Self-Guided Walking Tours & Biking Tours

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Timeless and stunning while walking in Tuscany's Chianti


  • Walk in style on Tuscany's Chianti Classico wine routes
  • Outstanding 4* & 5* hotels in exquisite locations
  • Chianti wine tour & tasting
  • Hike into the glorious medieval city of Siena, a Gothic open-air museum
  • A traditional cooking class in the ancient kitchen of the Palazzo Leopoldo

Walk Tuscan wine trails through the timeless landscapes of Chianti to Siena, staying in luxury accommodations.

This very special tour combines perfect walking and opportunities to eat and learn to cook authentic Tuscan food with touring a vineyard and stays in the finest premium 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, known as Tuscany’s “third city”, is formed of castles, fortresses, Romanesque Churches, olive groves and row upon row of vines, interspersed with pretty wooded valleys.

Day 1: Arrive Siena, transfer to Radda in Chianti and overnight

What better way to begin your Chianti tour in luxury than with 2 nights in the Medieval wine town of Radda in Chianti, perched on a hilltop and surrounded by the stunning landscapes of the region. Siena is easily accessible from Pisa Airport (1H45) and from here a transfer to Radda is included.

Tonight celebrate the beginning of your tour by selecting a delightful restaurant in which to eat some homemade pasta and enjoy a glass of the world famous red wine, Chianti Classico.

Overnight: Radda in Chianti

Day 2: Radda in Chianti Loop Walk via Castelvecchi & Volpaia Vineyards

Walk directly out of town from your hotel and you will immediately be immersed within famed Chianti vineyards. Walk uphill to Castelvecchi, where there is a vineyard on top of the rise and where you will also pass the Church of Pieve di Santa Maria Novella. Take a small wooded trail which comes out to full views of the valley and arrive in Volpaia, an adorable hamlet, with a winery and a café that serves delicious lunches in the piazza.

Walk through rows of cypress trees until Radda comes into view again. It’s an uphill walk the last few hundred metres, but feel exhilarated when you arrive back to your 4* hotel where you can relax in the spa if you wish.

This evening enjoy a cooking class in the old kitchen of the hotel with 3 sisters, Anita, Valentina and Rosanna who will take 4-5 hours to show you how to cook simple and rustic Chiantigiane cuisine.

Walk: 13 km

Dinner & Overnight: Radda in Chianti

Day 3: Walk to Gaiole in Chianti via Vertine

After a delicious breakfast made in the ancient kitchen where you had your cooking class last night, set off on today’s walk which will take you through a dense concentration of vineyards, olive groves, orchards, terraced slopes and wooded valleys.

Reach Vertine a hamlet with a castle and medieval walls. Inside these walls see the Church of San Bartolomeo a Vertine, dating back to the 11th century. Inside you can admire part of the Renaissance frescoes by the Florentine school. Vertine also has a winery if you care to stop for some wine tasting.

Walk downhill into Gaiole in Chianti and to your amazing 5* hotel located in a castle with stunning views. Enjoy dinner tonight in its 1* Michelin restaurant!

Walk: 14 km

Dinner & Overnight: Gaiole in Chianti

Day 4: Gaiole in Chianti Loop Walk via  Riecine Winery (with wine tour & tasting) & Badia a Coltibuono Monastery

This walk reveals the variety of Chianti landscapes as it takes you through both woods, vineyards and olive groves.  About 1.5 km out of Gaiole you will pass the Riecine Winery where a wine tour & tasting has been arranged for you. At this winery there have been generations of winemakers since Etruscan times and their objective is to create the very best wines from Sangiovese, the indigenous grape of our Chianti Classico region.

Then, continue on your walk through the lovely little hamlet of Montegrossi and to the stunning monastery of Badia a Coltibuono,  Monks took over this monastery in the 12th century and established a tradition of expert viticulture.

Walk: 15 km

Overnight: Gaiole in Chianti

Day 5: Walk to Hotel Le Fontanelle

After a sumptuous breakfast on the beautiful terrace of the Castello di Spaltenna, begin today’s walk. Two thirds of Chianti’s 70,000 hectares are still covered in oak woods and boar, hares, deer and pheasants still live in these locales. You may be lucky enough to spot one of these wild animals en route.

As you approach see Hotel Le Fontanelle up on a ridge. It is a restored 13th century property and in a very special locale with views all around. We suggest departing from Gaiole-in Chianti early so that you have time to make the most of your stay at this idyllic hotel, with its outdoor & indoor pool, botanic garden, sauna, whirlpool and steam bath.

Walk: 17 km

Dinner & Overnight: Hotel Le Fontanelle

Day 6: Walk to Siena

Leave the lovely Hotel Le Fontanelle on foot and make the most of your last day of walking through these pristine and timeless landscapes. As you approach Siena you will walk past the Basilicata dell’Osservanza from where there are fantastic views over this glorious Medieval city.

This city is famous for the Piazza del Campo which is at the very core of the city and shaped like a scallop-shell. It is also the setting for the famous Palio horse race.  

Walk: 15 km

Overnight: Siena

Day 7: Onward journey

Take your onward journeys by train to Pisa (1H45), Florence (1H30) or Rome (3H30).


