Self Guided Walking Holidays & Cycling Holidays

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Florence to Siena Self Guided Walking Holiday


  • Exploring romantic Florence, cradle of the Renaissance.
  • Walking through the vineyard cloaked hills of Chianti.
  • Enjoying the lively atmosphere of an outdoor table on the piazza.
  • The serious business of food, wine and olive oil appreciation.
  • Strolling across the Piazza del Campo in Siena.

Discover the magic of Chianti; old farmhouses, medieval villages, rows of cypress trees, quiet forests of oak, beach and chestnut, the lively atmosphere of an outside table on the piazza and the cherry flavours of a glass of Chianti Classico. This is the definitive Tuscany!

Begin with two nights in Florence, the cradle of the Renaissance; romantic, intriguing and utterly beguiling. Explore the Etruscan and Roman ruins in Fiesole. Indulge yourself in the enotecas and picture perfect landscapes of Greve in Chianti. Walk through vineyards and medieval hamlets to Radda in Chianti. Stroll through the Piazza del Campo in Siena.

The very best way to discover the secrets of Chianti is on foot. Your walking holiday in Chianti includes hand-picked 3 * superior and 4 star charming hotels, all breakfasts, luggage transfers, private transfers as per your itinerary, comprehensive route notes and maps and a detailed pre-departure information pack and emergency support.

Read one writer's tale of his experience walking from Florence to Siena in Scotland's Herald newspaper: "What a pleasure it is, therefore, to slow everything down to walking
pace, literally, and enjoy the sights, smells and tastes....
meandering through the beautiful and captivating landscape of Tuscany."

DAY 1: Arrive Florence

Settle into your accommodation and then throw yourself into the delights of Florence. Priceless renaissance art, magnificent piazzas, narrow streets, the Ponte Vecchio over the River Arno and the designer shops, will have you wishing you had more time to explore.

Overnight: Hotel Park Palace****, Florence

Minutes away, and enjoying wonderful views of, the historic centre of Florence. The Hotel Park Palace is your Florentine Villa.

DAY 2: Settignano to Fiesole

A 25 minute local bus ride brings you to the village of Settignano, where your walk begins. A typical Tuscan landscape of olive groves, cypress trees and renaissance villas unrolls before you, with the city of Florence at your feet.

Fiesole, founded in the 7th century BC, boasts Etruscan ruins, Roman baths and amphitheatres, a Franciscan Monastery, Tuscan Renaissance art and outstanding restaurants. You've a choice of walks today.

Walk 1: 8 km | 347m Ascent 224m Descent | 3 hrs

Walk 2: 14 km | 463m Ascent 463m Descent | 6 hrs

Overnight: Florence

DAY 3: Greve in Chianti Circular Walk

After breakfast, a private transfer will take you to Greve in Chianti, a rustic market village in the heart of the Chianti wine producing region.

Check into your hotel and head over to Le Cantine di Greve where you can taste over 50 different Chianti wines.  In the afternoon, enjoy a circular walk through a picture perfect Tuscan landscape north of the town.

Overnight: Albergo del Chianti***, Greve in Chianti

Located in an old tower on the main square in Chianti the Albergo del Chianti is perfectly situated. The 16 rooms are located at the rear of the building and overlook a quiet courtyard swimming pool.

Walk 1 (Greve Loop via Uzzano): 11.5 km | 425m Ascent/Descent | 2.5 hrs

Walk 2 (Greve Loop via Montefioralle): 9 km | 358m Ascent/Descent | 3.5 hrs 

DAY 4: Panzano Circular Walk

Today's walk is a lovely loop walk in the classic tuscan hills surrounding the village of Panzano. Enjoy the Chianti landscape that alternates between forests and vineyards and discover ancient farmsteads along the way.

Walk: 11km | 327m Ascent /Descent | 4 hrs 

Overnight: Albergo Chianti, Greve in Chianti

DAY 5: Walk from Badiaccia Montemuro to Radda in Chianti

After breakfast, a short car transfer takes you to the highest of the Chianti hills, Monte San Michele. From Badiaccia you descend through a forested valley of century old chestnut trees and to the medieval hamlet of Volpaia, situated amongst vineyards and castles.Stop in for a glass of red at a fine Enoteca, and then continue on to Radda in Chianti.

Radda is perched atop a high hill in a comparatively rugged part of Tuscany. The Capital of the old League of Chianti, its concentric streets still surround the historic Piazza Ferrucci, where you will find the shield encrusted Palazzo Comunale.

