Classic Chianti: Florence to Siena

8 Days & 7 Nights 4.5 Read 26 reviews
  • Explore Florence and Siena combined with sublime walking in Tuscany's Chianti
  • Timeless landscapes of vineyards, olive groves and cypresses
  • Sample the premium, world-class wines of the region, such as Montalbano
  • Hike into the glorious medieval city of Siena, a Gothic open-air museum
  • Hand-picked accommodations all in enchanting locations
Discover the magic of Tuscany on this wonderful walking tour. Beguiling Florence, the Cradle of the Renaissance, medieval Siena, a UNESCO World Heritage Site and sublime walking in the Chianti region. Wander through beloved Tuscan landscapes and an intoxicating mix of serene scenery; quiet forests, pretty wooded valleys, row upon row of vineyards and iconic cypress trees, small hamlets and old farmhouses. This unforgettable getaway under the Tuscan sun has a plethora of highlights. Take a walking tour of Florence, a city of timeless beauty. See Michelangelo's David in the Uffizi and the stunning Duomo. At the end of your walking day sample the world-famous and full-bodied Chianti wines and spend your overnights in hand-picked accommodations all in glorious locations.
On this tour not only will you have the chance to explore the two great medieval cities of Florence and Siena, but you will also take moderate walks following trails through classic and timeless Chianti landscapes. 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.

Tour Type:

Slower Adventures | Where walking and cycling meet easy-going exploring, our Slower Adventures are the perfect combination. Most days are filled with picturesque journeys with some free time to dive into the destination and experience the people, local food and culture as you go.


Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&B’s, inns, and guesthouses.

This trip is suitable for:

Solo Travellers

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

Ideal if you have an interest in:

  • Foodie
  • Wine

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.


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.


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


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.

  • 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 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

In order to reach Florence, 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 Florence, you can reach the city centre by train or bus within 15 minutes. From Pisa, you can take a special “people mover” from the airport to the Pisa Centrale Train Station and then a train to Florence. They leave every 30 mins and the journey takes approximately 1H15. From Rome, you can take a Leonardo Express Train into Rome centre and then a train to Florence. They leave frequently and the journey will take approximately 2H.

Please check the Trenitalia website for timetable planning.

Getting from the End

Your finishing point is Siena. You can fly from Pisa or Rome Airports. There is also an airport in Florence, however, flights in and out of this airport are limited.

From Siena to Florence, you can easily take a train to Florence and then another train to the airport. From Siena to Pisa you can a train to Pisa Centrale Train Station and then a special “people mover” to the airport. Trains leave every 30 mins, with one change and the journey takes approximately 1H45. You can also fly from Rome which is slightly more complicated as you have to take a train from Siena to Florence and then change for a train to Rome. The trains leave very frequently however and the total journey takes about 3H30, depending on how many stops. From central Rome, you can take a Leonardo Express Train to Rome Fiumicino airport.

Please check the Trenitalia website for timetable planning.

Luggage 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.

General Information

Please note that the reviews for this walking holiday up until December 2019 are based on our previous itinerary. As of December 2019, minor changes and improvements have been made to enhance your experience.


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 Florence and overnight Day 2 Walking tour of Florence (self-guided). Free afternoon 4 miles / 6 km Day 3 Private transfer to Radda in Chianti. Radda in Chianti Loop Walk via Castelvecchi & Volpaia Vineyard 8 miles / 13 km Day 4 Walk to Gaiole in Chianti via Vertine 9 miles / 14 km Day 5 Gaiole in Chianti Loop Walk via Badia a Coltibuono Monastery & Riecine Winery 9 miles / 15 km Day 6 Walk to Lecchi in Chianti 6 miles / 10 km Day 7 Transfer to San Sano. Walk to Siena 12 miles / 20 km Day 7: Onward Travel

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