Florence to Siena Walk
Florence to Siena Walk
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Don't miss the magical landscapes of Tuscany from Florence, the birthplace of the Renaissance, to Siena, a medieval city and a UNESCO World Heritage Site. During this extraordinary walking holiday, you can discover the Chianti region among peaceful forests, vineyards, valleys, villages and farms.
An unforgettable trip through the wonderful city of Florence where you can see Michelangelo's David and the stunning Duomo. In addition, at the end of your walks you can try the world famous Chianti wines.
- Discover the wonderful cities of Florence and Siena.
- Walk through the Chianti region of Tuscany and explore among quiet forests and villages.
- Taste the world-class wines of the region.
- Walk paths amongst vineyards, olive groves and cypress trees.
- Walk through medieval Siena, a true open-air museum.
Gallery
Itinerary
Day 1 - Arrival in Florence
Florence is the birthplace of the Italian Renaissance, a city whose beauty is intertwined with history, art and culture as part of its everyday life. We recommend walking through its ancient streets to observe the Baroque and Gothic cathedrals, in addition to the fortresses. Don't miss Ponte Vecchio, Pitti Palace and Uffizi Degli Gallery.
After touring these iconic points of the city, we recommend you enjoy an evening stroll through Piazza Della Repubblica. This Italian social ritual is called "passeggiate" and consists of touring the place, observing the rest of the people and enjoying a tasty dinner in an "osteria" with gourmet cuisine.
You can reach Florence by tram, bus or train from Florence (15 minutes) or Pisa (1 hour) airports.
After touring these iconic points of the city, we recommend you enjoy an evening stroll through Piazza Della Repubblica. This Italian social ritual is called "passeggiate" and consists of touring the place, observing the rest of the people and enjoying a tasty dinner in an "osteria" with gourmet cuisine.
You can reach Florence by tram, bus or train from Florence (15 minutes) or Pisa (1 hour) airports.
Overnight in Florence
Classic Hotel
This family-friendly accommodation is located in a fully restored 19th-century guesthouse. It is just minutes away on foot from cafes, bars, and Florence's main points of interest.
*If there is no availability at this accommodation, you will stay in one of a similar category.
*If there is no availability at this accommodation, you will stay in one of a similar category.
Day 2 - Enjoy your day in Florence 4 miles | 6 km
During the morning we recommend a self-guided walk through the city exploring works of art and iconic places.
Discover Palazzo Vecchio, the Academy Gallery with Michelangelo's David and see the impressive Duomo of Florence Cathedral.
Enjoy the afternoon off by touring more corners in this stunning city and tasting the traditional gastronomy of the area.
Ascent: 208m (682ft) / Descent: 210m (689ft)
Discover Palazzo Vecchio, the Academy Gallery with Michelangelo's David and see the impressive Duomo of Florence Cathedral.
Enjoy the afternoon off by touring more corners in this stunning city and tasting the traditional gastronomy of the area.
Ascent: 208m (682ft) / Descent: 210m (689ft)
Overnight in Florence
Classic Hotel
This family-friendly accommodation is located in a fully restored 19th-century guesthouse. It is just minutes away on foot from cafes, bars, and Florence's main points of interest.
*If there is no availability at this accommodation, you will stay in one of a similar category.
*If there is no availability at this accommodation, you will stay in one of a similar category.
Day 3 - Florence to Radda in Chianti 8 miles | 13 km
After enjoying a rich breakfast, we will transfer you in 1.5 hours to the wonderful medieval town of Radda, in Chianti.
Walk uphill to Castelvecchi and see the Church of Pieve di Santa Maria Novella and the views of the vineyards at the top of the hill. Continue along a small wooded path and enjoy the panoramic views over the valley.
Continue to the lovely village of Volpaia, where you can pause and enjoy a delicious lunch. Finally, walk through the rows of cypress trees to Radda, where you can eat homemade pasta accompanied by a glass of the famous Chianti red wine.
Ascent: 448m (1,469ft) / Descent: 536m (1,758ft)
Walk uphill to Castelvecchi and see the Church of Pieve di Santa Maria Novella and the views of the vineyards at the top of the hill. Continue along a small wooded path and enjoy the panoramic views over the valley.
Continue to the lovely village of Volpaia, where you can pause and enjoy a delicious lunch. Finally, walk through the rows of cypress trees to Radda, where you can eat homemade pasta accompanied by a glass of the famous Chianti red wine.
