OVERVIEW

Discover the fine wines and rustic dishes of Tuscany’s Chianti region as you explore the trails and medieval walled towns between Florence and Siena. Starting out at Europe’s most celebrated city of art, Florence, stroll across the Ponte Vecchio bridge and visit the Uffizi gallery where the Renaissance masterpieces of Carravagio, Botticelli and Da Vinci hang.

Journey south into a perfectly formed landscape of rolling hills, cloaked in olive groves and neatly terraced vineyards. Follow forested trails and farmers tracks into a succession of historic hilltop towns, founded by the Etruscans over 2000 years ago. Meander through the piazza of Radda in Chianti where you can dine on bowls of fresh pappardelle pasta or wild boar stew. Walk to the idyllic setting of Gaiole in Chianti and sample wines and local olive oils. The finale of this tour, takes you into the majesty of Siena’s Piazza del Campo, the perfect opportunity to round off the walk with a local Chianti.

 

HIGHLIGHTS:

  • Journey from Florence to Siena and discover Tuscany’s Chianti Winelands
  • Explore the UNESCO city of Florence, birthplace of the Renaissance
  • Visit the Uffizi Gallery, where works of Da Vinci, Caravaggio and Botticelli hang
  • Walk through classic Tuscan landscapes of rolling hills, vineyards and olive groves
  • Sample the world class Chianti wines of Volpaia and Brunello
  • Explore the wine towns of Greve, Radda, Gaiole and Lecchi in Chianti
  • Dine on bowls of fresh pappa al pomodoro
  • Marvel at the grandeur of Piazza del Campo in Siena

WALK OVERVIEW

TYPE OF WALK
SELF GUIDED
TRIP LENGTH
7 DAYS
WALK GRADE
Moderate

Grade 3 – Moderate

Short, steep hill sections. Moderate active lifestyle and some walking experience recommended.

PRICE FROM
$ 2195

per person twin/double share

SINGLE OCCUPANCY
$ 955

Accommodations charge the same price per room regardless of whether there are one or two people occupying it. To cover the cost of the accommodation when occupied by one person we need to charge the single occupancy fee.

per person

Book now

ITINERARY

  • Day 1
  • Day 2
  • Day 3
  • Day 4
  • Day 5
  • Day 6
  • Day 7

DAY 1
Arrive Florence

Cradle of the Renaissance, Florence is a city of fine art, fashion and exceptional architecture. Many of Florence’s sights need little introduction. Stroll across the medieval Ponte Vecchio bridge and head to the world-famous Uffizi art gallery where the masterpieces of Leonardo da Vinci and Raphael hang. Visit the Galleria dell’Accademia to see Michelangelo’s statue of David and walk through cobbled streets to Piazza del Duomo to marvel at the exquisite designs of Brunelleschi.

Meals included: None
Accommodation: Hotel David
Located on the southern side of the River Arno, the hotel is set in a 19th century building only a couple minutes’ walk from the Arno River. Classically furnished rooms have a free mini-bar and breakfast is well known for its selection of homemade pastries. The historic centre is a 5-minute bus journey, or you can enjoy a 20 minute riverside walk to Ponte Vecchio and cross into the splendour of Florence.

DAY 2
Transfer to Greve in Chianti, Loop Walk

Begin with a private transfer to the wine town of Greve in Chianti where its charming piazza is the starting point for todays walk. Leaving the town on foot, climb to the hilltop hamlet of Montefioralle. Once a significant stronghold during the 13th century Sienese-Florentine conflict, take time to explore the cavern of streets or enjoy lunch in one of the rustic restaurants. Return to Greve along a typical white gravel road, known locally as ‘Strade Bianche’. Tonight you will dine at your family run hotel.

Walk: 9km
Ascent: 350m
Descent: 350m
Meals included: Breakfast & Dinner
Accommodation: Albergo Chianti
Owned by the Buys family of the Le Maurcy wine cellar, this 3* hotel is located just off the main piazza. Simple, comfortable en-suite rooms provide a good night’s sleep and the hotel restaurant is a favourite with locals and tourists alike. If you arrive in good time you can take a dip in the hotel pool or take advantage of the bar and terrace area.

