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Classic Chianti

8 Days & 7 Nights 4 Read 2 reviews
  • Walk on classic wine routes from Radda in Chianti to Siena
  • Hand-picked accommodations, all in sublime locations
  • In the heart of Chianti, sample the premium, world-class wines
  • Hike into the glorious medieval city of Siena, a Gothic open-air museum
  • Timeless and classic landscapes of vineyards, olive groves and cypresses
Follow Tuscan trails through the unforgettable wine region of Chianti to Siena, whose historic centre is a UNESCO World Heritage Site. This tour is an intoxicating mix of exceptional experiences as you walk from village to village through this striking region of Chianti. Known as Tuscany’s “third” city, after Florence and Siena, it is formed of castles, fortresses, Romanesque Churches, olive groves and row upon row of vines, interspersed with pretty wooded valleys. This alluring region has been producing world-famous velvety red wines since the 13th century and there will be plenty of opportunities during your walks to visit local vineyards and to enjoy some wine-tasting.

What To Expect

On this tour you will take moderate walks following trails through classic and timeless Chianti landscapes. You will stay in hand-picked accommodations in great locations, with many chances to visit vineyards along the way. Everywhere you walk you will enjoy fantastic views and great local hospitality.

Trip Style:

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

Activity:

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

This trip is suitable for:

Multi-Generational

Ideal if you have an interest in:

  • Foodie Adventures
  • Wine, Whisky & More...
  • Wellness & Spa

Grade & 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.

Accommodation Information

Stay in good quality B&B’s, 3* and 4* hotels, all located in glorious settings, be it a town, a hamlet or the wonderful city of Siena.

You can add on extra nights in any of the overnight locations on this tour.

Solo Walkers & Single Rooms

This trip is available to solo walkers, although there is a supplement due to the fact that some of the costs (such as transfers) are not shared. Single rooms are available on request and a supplement is payable.

Meals

A breakfast will be provided by your accommodation every morning. Usually they are buffet-style or continental breakfasts. Dinners are not included, however there are options to dine out in any of the towns, villages and many, many options in Siena.

Lunches are also not included, but you can find small stores in which to purchase items for a picnic lunch, or your accommodation can possibly make a picnic lunch if you ask in advance. In your route notes we give advice on where you can eat/pick up lunch.

Included
  • 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.
Excluded
  • Travel insurance (required)
  • Travel to starting point/from finish point
  • Lunches & selected dinners
  • Drinks and snacks
  • Personal equipment
Extras
  • Additional nights before, during or after the walk

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 therefore advise that if you choose to walk during these months that you begin the walks very early in the morning, so to avoid the midday heat. 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

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.

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 20 kg 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. 

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

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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Itinerary

Day 1 Arrive in Radda in Chianti and overnight Day 2 Radda in Chianti Loop Walk via Castelvecchi and Volpaia Vineyards 8 miles / 13 km Day 3 Walk to Gaiole in Chianti via Vertine 9 miles / 14 km Day 4 Gaiole in Chianti Loop Walk via Badia a Coltibuono Monastery 9 miles / 15 km Day 5 Walk to Lecchi in Chianti 6 miles / 10 km Day 6 Transfer to San Sano, walk to Siena 12 miles / 20 km Day 7 Free Day in Siena Day 8 Onward Travel

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