Self Guided Walking Holidays & Cycling Holidays

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Timeless landscapes of Chianti


  • 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.

Day 1: Arrive in Radda in Chianti and overnight

What better way to begin your Classic Chianti tour 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.

Walk: 13 km

Overnight: Radda in Chianti

Day 3: Walk to Gaiole in Chianti via Vertine

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 delightful B&B.

Walk: 14 km

Overnight: Gaiole in Chianti

Day 4: Gaiole in Chianti Loop Walk via 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 you may visit and have a wine tasting (not open on Sundays). 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 the 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 Lecchi in Chianti

 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.

Walk to Lecchi in Chianti, a quaint, stone village that has origins dating back to the medieval age. Several characteristics from this period, such as it's narrow alleyways ,can be seen and this offers a lovely and ancient atmosphere.

Walk: 10 km

Overnight: Lecchi in Chianti

Day 6: Walk to Siena

Transfer to the delightful hamlet of San Sano and then make your way on foot to Siena. 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.

Day 7: Free Day in Siena

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: 20 km

Overnight: Siena

Day 8: Onward journey

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


7 Nights 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.

The accommodation we normally use is detailed below. However we may use alternatives ion a similar standard should the dates you request not be available.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.


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.




Palazzo San Niccolo

This hotel is located in the old centre of Radda in Chianti in an ancient and beautiful building. The charming rooms have all modern comforts.




Cavarchino B&B - Gaiole in Chianti

This adorable B&B on the outskirts of Gaiole in Chianti has great views. It is located within a restored stone farmhouse and at the end of your walk you can relax by the outdoor pool.







Le Pozzi di Lecchi - Lecchi-in-Chianti

Located in a very quiet environment in the heart of the Chianti region, Hotel Le Pozze di Lecchi offers two outdoor pools with panoramic views over the Tuscan hills and vineyards. The rooms are fully equipped with air conditioning.







Hotel Alma Domus - Siena

Hotel Alma Domus enjoys the privilege of being in the heart of Siena’s historic city centre. Many of the rooms have balconies over looking city views and they are all stylishly decorated.








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.

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.


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.

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.

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 and from Siena

By Air: 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.


  • 7 Nights in good quality B&B’s, 3 and 4* hotels
  • 7 Breakfasts
  • Baggage transfers
  • Transfer from Siena to Radda in Chianti (Day 1)
  • Transfer from Lecchi in Chianti to San Sano (Day 6)
  • Route notes, maps and detailed information pack
  • Access to the Macs Smartphone App
  • 24-7 Emergency telephone support.


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


  • Additional nights before, during or after the walk
  • Single room supplement if required
  • Solo Walker Supplement

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.

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. We advise that if you want to travel during these months that you start out on your walks early, so avoiding the midday heat.

Beautiful Trip!


Overall really loved this tour. Walk on a lot of roads vs nature paths. But scenery is so beautiful.

Amy R

South Carolina


I would go again.


Everything was fine, some very nice hotels and the hikes were manageable. Someone might do well to double-check the route directions, since occasionally right and left are confused, leading to unnecessary backtracking.


Wetzikon, Switzerland


Tuscany: Classic Chianti

4.0 2


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