DAY 3
Walk to Radda in Chianti

After a short taxi transfer deep into the Chianti winelands begin your walk on a forested trail to the fortified village of Volpaia, home of the revered Volpaia red wine (a must to sample while you are here). Steeped in wine making tradition, the town has been producing wine since the late 12th century. Beyond Volpaia, the trail follows typical ‘white roads’ lined with cypress trees as you ascend to the hilltop church of Santa Maria Novella (which has retained its original Romanesque structure). The trail rolls on through vineyards to the hilltop town of Radda in Chianti, one of the most celebrated wine towns of the Chianti region.

Walk: 13.5km
Ascent: 500m
Descent: 660m
Meals included: Breakfast & Walkers Lunch
Accommodation: Hotel Palazzo San Niccolo
An elegant 4* hotel in Radda’s the Ciacci and Palagi. Within the building is a peaceful courtyard where you can relax with a glass of local Chianti or head into the garden to soak up the Tuscan sun. Rooms have been classically designed, in keeping with the history of the building. Before you leave this hotel, do take time to visit the small sitting room with an incredibly well-preserved fresco that is said to be a symbol of unity between the 2 families.

DAY 4
Walk to Gaiole in Chianti

A gentle start begins with a descent southwards to your destination today, Gaiole in Chianti. Walk through wooded valleys, vineyards and olive groves. Enjoy rambling through picture postcard Tuscan landscapes, passing through the hamlets of San Guisto in Salcio and Adine. Descend into the sleepy streets of Gaiole in Chianti where you will spend the next two nights and have the opportunity to learn more of the Chianti wine production and signature Tuscan dishes of Gaiole in Chainti.

Walk: 12km
Ascent: 350m
Descent: 500m
Meals included: Breakfast & Walkers Lunch
Accommodation: Cavarichino
A restored farmhouse on the outskirts of Gaiole, Cavarchino is a charming family run bed and breakfast. On arrival, you can relax in the gardens or take a dip in the pool before strolling into Gaiole centre for dinner. Your host, Irene is always happy to help out with any questions or assistance you might need whilst in Gaiole.

DAY 5
Loop Walk in Gaiole in Chianti

Walk through the medieval streets of Gaiole and into the rich Tuscan countryside as the route climbs to Castello di San Donato in Perano, a cluster of well-preserved 10th century houses. Continue on through woodland trails which will see you arrive at the hamlet of Badia a Coltibuono. For over 1000 years the Coltibuono farm has been producing wines, olive oils and s a great spot for lunch before walking to the hilltop village of Montegrossi. A gentle but straightforward ramble descends back to the tranquility of Gaiole and your hotel.

Walk: 19.5km ot 15km
Ascent: 660m or 400m
Descent: 600m or 250m
Meals included: Breakfast
Accommodation: Cavarichino

DAY 6
Walk to Lecchi in Chianti, transfer to Siena

Follow trails across a rolling landscape of olive groves and vineyards of Castelle di Meteo where since 1256 much of the land has been dedicated to producing this prestigious wine. Onwards from Castelle, much of the land is cloaked in oak woods and you might be lucky enough to spot an elusive deer en-route. Arriving into Lecchi Chainti, little has changed in this delightful town since the 12th century. From Lecchi, a private transfer will take you onwards to Siena and a visit to Piazza del Campo, one of the largest medieval squares in the world.

Walk: 11km
Ascent: 350m
Descent: 300m
Meals included: Breakfast
Accommodation: Hotel Chiusarelli
Round off your week with a night in a typical neoclassical villa dating back to the 1870’s. Located in the historical centre, several years ago the hotel was refurbished to a traditional Sienese house, complete with a large, beautiful preserved frescos. A charming and fitting end to your walking trip.

DAY 7
Onward Travel

Depending on your onward travel arrangements, we’d suggest an early morning stroll around the streets of Siena and Piazza del Campo before the buzz of the crowds descend into the streets.

Meals included: Breakfast

WHAT’S INCLUDED

  • 7 nights ensuite room accommodation in Guesthouses, 3* & 4* Hotels
  • All luggage transfers
  • All taxi transfers as described in the itinerary
  • Option to upgrade to a wine resort in Gaiole in Chianti
  • 6 breakfasts 2 lunches and 1 dinner
  • Maps, daily walk notes and information pack
  • 24/7 telephone support
  • Flexible itinerary to suit your walking needs
  • Enjoy worry free navigation with your comprehensive maps, route notes and guidebook

ACCOMMODATION & DINING

OVERVIEW

During this tour you will spend each night in small family run boutique B&B’s and 3* and 4* hotels. Chosen for their location, facilities and history, each accommodation is used to welcoming walkers. Many of them will be family run so are very knowledgeable about the Chianti region and they will always be happy to chat with you about the history, food and wine. Of course, you can always call us too should you need anything during your walk. As many of the overnight stays are in small villages or towns, on occasion we may have to book another similar accommodation of equal standard. We will discuss these options with you during the booking process.

