This tour is geared towards those who like 'the finer things in life’: traditional gourmet cuisine, some of the best red wine in the world, and outstanding hotels. Of course, you should also love hiking, and on this trip, you take ‘easy to moderate’ graded hikes following trails through classic Chianti landscapes where time has stood still. There are numerous ascents/descents on the hikes, due to the nature of the hilly Tuscan scenery. If time allows, we suggest adding an additional day at the end of the trip in historic Siena to soak up the atmosphere and rejuvenate before continuing with onward travel.

In Style | After a day of exciting adventures and soaking up unbeatable scenery, retreat to stylish accommodations and unwind with fine food and wine. This trip type is for those who like sophisticated places to stay and are looking for active routes but still want the holiday to feel special.

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: 12 Years

This trip is graded ‘easy to moderate’ overall. The terrain is hilly with regular ascents and descents, and summer temperatures can be high. You should therefore be in good physical fitness to fully enjoy the hiking on this tour. Most of the route follows gravel and farm tracks and trails, and minor roads from time to time. It’s best to train ahead of time and do some practice hikes including stairs and ascents and descents like those you will experience on the trip while carrying your day bag. The hikes are an average of 15-16 km (9.3-10mi) each day and a couple of them are optional and could be skipped if an additional rest day is required. However, should you also wish to skip a hike between towns then you will be responsible for taking a taxi or bus (if possible) to the next place.

We have carefully hand-picked 4* and 5* ‘In Style’ hotels that showcase some of the best accommodation and service this region of Tuscany has to offer, while still offering a warm welcome to hikers.

The accommodation we normally use is detailed below. In Siena, if the hotels listed are not available, then we may book you into similar standard properties, as there are several other options in the city. However, since ‘In Style’ accommodation in Gaiole in Chianti and close to the Hotel Le Fontanelle does not exist, if these hotels are unavailable then you will need to be flexible on your tour start date.

You can add on extra nights in any of the overnight locations on this tour. If time allows, we recommend adding an additional night at the end of the tour in Siena to further explore this iconic city.

Single Rooms & Solo Hikers

This trip is not available to solo hikers due to the very high price involved, as some of the costs (such as transfers) are not shared. Single rooms are available on request and a supplement is payable.

Meals

Daily breakfast and three dinners are included on this tour. The first will be at the Castello di Spaltenna where the restaurant has a 1* Michelin chef and the others during the two-night stay at the Hotel Le Fontanelle. These included dinners will be special experiences and will feature the best of Tuscan cuisine.

Lunch is not included so you are free to choose from the available options. The Macs Adventure Smartphone App gives advice on where to eat/pick up lunch on each hike.

The route is not waymarked, except for some sections on dedicated trails. However, we provide the Macs Adventure Smartphone App making it simple to follow the route using a smartphone. Rest assured that by downloading the route maps in our app, that this will continue to work even in areas without any mobile or internet reception.

This trip is available to start anytime between April 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 hiking 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 Gaiole in Chianti and includes a transfer to your hotel from Siena (takes approx. 40min).

To reach Siena, we recommend flying into Pisa Airport (PSA) or Rome Airports (FCO or CIA). There is also an airport in Florence (FLR), however flights in and out of this airport are limited.

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 Siena leave around every 30 mins, with one change and the journey takes approx. 1H45.

If arriving in Rome (note Rome has two airports): From Rome Fiumicino Airport (FCO), take the Leonardo Express Train that’s located inside the airport and departs every 15min to the central train station Roma Termini (takes about 32min). From Ciampino Airport (CIA), there’s a bus to Roma Termini (takes about 40min). From Rome’s Roma Termini Train Station, trains to Siena leave around every hour and the journey takes approx. 3H30.

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 a train to Siena takes about 1H30. Some trains are direct others go via Empoli.

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.

One main bag of up to 20kg/44lbs per person will be transferred from each accommodation to the next.