Classic Tuscany Short Break

This is a 4-night active hiking adventure in Tuscany: enjoy 3 days of exploring Tuscany on foot, hiking 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.

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&Bs, inns, and guesthouses.

Solo Travellers, Families with Teens

The minimum age for this tour is: 16 Years

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 occasionally. You’ll be hiking up to 22km/13.7mi each day. Should you wish to skip a hike between towns then (with prior notice) you can travel in the taxi (luggage transfer). 

We’ve carefully selected our ‘comfort’ properties; charming lodgings of character, small family-run agriturismo, and charming village B&Bs 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 Hikers

This trip is available to solo hikers 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 are a highlight of this trip. There are countless fantastic restaurants throughout the region, and on the hikes 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 spoiled 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 be more than happy to provide a packed lunch on request and this can be booked on arrival.

The route is not waymarked (except for some sections where you will be hiking on the pilgrimage route the Via Francigena), but navigation is straightforward using the Macs Adventure App which has maps, GPS tracks and daily route information. Simply download the GPS tracks for offline use and follow the route on your smartphone with the assurance that navigation on this tour will be made simple. You will find more information on downloading the app in your Macs Adventure Account. Rest assured that by downloading the route maps in our app, this will continue to work even in areas without any mobile or internet reception.  

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 challenging around the times of the 'Palio' horse races, which are held annually in early July and then again in mid-August over the course of 4 days each month.

Time of Year

The Spring months offer warm sunshine, fewer crowds, and pleasant hiking conditions. May is when most wildflowers are coming into bloom. The autumn months of September and October are also a favorable time of year, boasting cooler weather and a striking landscape made up of fall colors. 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. The towns and villages are very vibrant at any time of year, which makes for a great atmosphere, yet as soon as you get on the hikes its relatively quiet and peaceful.

This trip starts in Volterra and includes a transfer from either Pontedera or Poggibonsi, where an included taxi will transfer you directly to your hotel in Volterra.

To reach Pontedera or Pogginbonsi, we recommend flying into Pisa Airport (PSA) or Florence (FLR), however, flights in and out of this airport are limited.

If arriving in Florence: There’s a tram that departs approx. every 10min that will take you to Florence’s main railway station – the Santa Maria Novella (takes 20min). From there it's a 45min train ride to Pontedera or 1H15 to Poggibonsi.

If arriving in Pisa: From the airport take the PisaMover that departs approx. every 10min to the Pisa Centrale Train Station (takes 5 minutes). After exiting Arrivals, follow the signs for the PisaMover, turning left and walking along the passageway to the little Pisamover station at the end of this passageway. You can either take the stairs up or go up to the platform with the elevator. Once upstairs you can buy a ticket from the machine. From Pisa Centrale Train Station, trains to Pontedera take 15mins or 1H15 to Poggibonsi.

Please check the Trenitalia website for timetable planning. Please note that not all buses/trains run on a Sunday, or they may have a reduced timetable.

If you’d prefer to avoid public transport from the airport, a private transfer can be requested. Please let us know at the time of booking if you would like to add this option (additional costs apply). Once your trip is confirmed please share your flight information with us, including your arrival time, as soon as you have booked your flights, so that we have those details well in advance and we can arrange the transfer for you ahead of time. 

It's easy to travel from Siena by train to the major airports of Florence, Pisa, and Rome.

The Siena Train Station and Bus Station are located in the valley below the city center. (about a 2km/1.25mi walk from the majority of accommodations we use). To make your way to the station you have a few options (each payable locally): 1) take the escalators 2) take a bus or 3) take a taxi.

Approx. total journey times from Siena are:

To Florence 2H15 – 3H15

• The train to Florence Santa Maria Novella station is usually a direct train that goes via Empoli and takes around 1H30. Some trains are direct whereas others go via Empoli.

To Rome 2H15 – 3H20

• To Roma Termini Train Station it’s normally necessary to change trains in Florence or Chiusi-Chianciano Terme and takes around 3H30.

To Pisa 2H00 – 3H15

• To Pisa’s Train Station there is usually a train that departs approx. every 30min that goes via Empoli and takes around 1H45.

Once again it will be necessary to travel from the central train stations in these cities back to the airports (see ‘Getting to the Start’ for further information about this).

Alternatively, we can arrange a taxi from Siena to your departure city or airport. Please let us know in advance if you wish to include this option for an additional fee.

Please check the Trenitalia website for timetable planning. There are also local buses that you can take for your onward travel and you can find the information here. Please note that not all buses/trains run on a Sunday, or they may have a reduced timetable.

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/44lbs per person.