You will be provided with 6 breakfasts and 2 lunches and 1 dinner. If you have any food allergies or intolerances, please let us know at the time of booking so we can let your hosts know. Should you have severe food allergies, it’s always worth bringing a few of your own snacks with you.

GENERAL INFO

About the walking

We grade this walk as moderate. Tracks and trails may have short steep hill sections and rough surfaces. A moderate active lifestyle makes the walking enjoyable, an exercise regime of 2 to 3 times a week is needed.

Walks are generally along well defined trails. You should be used to walking between 10km-19km per day with up to 500m of ascent and descent. The vast majority of trails and tracks are well defined and cover a variety of terrain. On any typical day you will be walking on forest trails, gravel tracks, rolling farmland, through vineyards and into the villages and towns where you will stay. It is commonplace in Italy that there are no separate footpaths (even in the towns) which means you will often be walking on the roads. Please always be mindful of all road users when doing so. For each of the walks, you will be provided with daily walk notes, a map and the GPX tracks if you require to use for your own device.

Availability

This walk is available from late April to the end of June and mid-August through to October.

Not available from 1st July – 22nd August.

From April into May days are warm and sunny with equally pleasant evenings. Into June, sunflowers are in full bloom, vineyards are flowering, and the days become much warmer (up to 30 degrees). Village piazza’s buzz with life and are perfect for enjoying an al fresco dinner. Mid-August into September mark the beginnings of the grape harvests, so you might be lucky enough to encounter a local festival or two. By October, the summer heat has retreated. The days are warm with evenings cooling off. It isn’t uncommon for Tuscany to experience thunderstorms during summer days, so you should always be prepared for a change of season during the day.

How to get there and away

This walk starts in Florence and ends in Siena. Florence has a small airport, whereas the larger airports of Pisa and Rome generally offer a wider range of routes across Europe and beyond.

Florence airport
You can travel by either bus or tram from Florence airport to Florence centre. The direct tram services terminate next to the Florence mainline station, whereas the bus service terminates in central Florence. Both journeys are no longer than 20mins.

Pisa Airport
From Pisa Airport you can take the ‘Pisa Mover’ train shuttle to the Pisa Central station to change for direct services to Florence. Journey time is between 1hr-1hr 30mins

Rome Airport
Rome has two airports. Fiumicino and Ciampino. Fiumicino airport connects through to Florence Central station in around 2hrs 30mins (with a change of trains in Rome central station). If you’re arriving into Rome Ciampino airport you will need to take the airport bus to Ciampino station and change at Rome central station for services for Florence. Journey time from Ciampino to Florence is around 2hrs 30mins (depending on times and services).

Onward Travel From Siena

Siena does not have an airport but does have excellent train connections to Florence (direct service, 1hr 30mins), Pisa (change at Empoli, 1hr 45mins) and Rome (via Chiusi Chianciano Terme, 4hrs or via Florence, 3hrs 15mins).

For all train travel in Italy prices, timetables and ticket reservations can be made through The Trainline or Tren Italia.

Another useful generic planning tool for travel is Rome2Rio should you be travelling from, or to, other destinations.

MAP

DEPARTURE DATES

  • DATES
    AVAILABILITY
    PRICE
    Single Occupancy
    DETAILS
  • 1 Apr 2020 - 31 Oct 2020
    AVAILABLE
    from

    $2195

    SINGLE OCCUPANCY
    $955

    Not available from 1st July – 22nd August

  • 1 Apr 2021 - 31 Oct 2021
    AVAILABLE
    from

    $2295

    SINGLE OCCUPANCY
    $955

    Not available from 1st July – 22nd August

FAQS

Q: What happens if I don’t want to walk one of the days?

As some of the walks on this itinerary are loop walks you can relax in the grounds of your accommodation (some of which have a pool) or explore the local town and its wineries. On the days where you will be walking to the next town, it might be possible to travel with the taxi service which transports your luggage. You can also use the local bus service between towns. Your accommodation hosts will have up to date information and advice should you wish to travel to the next destination by local transport. There is always plenty of information about options for the day in your daily walk notes and as always, you can call us at the office for any help during your walk should you need any assistance.

