan walls and famous for its alabaster quarries and sculptures. Colle di Val d’Elsa – a walled city on a hilltop well known for its very fine crystal makers. We visited the towered city of San Gimignano and the plain, unadorned fabulous Siena. Ilaria and Manu were fun, and immensely knowledgeable and enthusiastic. We walked through land abundant with fruit trees – figs, apples, pears. Huge chestnut trees shed their prickly balls in profusion. The Pilgrim’s Way (“Via Francigena”) took us through hunting lands and fields of sunflowers. This walk is well balanced with historical interest, exercise and sampling the many Italian wines and foods of the region. Absolutely LOVED it!

4.8
by Zeke
Posted Feb 05, 2015

This is a great trip if your interests are great food, even better wines, and luxury accommodations. What you get as a bonus is great guides that will fill your week with the history and culture behind the hill towns that are Tuscany. You may find yourself learning a bit of Botany throughout the week as well. The guides are knowledgeable and always very accommodating. This is not a strenuous hike more of a relaxing week long stroll, but most enjoyable!



If you have any questions or specific requests about any of our tours, we’re here to help. You can fill in the form below, send us an email, or call us and we’ll get back to you as soon as possible.

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Contact us by email

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Italian operations office

This was my second Italy trip with CustomWalks and it was like coming home to be able to do a second tour with Francesca as guide. Friendships and relationships cannot be understated when experiencing an adventure! The trip was well organized and the food places chosen were outstanding as well as the accomodations. I came as a single to join a group that knew each other and I never once felt "left out" and that was due to the leadership of our guides. Thank you for helping to make my "bucket list" adventure happen!
by PaulaG


My husband and I went on the Tuscany walking tour in April 2022. I have to say that the tour was extremely enjoyable and went far above and beyond what I had expected. The cities we visited were beautiful and all aspects of the trip were well curated. The hotels were good and the food was fantastic and so plentiful - you certainly won’t be hungry on this trip! Our guide Francesca was amazing, so organized and pleasant to be with. We couldn’t have asked for a better guide. Overall, the experience was great. I would definitely come back again for another Customwalks tour!
by Mahsa F


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Tuscany hike lunch at winery table
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Food bellissima bruschetta!
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Hiking with lone cypress
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San gimi towers
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Vista day 5 more grapes
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Vista sunflowers and cypress
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Tuscany hike colle di val delsa pax
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