Ascent: 448m (1,469ft) / Descent: 536m (1,758ft)
Overnight in Radda in Chianti
Palazzo San Niccolo
In the heart of the Chianti area, this comfortable 4-star hotel offers an unbeatable location with a perfect blend of tradition and modernity.
*If there is no availability at this accommodation, you will stay in one of a similar category.
*If there is no availability at this accommodation, you will stay in one of a similar category.
Day 4 - Radda in Chianti to Gaiole in Chianti 9 miles | 14 km
Today's walk will take you along paths through orchards, slopes, olive groves, wooded valleys and a large concentration of vineyards. You will arrive in Vertine, a medieval walled hamlet with a castle where you can admire the Church of St. Bartholomew, dating from the 11th century, as well as Renaissance works of the Florentine school.
In Vertine, you will also find a winery where it is possible to take part in a wine tasting before walking down to Gaiole.
Ascent: 439m (1,440ft) / Descent: 602m (1,975ft)
In Vertine, you will also find a winery where it is possible to take part in a wine tasting before walking down to Gaiole.
Ascent: 439m (1,440ft) / Descent: 602m (1,975ft)
Overnight in Gaiole in Chianti
Hotel Paradiso in Chianti
Cozy and family-friendly, Hotel Paradiso is the only one in the city center and is ideal for an unforgettable vacation discovering the charms of Chianti. All rooms are decorated in Tuscan style, with traditional terracotta floors and exposed beam ceilings, and feature a private bathroom.
*If there is no availability at this accommodation, you will stay in one of a similar category.
*If there is no availability at this accommodation, you will stay in one of a similar category.
Day 5 - Enjoy your day in Gaiole in Chianti 9 miles | 15 km
Through forests, olive groves and vineyards you can get to know the variety of landscapes offered by Chianti. 1.5 km from Gaiole, you will find the Riecine Winery, where you can have a wine tasting visit. It is open from Monday to Saturday and aims to create the best wines from Sangiovese, the grape from the Chianti Classico region.
It continues to the village of Montegrossi, and the impressive Monastery of Badia to Coltibuono that stands out for its tradition of expert viticulture dating back to the 12th century.
Ascent: 426m (1,398ft) / Descent: 426m (1,398ft)
It continues to the village of Montegrossi, and the impressive Monastery of Badia to Coltibuono that stands out for its tradition of expert viticulture dating back to the 12th century.
Ascent: 426m (1,398ft) / Descent: 426m (1,398ft)
Overnight in Gaiole in Chianti
Hotel Paradiso in Chianti
Cozy and family-friendly, Hotel Paradiso is the only one in the city center and is ideal for an unforgettable vacation discovering the charms of Chianti. All rooms are decorated in Tuscan style, with traditional terracotta floors and exposed beam ceilings, and feature a private bathroom.
*If there is no availability at this accommodation, you will stay in one of a similar category.
*If there is no availability at this accommodation, you will stay in one of a similar category.
Day 6 - Gail in Chianti to Lecchi 6 miles | 10 km
Among the more than 70,000 hectares of Chianti you can still find wild boars, hares, deer and pheasants, and you may be lucky enough to see one of these animals during the tour.
Afterwards, you can stop by Lecchi in Chianti, a beautiful stone village with medieval origins with narrow alleys and a charming atmosphere.
Ascent: 382m (1,253ft) / Descent: 315m (1,033ft)
Afterwards, you can stop by Lecchi in Chianti, a beautiful stone village with medieval origins with narrow alleys and a charming atmosphere.
Ascent: 382m (1,253ft) / Descent: 315m (1,033ft)
Overnight in Lecchi
Le Pozze di Lecchi
Hotel Le Pozze di Lecchi offers two outdoor pools with panoramic views of the Tuscan vineyards and hills. Each room here will provide you with a satellite TV, a mini-bar and air conditioning. It features an excellent restaurant with an outdoor terrace serving traditional local cuisine.
*If there is no availability at this accommodation, you will stay in one of a similar category.
*If there is no availability at this accommodation, you will stay in one of a similar category.
Day 7 - Lecchi to Siena 12 miles | 20 km
We will take you to the charming village of San Sano, so you can start your walk to Siena through beautiful and timeless landscapes. You will pass next to the Basilicata dell'Osservanza, from where you can enjoy fantastic views of this glorious medieval city.
Ascent: 574m (1,883ft) / Descent: 629m (2,063ft)
Ascent: 574m (1,883ft) / Descent: 629m (2,063ft)
Overnight in Siena
La Chicca B&B
This family-friendly property offers spacious rooms with fans and central heating. It is set in an old villa in San Prospero on the outskirts of Siena's historic walls, just a 5-minute walk from Piazza Campo.
