Classic Tuscany

8 Days & 7 Nights 4.7 Read 31 reviews
  • 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 over night stays in classic medieval centres
  • 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.
Walking, classic must-see hilltop towns and a smorgasboard of organic Italian cuisine and wine combine over a week of soaking up the sights, tastes and ambience of stunning Tuscany. 2 Night stays in Volterra, San Gimignano, and Siena mean you can choose to kick back and relax, sightsee, or enjoy lovely loop walks.

Tour 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 traveler this tour would be suitable for is: 12 Years

Ideal if you have an interest in:

  • Foodie
  • Wine

Activity Level & 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 between 17-25.5km 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). 


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.


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.

  • Overnights in traditional B&Bs and guesthouses (3-star standard)
  • Breakfasts included
  • Baggage transfers between accommodation
  • Taxi transfers as per itinerary
  • 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

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.

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;

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.

Luggage 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 Volterra Loop Walk or sightseeing 11 miles / 18 km Day 3 Transfer to Riserva Naturale Montenero, walk to San Gimignano 14 miles / 23 km Day 4 San Gimignano Loop Walk 11 miles / 17 km Day 5 Walk to Colle di Val D’Elsa - Option to shorten walk 16 miles / 26 km Day 6 Transfer to Monteriggioni, walk to Siena 13 miles / 21 km Day 7 Explore Siena Day 8 Onward Travel

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