Q: Where would you suggest adding an extra night?

Florence. With so much world-famous Renaissance art and delicious food to sample, Florence is worthy of an extra day. From Florence you can also hop on the train to nearby Pisa (1-hour journey) to see the world-famous leaning tower. Radda in Chianti and / or Gaiole in Chianti Historic towns which are best experienced by relaxing poolside at your hotel and sampling the locally produced Chianti. In the evening enjoy typical dishes such as pappa al pomodoro, beef ragu pasta and wild boar stew. Siena. An incredibly well-preserved city with the show stopping Piazza del Campo at the heart of Sienese life. It is also possible to take a short bus journey to the hilltop towers of San Gimignano (an hour journey, or private transfers can be quoted and arranged).

Q: Can you extend our stay in Siena?

Of course, please let us know at the time of booking if you would like to extend your time in Siena. There is so much to see, we’d suggest at least 1 extra night.

Q: Can my children walk with me?

We don't allow children under 16 to go on this walk. We're also unable to offer discounted rates for children.

Q: Is this tour OK for solo walkers?

Yes this tour is suitable for solo walkers. It is likely you’ll bump into other walkers along the trails and in many of the places you will stay. You will also pass through villages and towns should you need any assistance. Generally there is always good network coverage for mobile phones, should you worry about walking alone.

Q: We’re travelling as friends, can we get a triple room?

Triple rooms are in limited availability. Some accommodations do not offer triple rooms but we can always provide a twin or double room with a single room.

Q: Can we reduce the days walked?

Easily! This tour has been created with flexibility in mind. You can easily remove the loop walk in Gaiole in Chianti on day 5 and if you already have plans to be in Florence, we can collect you in Florence and take you directly to Greve in Chianti on day 1. We’re always happy to discuss your needs.

Q: Can we extend the days walked?

Of course, you may want to start by looking at our Tuscan Explorer which is 10 days and 9 nights, starting in Florence and ending in southern wine town of Montepulciano.

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Overview

OVERVIEW

Discover the fine wines and rustic dishes of Tuscany’s Chianti region as you explore the trails and medieval walled towns between Florence and Siena. Starting out at Europe’s most celebrated city of art, Florence, stroll across the Ponte Vecchio bridge and visit the Uffizi gallery where the Renaissance masterpieces of Carravagio, Botticelli and Da Vinci hang.

Journey south into a perfectly formed landscape of rolling hills, cloaked in olive groves and neatly terraced vineyards. Follow forested trails and farmers tracks into a succession of historic hilltop towns, founded by the Etruscans over 2000 years ago. Meander through the piazza of Radda in Chianti where you can dine on bowls of fresh pappardelle pasta or wild boar stew. Walk to the idyllic setting of Gaiole in Chianti and sample wines and local olive oils. The finale of this tour, takes you into the majesty of Siena’s Piazza del Campo, the perfect opportunity to round off the walk with a local Chianti.

 

HIGHLIGHTS:

  • Journey from Florence to Siena and discover Tuscany’s Chianti Winelands
  • Explore the UNESCO city of Florence, birthplace of the Renaissance
  • Visit the Uffizi Gallery, where works of Da Vinci, Caravaggio and Botticelli hang
  • Walk through classic Tuscan landscapes of rolling hills, vineyards and olive groves
  • Sample the world class Chianti wines of Volpaia and Brunello
  • Explore the wine towns of Greve, Radda, Gaiole and Lecchi in Chianti
  • Dine on bowls of fresh pappa al pomodoro
  • Marvel at the grandeur of Piazza del Campo in Siena

WALK OVERVIEW

TYPE OF WALK
SELF GUIDED
TRIP LENGTH
7 DAYS
WALK GRADE
Moderate

Grade 3 – Moderate

Short, steep hill sections. Moderate active lifestyle and some walking experience recommended.

