Self Guided Walking Holidays & Cycling Holidays


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Classic Tuscany Short Break self-guided walking holiday
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Highlights

  • 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.

Accommodation

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.


Meals

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.


 

 

 

Availability

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.

Included

  • 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.

Excluded

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

Extras

  • 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.  

 

Walking under the Tuscan Sun

5

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!

Serena

UK

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Very good trip

5

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

Sher

Umbria

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Fabulous 3 days walking in the Tuscany countryside

5

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.

Mimi

Elstead

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Fantastic Tuscany

4

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

London

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Lovely walking in beautiful countryside

5

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.

Kelly

Bristol

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I would definitely book another Mac adventure holiday

5

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

Chepstow

true

Nice taste of Tuscany

5

First time ,with MacsAdventure. Well organized.

Foot flat

Sandefjord Norway

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Enjoyed our walking tour but some problems with directions

4

Great accommodations and luggage transfers. Difficulties with some of the directions provided by macs. App was helpful but need to keep in mind that travellers from US and Canada have to pay for data in Europe so will only use the app in emergencies. Several errors in printed materials. Will send by email details of errors.

Rita the walker

Canada

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Fabulous

5

Excellent holiday - beautiful countryside. The standard of accommodation was excellent - could not fault any of it - just what you needed after a long hot day. The organisation was excellent - drivers were well informed, helpful and punctual. This was our first holiday with Macs Adventures and will not be the last - already planning the next one. Thank you.

Liz & Kev

Northumberland

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Beautiful Tuscany

5

This amazing walk highlights the beautiful Tuscany countryside. Spring was a great time to do the walk, to enjoy the spring flowers and for picking cherries off the trees. This walk was quite hilly and the weather in early June was hot, so I would recommend this walk only to very keen hikers. I found the written instructions confusing at times and realised later that I should have used the app with the map/GPS in preference. Overall this was a wonderful experience.

Maz

Australia

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Classic Tuscany

4.7 23

100.0

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