Classic Chianti

Tour Style:

Self Guided | Go at your own pace on an independent active trip.

Activity:

Multi Center Walking | You will spend multiple nights in one or more of the locations on this walking tour

Activity Level & Terrain

This trip is graded ‘moderate’ overall, as the terrain is somewhat hilly. You should therefore be in good physical fitness to fully enjoy the walking on this tour. Most of the route follows gravel and farm tracks and trails, and you will also be following minor roads from time to time. You’ll be walking an average of 14-15 km each day and any loop walks on our longer itineraries are optional. Should you wish to skip a walk between towns then you will be responsible for taking a taxi or bus (if possible) to the next place.

Navigation

The route is not waymarked (with the exception of some sections where you will be walking dedicated trails). Detailed routes note and GPS data will be provided for you via the Macs Adventure App. Further information will be provided upon receipt of your booking.

• Overnights in hand-picked accommodations
• Breakfast included
• Baggage transfers
• Transfers as per itinerary
• Route notes, maps and detailed information pack
• Access to the Macs Smartphone App
• 24-7 Emergency telephone support

• Travel insurance (required)
• Travel to starting point/from finish point
• Lunches & dinners
• Drinks and snacks
• Personal equipment

• Additional nights before, during or after the trip

When To Go

You can start this walking tour anytime between April and October. Please bear in mind that July and August can be very hot for walking. We advise that if you choose to walk during these months that you begin the walks very early in the morning, so as to avoid the midday heat. Availability in Siena is very difficult around the times of the 'Palio' horse races held each year.

Getting to the Start

On this tour an included transfer will bring you from Siena to Radda-in-Chianti, your starting point. 

In order to reach Siena you can fly into Pisa or Rome Airports. There is also an airport in Florence, however flights in and out of this airport are limited.

From Pisa you can take a special “people mover” from the airport to the Pisa Centrale Train Station and then a train to Siena. They leave every 30 mins, with one change and the journey takes approximately 1H45. From Rome you can take a Leonardo Express Train into Rome centre and then a train to Siena (however you have to go to Florence, then change). The trains leave approximately every hour and the journey will take approximately 3H30. From Florence you can take a train to Siena. The journey time is about 1H30. Some trains are direct whereas on others you will have to change in Empoli.

Please check the Trenitalia website for timetable planning.

Getting from the End

As the tour finishes in Siena, you can use the same travel information as in Getting to the Start.

Luggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 50 lbs. per person.

General Information

Cooking Class

The cooking lesson on the second day of this trip takes place in Palazzo Leopoldo’s original ancient kitchen, for a truly authentic Tuscan experience. The cooking lesson begins around 5:00 PM and lasts for about 4-5 hours, ending with dinner derived from the meals made during the course. The meal prepared consists of a 4-course menu, using traditional recipe's and seasonal ingredients. Please let us know at the time of booking if you have any particular preferences, intolerances or food allergies so that we may personalize the menu for you in advance.

Wine Tour & Tasting

The wine tour and tasting on the fourth day of this trip takes place at the Riecine Winery (about 1.5 miles from Gaiole). The tour and tasting begins at 10:30 AM at the entrance to the winery, where your friendly hosts will greet you and take you on a tour of the winery and vineyards (approx. 1 hour). Enjoy learning all about the history, grapes and methods, followed by a tasting, before continuing on with your day’s walk.  For more information about the winery check the Riecine Winery website.

Please note that tours are only offered after Easter and are closed on Sundays. Please check your dates before booking to avoid any conflicts with this tour.

Equipment

Our pre-departure information pack has  detailed advice and a packing list on what to bring. This includes warm and cold walking gear, hiking boots, rain gear, day pack and other specifics.

Travel Insurance

Travel insurance helps protect your travel investment, your belongings and most importantly you, from unforeseen circumstances that may arise before or during your trip. For more information, please visit our travel insurance page.