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Self Guided Walking Holidays & Cycling Holidays

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Classic Tuscany Short Break self-guided walking holiday


  • 3 Days of walking in Tuscany; Volterra, San Gimignano, Colle Val D’Elsa, Siena.
  • Rolling landscapes of vineyards, villas, woodland and medieval hilltop towns.
  • Gourmet Tuscany— local olive oils, hand-made pasta, pecorino cheeses.
  • Cobbled streets with medieval, Romanesque & Gothic churches & palazzos.
  • Robust Chianti Colli Senesi, Sangiovese, chilled Vernaccia San Gimignano.

Spend 4 nights exploring Tuscany on foot, walking between atmospheric ancient hilltop towns of Volterra, San Gimignano, Colle di Val D’ Elsa and Siena.

Soak up the views as you wander between Etruscan olive groves, vineyards and over rolling green hills. The sunlight casts impressive shadows over the undulating landscape. Foodies are in for a real treat; sweet vin santo, flavoured grappas, chilled Vernaccia from the sandstone vineyards of San Gimignano, castagnaccio chestnut cake and fruity Siena torte; it’s a good job we’ve planned out some great walks, allowing you to spoil yourself!

Day 1: Arrive Poggibonsi/Pontedera, transfer to Volterra

Your Tuscany short break begins in the hilltop town of Volterra, its well-preserved medieval ramparts affording panoramic views to the rolling landscape and over the narrow cobbled streets inside the town’s walls. This evening, relax at an authentic trattoria, where you can take your fill of fresh pasta and pecorino, washed down with deep red sangiovese and a glass of grappa.

Arriving at either Poggibonsi or Pontedera train station (both an easy train ride from Florence or Pisa), meet your taxi driver and transfer to Volterra.  

Overnight: Volterra

Day 2: Transfer to Riserva Naturale Montenero, walk to San Gimignano

A taxi transfer will bring you to the tiny hamlet of Ulignano, close to the Riserva Natural Montenero.  Wander eastwards along rural woodland tracks to reach the nature reserve of Castelvecchio.  

Pass through the tiny medieval village of San Donato set amidst classic green hills, and glimpse your first view of San Gimignano’s magnificent towers.   

Soaring on a hilltop overlooking Valdelsa, San Gimignano once boasted 72 towers (around a dozen remain today). The town is a UNESCO World Heritage Site, boasting fine examples of Romanesque and Gothic architecture. Visit the Palazzo Comunale, the Collegiate Church and Church of Sant' Agostino to see their 14th and 15th century frescoes.

Walk: 22.5 km, ascent 325m, descent 430m

Overnight: San Gimignano

Day 3: Walk to Colle di Val D’Elsa

Today you’ll walk along the famous Via Francigena, the ancient pilgrimage route which stretches from Canterbury to Rome.  You can shorten today's walk to 21km by taking the bus the final section.

Pass by vineyards and honey-hued stone hamlets to approach Colle di Val D’ Elsa through  the ancient Porta Nova, passing fine 16th- and 17th-century noble houses to arrive at the Palazzo Campana, and the castle.

Colle di Val D’ Elsa retains a proud history of creating exquisite crystal glassware and you can browse the artisan workshops and pick up a memento to take home.

Walk: 21-25.5 km, ascent 320m, descent 500m

Overnight: Colle di Val D’ Elsa

Day 4: Transfer to Monteriggioni, walk to Siena

Monteriggioni is a short transfer away, set amidst the gentle Sienese hills and a rare example of medieval military architecture, with its 14 square towers.

Leaving Monteriggigoni on foot, follow in the pilgrims footsteps along the Via Francigena to Siena.  Siena’s layout is still as it was in its heyday of the 14th century, when Sienese art and economy rivalled that of Florence. With so much to see, this is the ideal spot to spend your final night in Tuscany.

Walk: 21 km, ascent 345m, descent 265m

Overnight: Siena

Day 5: Onward travel

Bid a fond ‘arrivederci’ to Tuscany after breakfast.  From Siena you can catch the train to Florence or on to Pisa, or perhaps continue your journey further within Italy; Tuscany combines perfectly with our coastal walks of the Cinque Terre or Amalfi Coast.


4 nights accommodation is included in your trip.  We’ve carefully selected our ‘comfort’ properties; charming lodgings of character, small family-run agriturismo, and charming village B&B’s that will make your stay in Tuscany extra memorable.

The accommodation we normally use is detailed below and on our website, however are subject to availability and therefore alternatives of an equal standard may be offered. You can add on extra nights in any of the overnight locations on this tour.

