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Self Guided Walking Holidays & Cycling Holidays 

Tuscany: From Florence to 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.


Highlights

  • 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.

DAY 1: Arrive Florence

We recommend flying to Florence (30 min) or Pisa (2 hours).


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 (4 Star)


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


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.


Walk: 7 km | 300m Ascent 100m Descent | 2.5 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 (3 Star).


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. Website: www.albergodelchianti.it


Walk: 11 km | 300m Ascent/Descent | 3.5 Hours


DAY 4 Walk from Greve to Panzano

Todays walk is to the fortified village of Panzano. Walking in a near perfect landscape of medieval castles, fortified hamlets and Tuscan farmhouses surrounded by cascading vineyards.


Walk: 6km | 250m Ascent 30m Descent | 2 Hrs


Overnight: 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: 11km | 450m Ascent 350 Descent | 4.5Hrs


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. Website: www.hotelsanniccolo.com


DAY 6 Radda in Chianti Circular Walk

A quiet, relaxing day awaits you. 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: 7km | 250m Ascent/Descent | 2.5 Hours


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 (3 Star), Siena.


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


DAY 8

Onward Travel


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.

Accommodation

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.


Meals

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.


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.


Equipment

Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, waterproofs, comfortable walking clothes, warm and waterproof clothes and a day pack.


Walking Grade

This holiday is graded easy because the walks are relatively short and you can choose to shorten or skip them as you wish. 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.


Navigation

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

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.

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 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.

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.

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.

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.


This walking holiday is available from April to October. You can start your holiday on any date in the season. To make a provisional reservation select "Book" for the itinerary you are interested in.


The pice does increase in high season (August to October). 


Optional Extra prices will be displayed as part of the booking process.


Because every holiday we book is bespoke, availability changes from day to day and our booking process works as follows:


  • You provisionally book the tour you are interested in for your preferred dates and pay a 20% deposit online or by phone.
  • We confirm availability and book all your accommodation and options and send final confirmation as soon as everything is confirmed (max 5 working days).
  • If we are unable to accommodate you on your confirmed dates/tour or an alternative of your choice your deposit is fully refunded.

Available
  • Jan
  • Feb
  • Mar
  • Apr
  • May
  • Jun
  • Jul
  • Aug
  • Sep
  • Oct
  • Nov
  • Dec
Code Tour Name Duration Grade From Book
WItSFS Tuscany: From Florence to Siena 8 Days & 7 Nights £755 Book

Included:

  • 7 nights accommodation including breakfast
  • Luggage transfers as per your itinerary. 
  • Private transfer from Florence to Greve in Chianti, Greve in Chianti to Monte San Michele and Radda in Chianti to Siena
  • 24-hour telephone assistance
  • Detailed route notes and maps

Excluded:

  • All lunches & Dinners
  • Flights and public transportation
  • Travel insurance
  • Admissions and entrance fees of any kind.
  • Personal expenses such as lunch, dinner, snacks, wine tasting, drinks, phone calls, etc.
  • Any item that has not been specifically mentioned in the program

Optional Extras: 

  • Additional nights en route or elsewhere in Italy
  • Airport Transfers.
  • Guided tours of Florence or Siena with private local city guide.
  • Cooking lessons in Florence or Siena

Price from: £755 Book Now


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