*If there is no availability at this accommodation, you will stay in one of a similar category.
*If there is no availability at this accommodation, you will stay in one of a similar category.
Day 8 - Siena
From Siena you can go by train to Florence (1h 30m), Pisa (1h 45 m) or Rome (3h30m) from where you can take a flight to return home or continue your journey.
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End of our services.
Itinerary Map
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Services
Included
- Accommodation in en suite rooms in charming hotels
- Daily Breakfasts
- Luggage transfers between accommodations
- Information dossier with maps and routes
- 24-hour telephone support
- Sustainable travel, we compensate the CO2 emissions of your trip
- Taxes
Extras
- Travel insurance
- Cancellation insurance
- Additional nights
Accomodation
General information
The accommodations with which we collaborate have a private bathroom and all the necessary services to ensure the best comfort available.
Our team checks in situ the quality of all the accommodations offered, so that you have an unforgettable experience during your trip.
The accommodation that we will book for your trip will be selected taking into account our commitment to you: guaranteeing comfort, calm and enjoyment throughout your trip.
We work with quality hotels and country cottages with limited capacity, so we invite you to confirm your reservation as soon as possible.
The name of each accommodation will be provided to you a few weeks before your trip begins.
Room types
It is possible to book this journey in single, double or triple rooms.
All rooms have private bathrooms.
Travel & Transfers
To get to Florence you can take a flight to Pisa, Rome or directly to Florence, although there are fewer flights available. From Florence Airport it takes only 15 minutes to reach the city centre by train or bus.
If you come from Pisa Airport, you can take a transfer to Pisa Centrale station and there, take a train that takes 1h 15m to Florence.
From Rome Airport you can take a Leonardo Express train to the city centre and then a train to Florence that takes approximately 2 hours.
When you finish your trip in Siena you can take a train to Florence or Pisa Centrale station and then take another transfer to the airport.
You can also go to Rome, only it is a little more complicated, as you must take a train to Florence and then another train to Rome. Trains depart very often and the journey takes 3 h 30 min, depending on the number of stops. Once you arrive in the centre of Rome you can take the Leonardo Express train to Rome Fiumicino Airport.
On the TrenItalia website, you can check the current timetables.
If you come from Pisa Airport, you can take a transfer to Pisa Centrale station and there, take a train that takes 1h 15m to Florence.
From Rome Airport you can take a Leonardo Express train to the city centre and then a train to Florence that takes approximately 2 hours.
When you finish your trip in Siena you can take a train to Florence or Pisa Centrale station and then take another transfer to the airport.
You can also go to Rome, only it is a little more complicated, as you must take a train to Florence and then another train to Rome. Trains depart very often and the journey takes 3 h 30 min, depending on the number of stops. Once you arrive in the centre of Rome you can take the Leonardo Express train to Rome Fiumicino Airport.
On the TrenItalia website, you can check the current timetables.
FAQs
Is luggage transfer included? What are the luggage requirements?
Absolutely! Each traveller has included 1 piece of luggage that we will transfer between your accommodations. It's important that this piece of luggage meets the following criterias:
- Maximum weight of 45 lbs (20 kg).
- Must be only 1 piece of luggage without any attachments or accessories.
- Should not contain valuables, fragile items, food or medications.
- Must be correctly identified (booking reference of your trip and the full name of the trip holder).
What should my physical preparation be?
This route is classified as moderate because the terrain has rugged areas. It is recommended to be in good shape to enjoy it fully.
How far in advance should I book my trip?
It is an extremely popular region so we suggest you book as soon as you are sure of your dates. Between July 2nd and August 16th, the Palio de Siena Festival is held in the city, making availability very difficult.
What walking equipment should I bring on my holiday?
We recommend wearing comfortable clothing, including hats and gloves. In addition to a backpack for daily tours and shoes or walking boots, ideally waterproof.
In our information dossier, you will find a detailed list of everything you should carry.
What is the best time of year to travel?
If you prefer to do this trip in a slightly cooler climate, we recommend the months of May, June, September and October, where you can enjoy the vibrant colours of Tuscany.
July and August can be very hot, so if you decide to go on these dates, it is best to start walking early.
What is the best airport to get there?
The airports of Florence, Pisa and Rome are the most convenient to fly both nationally and internationally. Most destinations have a central train station for arrival and departure.
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