Walking tours


Tuscany Walk – Chianti, Siena & Volterra

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  • 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 2019: May 5, 12 & 19, June 2, Sept 8 & 22, Oct 6
  • Price 2019: Euro €3,050 per person in double occupancy. Single supplement Euro €350. One guide accompanies departures of 2 - 8 people. Two guides accompany departures of 9 or more people.
  • Departures 2020: May 3, 10, 17 & 31, Sept 6 & 20, Oct 4
  • Price 2020: Euro €3,100 per person in double occupancy. Single supplement Euro €350. One guide accompanies departures of 2 - 8 people. Two guides accompany departures of 9 or more people.

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 walking through some of the most beautiful countryside in the world. [Read an article about our Tuscany Walk that appeared in New Zealand’s “Otago Daily Times” written by deputy editor Simon Cunliffe. Click here.]

Tuscany Walk – Chianti, Siena & Volterra itinerary

Day 1 – Sunday (Saturday May 5 departure)

Meet your guides this morning at 9 a.m. at the Hotel Orto de’ Medici and head out on an urban trek up and out of Renaissance Florence. Cross over the Ponte Vecchio and go up a hidden lane to the basilica of San Miniato, one of Italy’s most beautiful medieval churches. From there you continue to the Pian dei Giulari, a plateau overlooking Florence and the rolling hills of Chianti to the south. You’ll pass Renaissance villas as well as Galileo’s observatory and the Forte Belvedere, designed by Michelangelo to defend the city from the advancing Spanish. From here you’ll have a van transfer to the Chianti countryside for a light lunch in the walled hamlet of Vertine. Afterwards, we walk among vineyards, olive groves, and stone farmhouses to the Castello di Spaltenna, a 12th century fortified convent that has been transformed into a beautiful five-star hotel. Relax by the pool before an aperitivo and dinner in the village. The Walk: 2 hours in the morning (9.5 kms) and 1.45 hours in the afternoon (7 kms). Overnight Gaiole in Chianti. Breakfast, lunch and dinner included.

Day 2 – Monday

This morning’s walk takes us out into the vineyards around the hotel. A short climb takes us to Meleto Castle for a visit of this extraordinary monument that has evolved over the centuries. It started off as an 11th century tower, then became a 14th century walled castle, then a Renaissance summer villa, and finally a Baroque showpiece in the 1700s. We continue on to a wine tasting at the Rocca di Castagnoli, which produces award winning Chianti Classicos and “Super Tuscans.” We’ll have lunch at the nearby trattoria. In the afternoon we loop down through the hamlet of Bricciano (where Customwalks has its Italian headquarters!) and back to Gaiole and Spaltenna. The walk: 2 hrs in the morning (7.5 kms); and 2 hrs in the afternoon (7 kms). Overnight Gaiole in Chianti. Hotel, breakfast, lunch and dinner included.

Day 3 – Tuesday

Take a break from hiking today and transfer by van to beautiful Siena, one of Italy’s most enchanting cities. Siena succumbed to Florence in 1585 with the result that it was frozen in time, making it today one of Europe’s best preserved Gothic cities. “Il Campo” is considered by many to be Italy’s most beautiful square. We have a walking tour with a local guide who will explain the mayhem and passion of the famous bareback “Palio” horse race that is run around the piazza twice a year. You will have free time to explore Siena’s shops and historic buildings before regrouping at 16:00 for a van transfer to Colle di Val d’Elsa, an authentic Tuscan hill town whose historic center still thrums with the rhythms of everyday life. Colle is also home to Italy’s finest crystal makers, whose beautiful creations can be found in small shops throughout the town. Our hotel is the Palazzo San Lorenzo, another historic building that has been transformed into a designer four-star hotel with spa and wellness center. We dine in a local trattoria a short walk from the hotel (some departures stay in the lovely Arnolfo B&B). Overnight Colle di Val d’Elsa. Hotel, breakfast and dinner included. Lunch not included.

Day 4 – Wednesday

Depart on foot from the hotel to exit Colle’s ancient city wallsd directly into the countryside. Our path follows the “Via Francigena,” the medieval pilgrimage route that linked Rome to the rest of Northern Europe from as far back as 800 AD. We stop for lunch at a country residence that was formerly a 13th century monastery. We’ll have a sweeping view from the terrace to the rolling Tuscan hills and the distant towers of San Gimignano. Return to Colle on foot and then have free time to peruse the crystal shops or visit the fascinating museum of crystal. Tonight is a “free night,” so you can choose from a variety of authentic local trattorias and restaurants that your guides are happy to suggest. The Walk: 3.5 hours (14 km). Overnight Colle di Val d’Elsa. Hotel, breakfast and lunch included. Dinner not included.  

