Self Guided Walking Holidays & Cycling Holidays

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Self-guided walking holiday in Tuscany


  • Walking in Tuscany; Volterra, San Gimignano, Colle Val D’Elsa, Siena.
  • Quintessential hilltop towns and villages amidst vineyards and farmland.
  • Lazy lunches of fresh organic produce —olive oil, pasta, cheeses & wines.
  • Relaxing 2 night stays in classic medieval centres, with optional loop walks.
  • Wine! Red Chianti Colli Senesi, Sangiovese, chilled Vernaccia San Gimignano.

Treat yourself to a week under the Tuscan sun; slow down to take in the classic sights of Volterra, San Gimignano, Colle Val D’Elsa Monteriggioni and Siena on foot—the best way to relax and immerse yourself in Tuscany.

Follow trails between hilltop towns, set against an undulating patchwork of vineyards and villas. Farmhouse lunches are filled with local organic gourmet goodies— matured pecorino, soft ricotta, homemade pasta, saffron treats, sweet vin santo and castagnaccio chestnut cake. This week-long trip includes 2 nights each in Volterra, San Gimignano and Siena, combining rewarding walks with time to lose yourself in the medieval, Renaissance and Gothic architecture.

Day 1: Arrive Poggibonsi/Pontedera, transfer to Volterra

Slow down and savour a week of walking through quintessential Tuscany—starting in the classic Etruscan city of Volterra, perched 1770ft above sea level, with its 1120 Duomo (cathedral), and fascinating ruins. 

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: Volterra Loop Walk or sightseeing

Start with a transfer to the trailhead, then set off on a rewarding walk which explores the gently undulating landscapes north west of Volterra, dotted with picturesque villas and poker-straight cyprus trees. Follow strada bianche (gravelled roads) and footpaths across rolling farmland.

Walk: 18 km, ascent 530m, descent 250m

Overnight: Volterra

Day 3: Transfer to Riserva Naturale Montenero, walk to San Gimignano

After breakfast your driver will transfer 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 4: San Gimignano Loop Walk

You can choose to explore San Gimignano’s medieval walls, piazzas and climb its towers, or venture into the patchwork landscape of vineyards and woodland for a rewarding 16km loop walk.

A lovely place to stop for a ‘light lunch’ is the rural farmhouse at Fattoria Poggio Alloro. Relax and soak up the views of San Gimignano from the terrace as you feast on bruschetta, pasta, fresh green salad, pecorino cheese, prosciutto, salami, red and white wine, rounding off with a  sweet taste of vin santo and cantuccini biscuits.  Take your time winding the 5km back to San Gimignano.

Walk: 17 km, ascent/descent 530m

Overnight: San Gimignano

Day 5: Walk to Colle di Val D’Elsa

Ahead lies a long but enjoyable day of walking along the famous Via Francigena, the ancient pilgrimage route which stretches from Canterbury to Rome. You can shorten the walk to 21km by taking a bus for the final 4.5km.

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 6: 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 2 nights in Tuscany.

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

Overnight: Siena

Day 7: Explore Siena

You’re free to explore all that Siena has to offer today.  The Campo, or main square, is at the very core of the city.  Shaped like a scallop-shell, the Campo is the setting for the famous Palio horse race. 

Built on a Y-shaped ridge, immerse yourself in Siena’s steep and narrow ancient streets, scattered with architectural gems; amongst them the Gothic Duomo and Palazzo Pubblico, as well as numerous churches.

Overnight: Siena

Day 8: 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.


7 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 from time to time. You’ll be walking up to 25.5km each day, and on 2 days the loop walks are optional. 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;

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.


  • 7 Nights in traditional B&Bs and guesthouses (3-star standard).
  • 7 Breakfasts.
  • Baggage transfers between accommodation (days 3, 5, 6).
  • Taxi transfers as per itinerary (days 1, 2, 3, 6).
  • 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 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 only occasionally. You’ll be walking up to 25.5km each day, and on 2 days the loop walks are optional. 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.  There are three walks where you'll be walking between accommodations, but on the other days the loop walks are optional so you can choose to explore on foot or simply relax.


Great experience in Tuscany


We did this with another couple and had a great time. All transfers showed up exactly on time, hotels were great and were expecting us. The hiking directions were very clear. Definitely will recommend Mac's adventures to others and use them again in the future. The only comment we have is that Hotel Duomo in Sienna is looking a bit tired, carpets not very clean and we had noisy rooms as there seemed to be a bar below. It did have beautiful views though.




Great Trip!


This was a great holiday, very well organised. The booking process was faultless, all pick ups were seamless and the accommodation was superb. My only comment would be that for some of the walks the instructions were misleading. Otherwise a fabulous trip!

HK Dteam



Great trip. Everything went as planned.


We were picked up on time. The accommodations were worthy of a once in a lifetime experience. And the mapping app worked perfectly.




Walking under the Tuscan Sun


This trip was very well organised from the support we received early on from Shaun, to the information packs and apps. Everything was run really smoothly which meant we just had to focus on the walking. The walk was a challenge, its long and hot (in June) but beautiful and the accommodation was very comfortable in beautiful locations. Take some good boots!




Very good trip


Comfortable accommodation, good breakfasts, excellent directions. We enjoyed the adventure and the beautiful landscape of Tuscany.




Fabulous 3 days walking in the Tuscany countryside


We all really enjoyed our walking holiday in Tuscany. Craig of MacsAdventure organised everything brilliantly and it all worked like clockwork. He also reassured us 50 somethings that we would be able to do the walking (between 20 and 25km a day) and that we would also be able to train it back to Pisa airport from Siena. The Tuscany countryside was stunning and it was wonderful arriving at the beautiful hilltop towns at the end of each walk. The accommodation you booked us was great - the hotel in Volterra and B&B in Siena standing out. Mainly because the owners were so charming and helpful.




Fantastic Tuscany


Really enjoyable trip and some great accommodation locations. Well done Macs Adventures for sourcing the accommodation, it really is the icing on the cake after a long day of walking. The pool at Rifugio Dei Sogni was beautiful and very refreshingly cold...brrrrr. Just be aware that some of the walking routes finish up on main roads into the towns so extra care is needed.

Sore Feet Dave



Lovely walking in beautiful countryside


This was very well organised trip, transfers were excellent, accommodation of a good standard and maps and routes good. The accommodation was of a good standard and the routes well chosen, although I would recommend using the app in conjunction with the map. It was excellent, even telling us we walking on the wrong side of the road as we walked into Sienna ! best of all though the scenery was stunning. I would recommend late September as the weather was perfect for walking.




I would definitely book another Mac adventure holiday


Brilliant holiday Walking guides easy to follow and adaquately descriptive Walking distances accurate Mac adventure app very user friendly Taxi service at beginning of walks very punctual Very good accommodation A thoroughly enjoyable holiday

Tuscany walkers



Nice taste of Tuscany


First time ,with MacsAdventure. Well organized.

Foot flat

Sandefjord Norway


Classic Tuscany

4.7 26


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