Walk: 12-14km | 506m Ascent 668m Descent | 3-5hrs

Overnight: Hotel Palazzo San Niccolò, Radda

Located in the heart of Radda, on the Piazza Ferrucci, the Hotel Palazzo San Nicolo is a converted medieval palace dating back to 1400. Large authentically decorated rooms with a sense of place and sophisticated commuanal areas envelop you in a sense of place. This will be a highlight of your trip.

DAY 6: Radda in Chianti Circular Walk

Bask under the Tuscan sun, go for a scenic walk around the old centre of Radda in Chianti. Wind along the narrow alleyways and visit the church of Santa Maria Novella. Treat yourself by visiting a wine cellar and tasting the wine from the celebrated local vineyards.

Walk: 16km | 586m Ascent/Descent | 5 hrs

Overnight: Hotel Palazzo San Niccolò, Radda

DAY 7: Siena

After breakfast, a prearranged private transfer will take you to Siena. Siena is famous for its biannual “Palio” horse race, held in the shell-shaped Piazza del Campo.

History comes alive as you meander through the narrow streets of this enchanting city.

Overnight: Hotel Villa Liberty*** or Hotel Chiusarelli***, Siena

The recently restored Hotel Villa Liberty offers comfortable and elegant rooms only a few minutes walk from the historic centre of Siena.

DAY: 8

Your trip finishes after breakfast.

Extensions & Extra Nights

Florence and Siena both warrant additional nights. Just ask at the time of booking and we would be happy to arrange this.


We specifically choose our hotels for comfort, location and authenticity. All are three star and four star hotels, which are centrally located and offer a genuinely warm Italian welcome and real sense of place.

Accommodation Details

We will always try and accommodate you at the locations detailed in the brochure, but because of limited availability we may have to accommodate you at an alternative location of the same or better standard. We will confirm your accommodation details on confirming your reservation.

Single Rooms

Single rooms are available but attract a single supplement.

Solo Walkers

This is a great holiday for solo walkers. If you are travelling solo the holiday is slightly more expensive as some costs are not shared.


The delicious Italian food and wine available locally is undoubtedly a highlight of this holiday. The price of your holiday includes breakfast each morning. Lunch and dinner are not included so you are free to choose from the available options.


This holiday is available to start on any day from April until the end of October.

May and June are absolutely lovely and spring and early summer is a great time in Tuscany. September & October are also lovely as the vineyards change to a pallet of reds and golds. July and August can be very hot so you will have to start early to miss the heat of the day, although the towns and villages are buzzing which is great. We also suggest that if you choose to walk during the summer months you should take plenty of water, a hat and sunscreen as shade is limited on the walks.

Single Rooms & Solo Walkers

Single rooms are available but attract a single supplement  This is a great holiday for solo walkers. If you are travelling solo the holiday is slightly more expensive as some costs are not shared.

Grade and Fitness

This holiday is graded easy to moderate because the walks are relatively short and you can choose to shorten them. Tuscany is hilly and there are some steep descents and ascents so you should have suitable fitness. You will walk on city streets, dirt tracks, mule tracks and footpaths. The longest day is Day 6, with a loop walk of 16km.


The walks are generally not way marked. We supply very detailed route notes and maps so navigation is straightforward.

You will also have access to the Macs Adventure Smartphone App enabling you to follow the route using your phone’s GPS so using this combined with the provided route notes and maps means you should have no problems finding your way.

Baggage Transfer

When required your bags will be transferred from your hotel and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.

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 Florence

We recommend arriving at either Florence or Pisa Airports.

Buses and taxis from Florence Airport to the City Centre take 25 or 15 minutes respectively and cost 4.50/20 Euro).

From Pisa Airport buses/taxis connect to the station and trains to Florence take 1h30.

Direct buses from Pisa Airport to Florence (70 min) are also available.

Travelling by Car

The hotels we use do not have private parking. Parking is available in Florence and Siena and costs about 25 Euro per day.

Getting From Siena

Florence and Pisa Airports are closest. Siena has good road and rail links to all Italian destinations.


  • 7 nights accommodation including breakfast
  • Luggage transfers as per your itinerary
  • Private transfers from Settignano to Greve in Chianti (Day 3), from Greve in Chianti to Monte San Michele (Day 5) and from Radda in Chianti to Siena (Day 7)
  • 24-hour telephone assistance
  • Detailed route notes, maps and access to the Macs Adventure Smartphone App


  • All lunches & Dinners
  • Flights and public transportation
  • Bus to the village of Settignano on Day 2
  • Travel insurance
  • Admissions and entrance fees to any museums
  • Personal expenses such as wine tasting, drinks, phone calls, etc
  • Any item that has not been specifically mentioned in the program


  • Private airport transfers
  • Additional nights
  • Guided tours of Florence or Siena with private local city guide.
  • Cooking lessons in Florence or Siena

We are often asked the following questions and I hope that you will find the answers useful. Don't hesitate to contact one of our Italy specialists if you have any further queries. 