Accommodation Upgrade

Alternatively, you can pay a supplement for
‘superior’ properties which include former convents, monasteries and
stylish villas.

Single Rooms & Solo Walkers

This trip is available to solo walkers and a supplement is payable as some of the costs (such as transfers) are not shared. Single rooms are on request and a supplement is payable.


Tuscany’s tempting food and wine is a highlight of this trip.  There are countless fantastic restaurants throughout the region, and on the walks you’ll come across some real gems in the form of fattoria and agriturismo (farms making olive oil, cheese, pasta, saffron and wine), just begging for you to stop and enjoy their local produce.

In order to keep things flexible, dinners and lunches are not included, as you will be spoilt for choice!

The price of your tour includes breakfast each morning.  Lunch and dinner are not included so you are free to choose from the available options. Most of your accommodations will more than happy to provide a packed lunch on request and this can be booked on arrival.




Albergo Etruria - Volterra

Albergo Etruria - Volterra

Albergo Etruria is found in the historic center of Volterra, in the main shopping street, just 100m from the famous Piazza dei Priori. The property dates from 1700 and each of the 18 hotel rooms have a private bathroom with shower, access to free Wi-Fi, TV, telephone. There is a lovely garden for guests to relax. There is no lift, but luggage service is included.







Rifugio dei Sogni - Volterra

Rifugio dei Sogni - Volterra

A lovely farmhouse with apartments, just 2km from Volterra. The property produces wine (2 whites and 5 reds) and olive oil. Tours of the farm (including a guided tasting of wine, grappa, olive oil, local cheese and toscano ham) are approx.EU20 per person. Dinners are on request.







Le Undici Lune - San Gimignano

Le Undici Lune - San Gimignano

This charming 4-bedroom B&B is located with spectacular views of the towers of San Gimignano. Stay in a 14th century property. 39 steps lead to the ‘Eleven Moons’ B&B, with its personable atmosphere and family-run friendl service. Free WiFi.







B&B Arnolfo - Colle di Val D'Elsa

B&B Arnolfo - Colle di Val D'Elsa

The Arnolfo B&B, next to the ponte di Campana, is a comfortable B&B, divided into three apartments wth a total of 10 rooms (each with own bathroom with shower, Wi-Fi and satellite Tv. There is a guest lounge/reading room with internet access and a small garden.







La Chicca B&B - Siena

La Chicca B&B - Siena

La Chicca B&B is run by the Garavini family. The accommodation is situated in an old villa in the San Prospero area, just outside of the historic Siena’s walls. It’s just a 5 mins walk from the Piazza Campo. The B&B has 6 double rooms (3 are en suite, 2 have an external shared bathroom) which are spacious, bright and comfortable. There is a cellar and a garden with private terrace. Free WiFi.







Hotel San Lino - Volterra

Hotel San Lino - Volterra

Hotel San Lino was originally built as a convent in 1480 and remained as such until 1982 when it became an hotel.The rooms facing the Via San Lino street offer guests a view of one of the most beautiful medieval streets, whilst the rooms located on the internal side of the hotel offer a view of the small garden, swimming pool and tiny church of San Lino. The accommodation is spread over three floors, and occupies the nuns’ original sleeping quarters. It is the only hotel situated within the city walls that offers a viewing terrace and pool with sunbathing terrace. Guests can dine in the I Papi restaurant. Rooms have Wi-Fi, minibar, telephone, safe, satellite TV, air conditioning, private bathroom with shower and hairdryer.







La Collegiata - San Gimignano

La Collegiata - San Gimignano

La Collegiata is located 2km outside of the city walls, in a peaceful location. The property has a fascinating history; In 1587 the people of the village decided to build a monastery in honour of the Cappuccini monks who helped the population during the difficult times. The monastery was onsacrated in 1599. It was occupied then abandoned in Napoleon’s era, and eventually became a hotel in 1988. All 20 rooms are beautifully furnished with echoes of the past. There is a lovely pool and a fantastic restaurant L’Eco Divino (closed Mondays). There is also a small wine bar overlooking the cloister.







Palazzo Pacini - Colle di Val D'Elsa

Palazzo Pacini - Colle di Val D'Elsa

Situated in the old part of Colle Val d'Elsa, the Hotel Palazzo Pacini Residence offers a welcoming atmosphere of elegant grace and charm, in the peace and quiet of Colle's “Borgo” neighbourhood. Guests can enjoy a complimentary 1-hour wine tasting at Enoteca Il Salotto in Colle Val D’Elsa. Rooms have Wi-Fi access, air-conditioning, flat screen plasma TV, safe, minibar and private bathroom.