Day 5 – Thursday

We bid farewell to Colle and have a short van transfer to start our walk. Our route affords us wonderful views onto the storybook “city of the towers,” San Gimignano. We pass the imposing Villa Monte to finish at the Pieve a Cellole, a beautiful church consecrated in 1238. We’ll have a special lunch today at Cesani, a small family-run winery which produces excellent Chianti and Vernaccia. We have a brief visit of the winery with Letizia, the owner and wine-maker, followed by a home-cooked lunch in which each course is paired with one of their wines. From here we transfer to San Gimignano where we will have a few hours to explore this fascinating medieval village before transferring to Volterra, a walled town that has been inhabited for over 2,600 years. We dine tonight at one of the town’s traditional restaurants. The Walk: 3 hours (15 kms). We stay at the Volterra In Hotel. Overnight Volterra. Hotel, breakfast, lunch and dinner included.

Day 6 – Friday

A 30-minute van shuttle takes us to the start of our walk to the hamlet of Ulignano and a picnic lunch. The countryside here is very different from the rolling, wooded hills of Chianti. Here, the hills are much more open, and the views are vast. We walk beside expansive wheat fields, past solitary cypress trees and stone farmhouses, before eventually looping back towards Volterra, whose towers and steeples stand out across the valley. This afternoon we have a fascinating guided walking tour of Volterra, whose history spans the Etruscan, Roman, Medieval and Renaissance periods. We visit the incredible Etruscan Museum, where 2,500-year-old funerary urns, ceramics, and filigree gold jewelry bear witness to the extraordinary sophistication of the Etruscan civilization. Dinner tonight is a real treat, and an appropriate finale to a wonderful week of hiking, culture, and wonderful cuisine and wine. The Walk: 3.5 hours (13 kms). Overnight Volterra. Hotel, breakfast, lunch 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.

The Walks

The walks 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).

Useful Links

The City of Florence : everything you need to know about the city
The Accademia:  home of Michelangelo’s David and other world-famous works and The Uffizi Gallery: one of the greatest collections in the world. We recommend you make reservations ahead of time. The official site for both the Uffizi and Accademia is http://www.b-ticket.com/b-ticket/uffizi/default.aspx  and http://www.Uffizi.org where in addition to ticket reservations useful information about the museum the artworks, the events,
and what visitors need to know before visiting the gallery.
The Duomo: one of the wonders of the Renaissance, Florence’s cathedral.
The City of Volterra tourist authority: official site of the city and its activities.
Alabaster in Volterra: information on this ancient craft and the city’s craftsmen.
Siena Tourist Information: details on the city’s history and events.
Chianti Classico wine consortium: a site devoted to this world-renown wine and its group of producers
UNESCO World Heritage sites in Italy: come see the marvels that await you in Italy!

Activity Level 3 = 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 walking 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 walking and who have good balance and who are coordinated. 
Moderate Tours: Tuscany ChiantiDordogne WalkSicily WalkLake Como Walk, and Corsica

Trip Cost Includes: Six nights’ accommodations in four and five star hotels (2 nights Gaiole in Chianti at Castello di Spaltenna, 2 nights Colle di Val d’Elsa at Palazzo San Lorenzo, 2 nights Volterra at Volterra In); 6 breakfasts and 5 dinners, 5 lunches; at least one Customwalks guide (a second guide is added on groups of 9 or more) to accompany the tour and lead you on the walks; all visits and entrances as noted in the itinerary; and all transfers and luggage transport from pick-up in Florence on Day 1 until drop off at Florence train station at the end of the tour. 

Booking: e-mail us at info@customwalks.com to receive a booking contract (or use the 'Contact Us' link at the top of this page), or click on the 'Book Now' button to the right.

Insurance: We highly recommend the purchase of Trip Insurance. We recommend “Travel Guard” to our North American clients, just click on the logo below.  Australian, New Zealander, and British travelers, please consult your insurance brokers.

travel Guard insurance

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.

4.90 out of 5
Ratings based on 8 Verified Reviews

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

by J Abraham from USA Atlanta
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.

by D and B Grollman from Atlanta Ga USA
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!

by Linda from Canada
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.

by J Byrd from Atlanta, GA
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!

by Robert from USA
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!

by Gabrielle, Australia from 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!

by Zeke from USA
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!

by Marty from USA
Posted Feb 01, 2015

Three friends and I did the Chianti walk in May 2014. The entire trip was outstanding. Our guide Sara made the trip for all of us. She was personable, knowledgeable, and fun! The people, scenery, food, & wine were wonderful. We walked 6-9 miles each day. I would like to travel with Custom Walks again in the future.

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.
by J Abraham from USA Atlanta

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