PRICE FROM
$ 2195

per person twin/double share

SINGLE OCCUPANCY
$ 955

Accommodations charge the same price per room regardless of whether there are one or two people occupying it. To cover the cost of the accommodation when occupied by one person we need to charge the single occupancy fee.

per person

Book now
Itinerary

ITINERARY

  • Day 1
  • Day 2
  • Day 3
  • Day 4
  • Day 5
  • Day 6
  • Day 7

DAY 1
Arrive Florence

Cradle of the Renaissance, Florence is a city of fine art, fashion and exceptional architecture. Many of Florence’s sights need little introduction. Stroll across the medieval Ponte Vecchio bridge and head to the world-famous Uffizi art gallery where the masterpieces of Leonardo da Vinci and Raphael hang. Visit the Galleria dell’Accademia to see Michelangelo’s statue of David and walk through cobbled streets to Piazza del Duomo to marvel at the exquisite designs of Brunelleschi.

Meals included: None
Accommodation: Hotel David
Located on the southern side of the River Arno, the hotel is set in a 19th century building only a couple minutes’ walk from the Arno River. Classically furnished rooms have a free mini-bar and breakfast is well known for its selection of homemade pastries. The historic centre is a 5-minute bus journey, or you can enjoy a 20 minute riverside walk to Ponte Vecchio and cross into the splendour of Florence.

DAY 2
Transfer to Greve in Chianti, Loop Walk

Begin with a private transfer to the wine town of Greve in Chianti where its charming piazza is the starting point for todays walk. Leaving the town on foot, climb to the hilltop hamlet of Montefioralle. Once a significant stronghold during the 13th century Sienese-Florentine conflict, take time to explore the cavern of streets or enjoy lunch in one of the rustic restaurants. Return to Greve along a typical white gravel road, known locally as ‘Strade Bianche’. Tonight you will dine at your family run hotel.

Walk: 9km
Ascent: 350m
Descent: 350m
Meals included: Breakfast & Dinner
Accommodation: Albergo Chianti
Owned by the Buys family of the Le Maurcy wine cellar, this 3* hotel is located just off the main piazza. Simple, comfortable en-suite rooms provide a good night’s sleep and the hotel restaurant is a favourite with locals and tourists alike. If you arrive in good time you can take a dip in the hotel pool or take advantage of the bar and terrace area.

DAY 3
Walk to Radda in Chianti

After a short taxi transfer deep into the Chianti winelands begin your walk on a forested trail to the fortified village of Volpaia, home of the revered Volpaia red wine (a must to sample while you are here). Steeped in wine making tradition, the town has been producing wine since the late 12th century. Beyond Volpaia, the trail follows typical ‘white roads’ lined with cypress trees as you ascend to the hilltop church of Santa Maria Novella (which has retained its original Romanesque structure). The trail rolls on through vineyards to the hilltop town of Radda in Chianti, one of the most celebrated wine towns of the Chianti region.

Walk: 13.5km
Ascent: 500m
Descent: 660m
Meals included: Breakfast & Walkers Lunch
Accommodation: Hotel Palazzo San Niccolo
An elegant 4* hotel in Radda’s the Ciacci and Palagi. Within the building is a peaceful courtyard where you can relax with a glass of local Chianti or head into the garden to soak up the Tuscan sun. Rooms have been classically designed, in keeping with the history of the building. Before you leave this hotel, do take time to visit the small sitting room with an incredibly well-preserved fresco that is said to be a symbol of unity between the 2 families.

DAY 4
Walk to Gaiole in Chianti

A gentle start begins with a descent southwards to your destination today, Gaiole in Chianti. Walk through wooded valleys, vineyards and olive groves. Enjoy rambling through picture postcard Tuscan landscapes, passing through the hamlets of San Guisto in Salcio and Adine. Descend into the sleepy streets of Gaiole in Chianti where you will spend the next two nights and have the opportunity to learn more of the Chianti wine production and signature Tuscan dishes of Gaiole in Chainti.

Walk: 12km
Ascent: 350m
Descent: 500m
Meals included: Breakfast & Walkers Lunch
Accommodation: Cavarichino
A restored farmhouse on the outskirts of Gaiole, Cavarchino is a charming family run bed and breakfast. On arrival, you can relax in the gardens or take a dip in the pool before strolling into Gaiole centre for dinner. Your host, Irene is always happy to help out with any questions or assistance you might need whilst in Gaiole.

DAY 5
Loop Walk in Gaiole in Chianti

Walk through the medieval streets of Gaiole and into the rich Tuscan countryside as the route climbs to Castello di San Donato in Perano, a cluster of well-preserved 10th century houses. Continue on through woodland trails which will see you arrive at the hamlet of Badia a Coltibuono. For over 1000 years the Coltibuono farm has been producing wines, olive oils and s a great spot for lunch before walking to the hilltop village of Montegrossi. A gentle but straightforward ramble descends back to the tranquility of Gaiole and your hotel.