Il Chiostro del Carmine - Siena

Il Chiostro del Carmine - Siena

The hotel occupies an ancient Convent built at the end of the 13th century in the old town area of Siena known as the Rione of Castelsenio. The rooms are comfortable and bright, with free WiFi, satellite TV, air conditioning, minibar and safe. Guests can relax in the tranquil courtyard; a green refuge in the heart of the city. Please note that there is no lift at this property. A porterage service is available on request.





You can start this walking tour anytime between May and October. Tuscany is very popular so it’s best to book as far in advance as you are able to.  Please bear in mind that July and August can be hot for walking. Availability in Siena is very difficult around the times of the 'Palio'
horse races held each year on the 2nd of July and the 16th of August.

Single Rooms & Solo Walkers

This trip is available to solo walkers, although a solo walker supplement is payable as some costs (such as luggage and taxi transfers) are not shared. If you require single rooms within your party then we can request this, and a single supplement is then payable. Please remember that with smaller properties the number of dedicated single rooms will be limited.

Grade & Terrain

This trip is graded ‘moderate’ overall, as the  terrain is hilly. Most of the route follows gravel and farm tracks and trails, and you will be following minor roads only occasionally. You’ll be walking up to 25.5km each day. Should you wish to skip a walk between towns then (with prior notice) you can travel in the taxi (luggage transfer). 

Navigation, Route Notes & Maps

The route is not waymarked (with the exception of some sections where you will be walking on the pilgrimage route the Via Francigena), and we supply detailed 1:50 000 Kompass maps and route notes so you will have no problem finding your way.

Baggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight stay. We ask you to limit your luggage to one bag of up to 20kg per person.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.

General Information

The distances and ascent/descents are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants), sun hat, sunscreen. Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack. 

Getting to Pontedera/Poggibonsi

By Air: We recommend flying to Florence or Pisa and then you can catch the train from the city centre to Pontedera (train from Florence approx. 45mins, Pisa 15mins) or Poggibonsi (train from Florence or Pisa approx. 1h15).  

A taxi transfer from either Poggibonsi or Pontedera train station to Volterra is  included in your trip arrangements. Train timetables are available at Trenitalia; www.trenitalia.com

Getting from Siena

From Siena you can take the train back to Pisa (1h45), Florence (1h30) or Rome (3hrs). Again, please see Trenitalia’s website for timetable planning.


  • 4 Nights in traditional B&Bs and guesthouses (3-star standard).
  • 4 Breakfasts.
  • Baggage transfers between accommodation.
  • Taxi transfers as per itinerary (days 1, 2, 4).
  • Route notes, maps and detailed information pack.
  • 24-7 Emergency telephone support.


  • Travel insurance (required).
  • Travel to Pontedera/Poggibonsi and from Siena.
  • Lunches, dinners, drinks and snacks.
  • Personal equipment.


  • Additional nights before, during or after the walk.
  • Solo walker supplement.
  • Single room supplement if required.
  • Supplement to upgrade to 4-star (superior) properties.
  • Transfers from Pisa/Florence/Rome.

We are often asked the following questions and we hope that you will find the answers useful.

How fit do I need to be?

This trip is graded ‘moderate’ overall, as the  terrain is hilly. Most of the route follows gravel and farm tracks and trails, and you will be following minor roads from time to time. You’ll be walking up to 25.5km each day. Should you wish to skip a walk between towns then (with prior notice) you can travel in the taxi (luggage transfer).  You should have a good level of fitness, to make the most of this trip.

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised as the region is extremely popular. The accommodations mentioned on our website are those that we normally use and are subject to availability at the time of booking, however we will always try and accommodate your plans.

What personal equipment do I need?

You will need good walking shoes/boots (ideally waterproof), comfortable walking clothes, and dependent on when you are travelling; waterproof jacket and trousers, a daypack and hats/gloves etc. Our info packs have a list of all equipement to bring on your walk.

When is the best time of year?

If you prefer to walk in cooler months then May and September/October will be perfect for you.  The autumnal colours are spectacular in Tuscany.  The summer months (June, July, August) can be very hot. 

What happens if I don't want to walk?

You can (with prior notice) join the taxi which is transferring your luggage, and therefore avoid walking between hotels if you wish.  Alternatively, you can use public transport or local taxis to move you to the next overnight stop.  


Tuscany in October


Mostly self -guiding was straightforward enough using the notes, maps and occasionally compass. We didn't use the app. In some places distances were incorrect - 10 metres in the notes when actually 50 metres on the ground but we could usually find the route though we were puzzled about how such a discrepancy could arise.