6 Nights luxury accommodation is included in your trip. We’ve carefully hand-picked  4* and 5* properties and they are the best that this region of Tuscany has to offer.

The accommodation we normally use is detailed below. In Radda in Chianti and Siena, if the hotels listed are not available, then we may book you into similar standard properties. However since luxury accommodation in Gaiole in Chianti and close to the Hotel Le Fontanelle does not exist you may need to be flexible on your tour start date.

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

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.


3 Dinners are included as part of your tour. The first will be part of the cooking class at Palazzo Leopoldo on Night 2. Another dinner will be included on Night 3 at the Castello di Spaltenna where the restaurant has a 1* Michelin chef. The 3rd will be at the Hotel Le Fontanelle. All of the dinners will include wine. These included dinners will be special experiences and will feature the best of Tuscan cuisine.

The price of your tour also includes breakfast each morning.  Lunch is  not included so you are free to choose from the available options. In your route notes we give advice on where you can eat/pick up lunch.



Palazzo Leopoldo - Radda in Chianti

Nestled in the expanses of the vineyards of Chianti, Palazzo Leopoldo is set in an enchanting building originally built in the 1300’s. It retains its original structure both inside and out.







Castella di Spaltenna - Gaiole in Chianti

This exquisite 5* hotel is set in an ancient monastery from the 10th century. The large rooms have traditional Tuscan décor and panoramic views over the valley or the courtyard.







Hotel Le Fontanelle - Pianella

This very beautiful resort was a 13th century house that has been lovingly restored. It is set in the middle of the gorgeous Chianti countryside and is located on a hill so has fantastic views.







Relais degli Angeli - Siena

Right in the heart of Siena, this exceptional and elegant period residence offers a special stay and a very warm welcome.








You can start this walking tour anytime between April and October.  Please bear in mind that July and August can be 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 as 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.

Please note that the wine tour and tasting is not available on Sunday’s so try to avoid beginning your tour on a Thursday if possible.

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.

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 on 2 days the loop walks 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, Route Notes & Maps

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.

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 20kg per person.

Cooking Class

The cooking lesson in Palazzo Leopoldo takes place in the original ancient kitchen of the hotel. You will prepare a 4-course menu and the traditional food that will be cooked will depend on the season, in order to offer the most fresh ingredients. Moreover, at the time of booking you can let us know what is to your particular taste so that you may have a personalized menu. They also accommodate vegetarians and people with food intolerances or allergies. The cooking lesson begins at 5:00 pm, lasts for 4-5H and ends with dinner (eating the dishes that you made during the course) and a good Chianti Classico wine.

Wine Tour & Tasting

This will be organised on Day 4. You walk past the Riecine Winery about 1.5-2km from Gaiole. The tour and tasting is booked for 10:30am. Your friendly wine hosts will take you on a tour of the vineyard, which will take about 1 hour You will then continue on with today’s walk. For more information about the winery check the Riecine Winery website.

Please note that the winery is closed on Sunday’s. Therefore if your tour begins on a Thursday you will be unable to have the tour. Also they only offer tours after Easter so please check your dates before booking.

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.

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. 

Getting to Radda in Chianti

Included in this trip is a private transfer from Siena to Radda in Chianti (Day 1).

Getting to Siena

Air & Train

To get to Siena, Pisa and Florence both have airports with flights from international and national destinations.

We recommend flying into Florence and taking a taxi from the airport to the Florence Train Station. Trains to Siena from Florence depart several times per day (approx. 2 hours total, note—some trains are direct while others have a change over in Empoli).

If flying into Pisa, take the tram from the airport to the Pisa Centrale Train Station. Trains to Siena leave from Pisa Centrale Train Station every 30 minutes (approx. 2 hours total, including one change over along the route).

Getting from Siena

By Train:

Trains to Florence, Pisa and Rome depart everyday directly from Siena Train Station. Trains, ticketing and more information can be found within your pre-departure information pack. For additional information, please check the Trenitalia website for updated timetables.



  • 6 Nights in 4* and 5* luxury hotels
  • 6 Breakfasts
  • 3 Dinners (wine included and one in a 1* Michelin restaurant)
  • Baggage transfers
  • Taxi transfer from Siena to Radda in Chianti on Day 1
  • Cooking Class (4-5H)
  • Wine Tour & Tasting
  • Route notes, maps and detailed information pack
  • 24-7 Emergency telephone support.


  • Travel insurance (required)
  • Travel to and from Siena
  • Lunches & 3 Dinners
  • Drinks and snacks
  • Personal equipment


  • Additional nights before, during or after the trip
  • Single room supplement (if required)
  • Solo supplement (if required)

We are often asked the following questions and we hope that you will find the answers useful.

How fit do I need to be?

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.

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised as the region is extremely popular. 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.

Please note that the wine tour and tasting is not available on Sunday’s so try to avoid beginning your tour on a Thursday if possible.

What personal equipment do I need?

You will need good walking shoes/boots (ideally waterproof), comfortable walking clothes, and dependent on when you are travelling; waterproof jacket and trousers, a daypack and hats/gloves etc. Our info packs have a list of all equipment to bring on your walk.

When is the best time of year?

If you prefer to walk in cooler months then May, June and September/October will be perfect for you. The autumnal colours are spectacular in Tuscany.  The summer months (July, August) can be very hot.

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