Walk: 19.5km ot 15km
Ascent: 660m or 400m
Descent: 600m or 250m
Meals included: Breakfast
Accommodation: Cavarichino

DAY 6
Walk to Lecchi in Chianti, transfer to Siena

Follow trails across a rolling landscape of olive groves and vineyards of Castelle di Meteo where since 1256 much of the land has been dedicated to producing this prestigious wine. Onwards from Castelle, much of the land is cloaked in oak woods and you might be lucky enough to spot an elusive deer en-route. Arriving into Lecchi Chainti, little has changed in this delightful town since the 12th century. From Lecchi, a private transfer will take you onwards to Siena and a visit to Piazza del Campo, one of the largest medieval squares in the world.

Walk: 11km
Ascent: 350m
Descent: 300m
Meals included: Breakfast
Accommodation: Hotel Chiusarelli
Round off your week with a night in a typical neoclassical villa dating back to the 1870’s. Located in the historical centre, several years ago the hotel was refurbished to a traditional Sienese house, complete with a large, beautiful preserved frescos. A charming and fitting end to your walking trip.

DAY 7
Onward Travel

Depending on your onward travel arrangements, we’d suggest an early morning stroll around the streets of Siena and Piazza del Campo before the buzz of the crowds descend into the streets.

Meals included: Breakfast

What’s Included

WHAT’S INCLUDED

  • 7 nights ensuite room accommodation in Guesthouses, 3* & 4* Hotels
  • All luggage transfers
  • All taxi transfers as described in the itinerary
  • Option to upgrade to a wine resort in Gaiole in Chianti
  • 6 breakfasts 2 lunches and 1 dinner
  • Maps, daily walk notes and information pack
  • 24/7 telephone support
  • Flexible itinerary to suit your walking needs
  • Enjoy worry free navigation with your comprehensive maps, route notes and guidebook
Accommodation & Dining

ACCOMMODATION & DINING

OVERVIEW

During this tour you will spend each night in small family run boutique B&B’s and 3* and 4* hotels. Chosen for their location, facilities and history, each accommodation is used to welcoming walkers. Many of them will be family run so are very knowledgeable about the Chianti region and they will always be happy to chat with you about the history, food and wine. Of course, you can always call us too should you need anything during your walk. As many of the overnight stays are in small villages or towns, on occasion we may have to book another similar accommodation of equal standard. We will discuss these options with you during the booking process.

You will be provided with 6 breakfasts and 2 lunches and 1 dinner. If you have any food allergies or intolerances, please let us know at the time of booking so we can let your hosts know. Should you have severe food allergies, it’s always worth bringing a few of your own snacks with you.

General Info

GENERAL INFO

About the walking

We grade this walk as moderate. Tracks and trails may have short steep hill sections and rough surfaces. A moderate active lifestyle makes the walking enjoyable, an exercise regime of 2 to 3 times a week is needed.

Walks are generally along well defined trails. You should be used to walking between 10km-19km per day with up to 500m of ascent and descent. The vast majority of trails and tracks are well defined and cover a variety of terrain. On any typical day you will be walking on forest trails, gravel tracks, rolling farmland, through vineyards and into the villages and towns where you will stay. It is commonplace in Italy that there are no separate footpaths (even in the towns) which means you will often be walking on the roads. Please always be mindful of all road users when doing so. For each of the walks, you will be provided with daily walk notes, a map and the GPX tracks if you require to use for your own device.

Availability

This walk is available from late April to the end of June and mid-August through to October.

Not available from 1st July – 22nd August.

From April into May days are warm and sunny with equally pleasant evenings. Into June, sunflowers are in full bloom, vineyards are flowering, and the days become much warmer (up to 30 degrees). Village piazza’s buzz with life and are perfect for enjoying an al fresco dinner. Mid-August into September mark the beginnings of the grape harvests, so you might be lucky enough to encounter a local festival or two. By October, the summer heat has retreated. The days are warm with evenings cooling off. It isn’t uncommon for Tuscany to experience thunderstorms during summer days, so you should always be prepared for a change of season during the day.