An Spailpín Fánach


Excellent trip


The hike through Tuscany was the highlight of our recent holiday. Maps/instructions were perfect, time estimates right on. Accommodations were lovely, well-chosen. We were glad we'd downloaded the app, as our luggage, including trip details, was lost and took a few days to catch up. Great to have it! We were fortunate with weather, and this style of travel -- on our own but with all details handled by someone -- suited us well. Thanks for an amazing experience!


Minnesota USA

Well organised trip in stunning location


The trip was very well organised from start to finish. The transfers all went smoothly and the accommodation was generally excellent. The towns on route are amazing with San Gimignano a particular highlight. The recommendation to eat at the Fattoria on the loop walk was a superb suggestion. We did the trip in 1st week of September so the only advice I would offer fellow travellers is to bring warm layers for the evenings!



Just - WOW


Macs - what can I say. Thank you so much for this adventure. Even though I walked during the heat wave and my mum had to pull out, this was one incredible experience. The trip notes were excellent and the accommodations and transfers were incredible for my mum who missed out on walking because of the heat. You sprang into action when we needed you and we couldnt be more grateful. We will be recommending to all our friends and we cant thank you enough!

Brooke Mills

Sydney, Australia

A wonderful well organised trip


Macs gave great service and good advice - yes it was hot and I would agree with Macs not ideally done in height of summer but we managed. All information provided for the walk was accurate, though I don't rate compass maps, and the timings were spot on - even in 30+ deg. heat. The accommodation was as billed and overall of excellent quality, and all the transfer arrangements worked seamlessly. An excellent way to see a wonderful part of the world in a slightly different way. We were even lucky enough to see a family of wild boar.



Classic Tuscany


WE had a blissful few days walking between Volterra and Siena, partly on the Via Francigena. The company organising transport Bacci Travel were excellent - very friendly and nice. The accommodation was good, especially at La Collegiata in San Gimignano and Il Chiostro in Siena. The walking route was very well-chosen and described in the route notes. The route notes could do a better job of describing dining options. We arrived the day of the Palio in Siena and this was not mentioned in the route notes.

Peter Hall



I would definitely do a Macs Adventure again!


We would definitely do another Mac's Travel trip. Overall, we were very happy. The directions were excellent. We didn't take a single wrong turn. The app is excellent as well. My husband loved having the app and I loved the written directions. The accommodations were very suitable. Would definitely recommend this trip. I just would encourage the staff to work harder to make sure that the clients get their documents in the mail. Unfortunately, we never received the hard copy of the documents before we left for our trip. Considering the cost of our trip, I would highly suggest that the person working with us ask when exactly we are planning on departing our home country and spend the money to express mail the documents. Going on this trip with three children without documents started the trip off with unnecessary anxiety. A person on the phone emailed me some documents, but by that time we had already departed and could not easily print the docs. Since several of the reviews say the same exact thing, there seems to be a problem in how they are doing this. I was told that you would have the docs ready at our first point of departure and when we arrived, they were not there. I called Macs and someone immediately helped me and made sure that we had the app. I appreciate how helpful that person was. There were two packets at the front desk of the hotel that had arrived after earlier guests had left and we took those notes which were almost identical except for the last night of the hotel. This worked out well until the last night when I went to the hotel that was on the documents because I was delirious from hiking almost 25 kilometers. Unfortunately, it was the wrong hotel and not the one I was supposed to be staying in. Luckily the man at the front desk helped me order a cab to the B & B that we were staying in. Overall, we enjoyed the trip and would love to do another one!

San Francisco traveler

San Francisco


Great self guided walking tour


My friend and I had an amazing time walking through Tuscany. It was a great opportunity to see the classic Tuscan countryside and stay in some lovely towns in great accommodation. The taxi drivers were great. We often opted to walk a slightly shorter distance and the drivers would do their upmost to help us out. Have recommended macs adventures already to friends and family.






This trip was part of a 2 week vacation in Italy in between a 3 day stay in Florence and before a 3 day stay in Cinque Terre. The self guided walks and Macs moving our bags from village to village is what appealed to us. The scenery was spectacular!!!. The walks and villages were great. Although a few of of the directions were off and others a little ambiguous, most of it was spot on. The accommodations were great. Very friendly inn keepers the whole way. Several of the inns were away from the bulk of the tourists. The food and wine were of course awesome. Macs organized this trip very well and they were extremely accommodating to minor changes we needed to make to the itinerary because of weather. Well done.

Misty and Bob

North Carolina


Classic Tuscany


The walking holiday was the perfect way of getting to know Italy and her people as well as taxing the body to do more than I thought possible.


Dublin, Ireland


Classic Tuscany

4.9 10


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