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Chianti In Style

7 Days & 6 Nights 4.7 Read 3 reviews
  • Walk on Tuscany's Chianti Classico wine routes
  • Outstanding 4* & 5* hotels in exquisite locations
  • Chianti wine tour and tasting at one of the finest vineyards in the region
  • Enter the glorious medieval city of Siena on foot, a Gothic open-air museum
  • Sample Tuscan flavours during dinner at a Michelin star restaurant
Walk Tuscan wine trails through the timeless landscapes of Chianti to Siena, staying in ‘In Style’ accommodation. This very special tour combines walking with opportunities to eat authentic Tuscan cuisine at a Michelin star restaurant, tour a vineyard and of course sample the world-renowned wines, and stay in the outstanding hotels. An intoxicating mix of exceptional experiences. This alluring region has been producing world-famous velvety red wines since the 13th century. Situated between Florence and Siena, Chianti, is formed of castles, fortresses, Romanesque churches, olive groves, and row upon row of vines, interspersed with pretty wooded valleys.

What To Expect

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 walking, and on this tour, you take ‘easy to moderate’ graded walks following trails through classic Chianti landscapes where time has stood still. There are numerous ascents/descents on the walks, due to the nature of the undulating Tuscan scenery. If time allows, we’d 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.

Trip Type:

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&B’s, inns, and guesthouses.

Ideal if you have an interest in:

Foodie, Wine

As a guide, we would suggest that the minimum age of traveller this holiday would be suitable for is: 12 Years

Grade & Terrain

This trip is graded ‘easy to moderate’ overall. The terrain is undulating with regular ascents and descents, and summer temperatures can be high. 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 minor roads from time to time. It’s best ahead of time to do some practice walks including stairs and ascents and descents like those you will experience on the trip whilst carrying your day bag. The walks are an average of 15-16 kms 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 walk between towns then you will be responsible for taking a taxi or bus (if possible) to the next place.


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. For extra reassurance there are also turn-by-turn route notes within the app too for the walks.

Accommodation Information

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, whilst still offering a warm welcome to walkers.

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, then we would recommend adding an additional night at the end of the tour in Siena to further explore this iconic city.

Single Rooms & Solo Walkers

This trip is not available to solo walkers 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.


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 walk.

  • Accommodation in en suite rooms in 4* and 5* hotels on a double share basis
  • Daily breakfasts
  • Three dinners including one in a 1* Michelin restaurant with wine
  • Wine tour and tasting
  • Transfers as per your itinerary
  • Door to door baggage transfers as per your itinerary
  • All your trip documents including a detailed information pack provided digitally through your online Macs “My Account”
  • Access to maps, GPX tracks and daily route information with the Macs Adventure smartphone navigation app
  • Telephone support from our offices in the event of a problem
  • Travel insurance (required) and personal equipment
  • Lunches, other dinners, drinks, and snacks
  • Tourist taxes (charged locally at hotels)
  • Travel to and from Siena
  • Any additional transfers or public transport required to shorten the walks or skip a stage
  • Additional nights before, during or after the tour
  • Private transfer from the end point of the tour to the airport
  • Room upgrades

When To Go

This tour 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 difficult around the times of the 'Palio' horse races held annually normally in early July and then again in mid-August.

Time of Year

The springs months of April, May and June offer warm sunshine, fewer crowds, and pleasant walking conditions. May is when most wildflowers are coming into bloom. The autumn months of September and October are also a favourable time of year, boasting cooler weather and a striking landscape made up of autumnal colours. 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. Although the towns and villages are buzzing at this time of year which is great to see.

Getting to the Start

On this tour an included transfer will bring you from Siena train station to Gaiole in Chianti, the starting point. The drive is around 40 minutes.

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

If arriving at Pisa from the airport take the PisaMover to the main train station (takes 5 minutes). Turn left when exiting arrivals and the PisaMover is at the end of the airport. From Pisa Centrale Train Station trains to Siena leave around every 30 mins, with one change and the journey takes approximately 1 hour 45.

Rome has two airports. From Fiumicino Airport take a train to the central station Roma Termini (taking about 30 minutes). From Ciampino Airport there’s a bus to Roma Termini. From Rome centre change trains in Florence to go to Siena. Trains leave approximately every hour and take about 3 hours 30.

If landing at Florence Airport, there’s a shuttlebus into the centre of Florence (taking around 25 minutes). It stops beside the main railway station of Santa Maria Novella. From Florence a train to Siena takes about 1 hour 30. Some trains are direct whereas 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.

Getting from the End

As the tour finishes in Siena, use the same travel information as shown in ‘Getting to the Start’ to reverse the journey back to the chosen departure point.

Baggage Transfer

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

General Information


Our pre-departure information pack details 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. 

How fit do I need to be?
How far in advance do I need to book?
What personal equipment do I need?
When is the best time of year?
Which is the best airport?
How does the luggage transfers work?


Day 1 Arrive in Siena; transfer to Gaiole in Chianti Day 2 Transfer to Radda; walk back to Gaiole in Chianti via Vertine 9 miles / 14 km Day 3 Gaiole in Chianti Loop Walk via Badia a Coltibuono Monastery & Riecine Winery 9 miles / 15 km Day 4 Walk to Hotel Le Fontanelle, near Pianella 11 miles / 18 km Day 5 Free day at Hotel Le Fontanelle Day 6 Walk to Siena 9 miles / 15 km Day 7 Onward travel from Siena

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