How to get there and away

This walk starts in Florence and ends in Siena. Florence has a small airport, whereas the larger airports of Pisa and Rome generally offer a wider range of routes across Europe and beyond.

Florence airport
You can travel by either bus or tram from Florence airport to Florence centre. The direct tram services terminate next to the Florence mainline station, whereas the bus service terminates in central Florence. Both journeys are no longer than 20mins.

Pisa Airport
From Pisa Airport you can take the ‘Pisa Mover’ train shuttle to the Pisa Central station to change for direct services to Florence. Journey time is between 1hr-1hr 30mins

Rome Airport
Rome has two airports. Fiumicino and Ciampino. Fiumicino airport connects through to Florence Central station in around 2hrs 30mins (with a change of trains in Rome central station). If you’re arriving into Rome Ciampino airport you will need to take the airport bus to Ciampino station and change at Rome central station for services for Florence. Journey time from Ciampino to Florence is around 2hrs 30mins (depending on times and services).

Onward Travel From Siena

Siena does not have an airport but does have excellent train connections to Florence (direct service, 1hr 30mins), Pisa (change at Empoli, 1hr 45mins) and Rome (via Chiusi Chianciano Terme, 4hrs or via Florence, 3hrs 15mins).

For all train travel in Italy prices, timetables and ticket reservations can be made through The Trainline or Tren Italia.

Another useful generic planning tool for travel is Rome2Rio should you be travelling from, or to, other destinations.

Map

MAP

Departure Dates

DEPARTURE DATES

  • DATES
    AVAILABILITY
    PRICE
    Single Occupancy
    DETAILS
  • 1 Apr 2020 - 31 Oct 2020
    AVAILABLE
    Details
    from

    $2195

    SINGLE OCCUPANCY
    $955
  • 1 Apr 2021 - 31 Oct 2021
    AVAILABLE
    Details
    from

    $2295

    SINGLE OCCUPANCY
    $955
Faqs

FAQS

Q: What happens if I don’t want to walk one of the days?

As some of the walks on this itinerary are loop walks you can relax in the grounds of your accommodation (some of which have a pool) or explore the local town and its wineries. On the days where you will be walking to the next town, it might be possible to travel with the taxi service which transports your luggage. You can also use the local bus service between towns. Your accommodation hosts will have up to date information and advice should you wish to travel to the next destination by local transport. There is always plenty of information about options for the day in your daily walk notes and as always, you can call us at the office for any help during your walk should you need any assistance.

Q: Where would you suggest adding an extra night?

Florence. With so much world-famous Renaissance art and delicious food to sample, Florence is worthy of an extra day. From Florence you can also hop on the train to nearby Pisa (1-hour journey) to see the world-famous leaning tower. Radda in Chianti and / or Gaiole in Chianti Historic towns which are best experienced by relaxing poolside at your hotel and sampling the locally produced Chianti. In the evening enjoy typical dishes such as pappa al pomodoro, beef ragu pasta and wild boar stew. Siena. An incredibly well-preserved city with the show stopping Piazza del Campo at the heart of Sienese life. It is also possible to take a short bus journey to the hilltop towers of San Gimignano (an hour journey, or private transfers can be quoted and arranged).

Q: Can you extend our stay in Siena?

Of course, please let us know at the time of booking if you would like to extend your time in Siena. There is so much to see, we’d suggest at least 1 extra night.

Q: Can my children walk with me?

We don't allow children under 16 to go on this walk. We're also unable to offer discounted rates for children.

Q: Is this tour OK for solo walkers?

Yes this tour is suitable for solo walkers. It is likely you’ll bump into other walkers along the trails and in many of the places you will stay. You will also pass through villages and towns should you need any assistance. Generally there is always good network coverage for mobile phones, should you worry about walking alone.

Q: We’re travelling as friends, can we get a triple room?

Triple rooms are in limited availability. Some accommodations do not offer triple rooms but we can always provide a twin or double room with a single room.

Q: Can we reduce the days walked?

Easily! This tour has been created with flexibility in mind. You can easily remove the loop walk in Gaiole in Chianti on day 5 and if you already have plans to be in Florence, we can collect you in Florence and take you directly to Greve in Chianti on day 1. We’re always happy to discuss your needs.

Q: Can we extend the days walked?

Of course, you may want to start by looking at our Tuscan Explorer which is 10 days and 9 nights, starting in Florence and ending in southern wine town of Montepulciano.

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