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Florence to Siena

8 Days & 7 Nights 4.5 Read 25 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 Style:

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


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

This trip is suitable for:

Solo Travelers, Multi-Generational

As a guide, we would suggest that the minimum age of traveler this tour would be suitable for is: 5 Years

Ideal if you have an interest in:

  • Foodie Adventures
  • Wine, Whiskey & More...
  • Historical Journeys

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 (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.


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 trip

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 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.

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

Cooking Class

The cooking lesson on the second day of this trip takes place in Palazzo Leopoldo’s original ancient kitchen, for a truly authentic Tuscan experience. The cooking lesson begins around 5:00 PM and lasts for about 4-5 hours, ending with dinner derived from the meals made during the course. The meal prepared consists of a 4-course menu, using traditional recipe's and seasonal ingredients. Please let us know at the time of booking if you have any particular preferences, intolerances or food allergies so that we may personalize the menu for you in advance.

Wine Tour & Tasting

The wine tour and tasting on the fourth day of this trip takes place at the Riecine Winery (about 1.5 miles from Gaiole). The tour and tasting begins at 10:30 AM at the entrance to the winery, where your friendly hosts will greet you and take you on a tour of the winery and vineyards (approx. 1 hour). Enjoy learning all about the history, grapes and methods, followed by a tasting, before continuing on with your day’s walk.  For more information about the winery check the Riecine Winery website.

Please note that tours are only offered after Easter and are closed on Sundays. Please check your dates before booking to avoid any conflicts with this tour.


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.

When is the best time of year?
What personal equipment do I need?
How fit do I need to be?
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 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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