How far in advance do I need to book?

We suggest you book as soon as your plans are finalised as this area is extremely popular. You will find up to date availability on our website and we will always try and accommodate your plans so just ask.

How fit do I need to be?

This walking holiday is graded easy and involves between two and five hours of walking each day. Most of the walks can be shortened or extended as required. Some walks are totally optional. There are some steeper ascents and descents so you should enjoy a reasonable level of fitness to get the most from this holiday.

When is the best time of year?

May and June are absolutely lovely and spring and early summer is a great time in Tuscany. September & October are also lovely as the vineyards change to a pallet of reds and golds.

July and August can be very hot so you will have to start early to miss the heat of the day, although the towns and villages are buzzing which is great.

What personal equipment do I need?

You will need good walking shoes/boots, comfortable walking clothes, waterproof jacket and trousers, a daypack and hats/gloves etc.

How do the baggage transfers work?

When required your bags will be transferred from your hotel and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.

Which is the best airport?

Pisa and Florence are the best airports to fly into. Rome is also a possibility, but transfer times are longer.

Fun but much more challenging than expected


The hikes on this tour took us through some beautiful terrain. The instructions were clear and easy to follow. The paths were well-defined, uneven and rocky. We were happy that there was no rain because the paths would have been very difficult if they were wet. We would have needed poles. There was a lot of elevation change and the paths were very steep. The difficulty was much greater than advertised and we actually didn't do the "moderate" hike on our last day out of Radda because the hike rated "easy" the day before was at the height of our tolerance. We were a group of fit individuals who walk often. The views made it worth it.




Fantastic vacation in Chianti!


This is the best way to have a perfect vacation within budget with young adult children. The trips included history, culture, art, cities, crowds and remote countryside and peaceful Villages. All in one. Never a dull moment.

Lucy the mother, the romantic

New Hampshire


I would choose a different Macs tour


We enjoyed this trip. The towns and cities of Tuscany were well chosen. The countryside was beautiful. The unfortunate thing was that the wineries were not all open due to the early date. It might be good to put that information into the trip notes. Otherwise we were totally satisfied with all arrangements before and during our trip.

The 4 intrepids

North Scotland


Well organised trip


Accommodation and track information was great. The towns we stayed in were interesting. The walking was varied, at times strenuous but with many rewarding views. A good mix of local forests, vineyards and orchards. We were lucky that the weather was mild, it would be a very hot route in summer as you are often in the open. Overall, a great experience in a lovely part of Italy.


Shoalhaven, NSW, Australia


A memorable trip


Given that this walk starts in one of the most important cities of the Renaissance we preferred to spend what limited time we had in the centre rather than on the outskirts at Fiesole


Sydney Australia


Very Smooth!


I like to use a walking tour as a way of seeing a locale that is more personal and engaging than the traditional guided-tour-bus kind of trip. This was my first Mac's Adventure trip and I was very impressed with the accommodations and the overall organization. Everyone who was scheduled to take me and/or my luggage to the next spot showed up on time, and everything went very smoothly.

Virginia the Retired Teacher

Idaho, USA


Sample Chianti wines after walking through the vineyards


Having done the Amalfi coast, the walks were not as dramatic and often through forest. Views are wonderful of rolling Tuscany hills and villages. This holiday is more about the charm of Chianti and the impact of the beautiful cities of Florence and Siena. To make the most of this holiday sample the wines and cheeses at the vineyards you pass by. The Italians keep the best wine to themselves and we did not have a bad one while we were there. It was unseasonably hot in the Sept week(31degrees) so we were pretty hot and bothered by the time we reached some of the villages. Also the mosquitoes were out in force so bring plenty of repellant. Usually by mid September they will be gone but we were unlucky. Overall it was a wonderful Tuscany experience with nice hotels (all clean with comfy beds) and fabulous eating. Go with friends as we did and enjoy La Dolce Vita.






Very well organised with a variety of walks interspersed with sightseeing in villages, towns and cities.

Summer Wine

Holmfirth, Huddersfield West Yorkshire


What an adventure


This is an amazing trip where you stay in great accomodation, see amazing scenery, enjoy fantastic local food and wine and get some exercise along the way. Some days are longer and more tiring than other but in all it's fantastic.




A wonderful trip to Tuscany.


All the documents were very good. It took some time to notice the marking on the trees on the first walk from Settignano - Fiesole. We did not know where to look for the red/ white markings. It would be better to put the marking in the guide, as it looks :)


Kopavogur Iceland


Tuscany: From Florence to Siena

4.5 20


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