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Classic Tuscany Short Break

5 Days & 4 Nights 4.8 Read 33 reviews
  • 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!

What To Expect

A 4-night break to recharge your batteries: 3 days of exploring Tuscany on foot, walking between classic hill-top towns and villages brimming with atmosphere. Explore Volterra, San Gimignano, Colle Val D’ Elsa and Siena by night, with plenty of opportunities to indulge in Chianti wine, organic aged pecorino cheese and home-made pasta.

Trip Type:

Classic Routes | If you’re the active, outdoorsy type, who’s interested in taking on the great routes of the world or looking for a challenge, then our Classic Routes are for you. We’re talking the West Highland Way, Tour Du Mont Blanc and the Passau to Vienna Danube Cycle Path, to name but a few!


Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&B’s, inns, and guesthouses.

This trip is suitable for:

Solo Travellers

As a guide, we would suggest that the minimum age of traveller this holiday would be suitable for is: 12 Years

Ideal if you have an interest in:

  • Foodie
  • Wine
  • Short Break

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 22km each day. Should you wish to skip a walk between towns then (with prior notice) you can travel in the taxi (luggage transfer). 


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.

Accommodation Information

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.

  • 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
  • Supplement to upgrade to 4-star properties
  • Transfers from Pisa/Florence/Rome

When To Go

This tour is available to start anytime between March and October.

Peak Season Availability

As Tuscany is a very popular destination, we suggest booking as soon as possible to ensure availability for specific dates. Availability in Siena is very difficult around the times of the 'Palio' horse races held annually normally in early July and then again in mid-August.

Time of Year

The springs months offer warm sunshine, fewer crowds, and pleasant walking conditions. May is when most wildflowers are coming into bloom. The autumn months of September and October are also a favourable time of year, boasting cooler weather and a striking landscape made up of autumnal colours. July and August are good months to go but can be very hot for walking and therefore aren’t best suited for everyone. You will have to start early to miss the heat of the day and carry a lot of water (additional weight) with you. Although the towns and villages are buzzing at this time of year which is great to see.

Getting to the Start

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 the End

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.

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.

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. 


Our pre-departure information pack has detailed advice and a kit list on what to take with you to Tuscany. This includes warm and cold weather gear, hiking boots, and lots of other useful bits and bobs.

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.

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Day 1 Arrive Poggibonsi/Pontedera, transfer to Volterra Day 2 Transfer to Riserva Naturale Montenero, walk to San Gimignano 14 miles / 23 km Day 3 Walk to Colle di Val D’Elsa - Option to shorten walk 16 miles / 26 km Day 4 Transfer to Monteriggioni, walk to Siena 13 miles / 21 km Day 5 Onward Travel

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