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 in Radda in Chianti and the idyllic setting of Gaiole in Chianti. 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, the birthplace of the Renaissance
  • Walk through classic Tuscan landscapes of rolling hills, vineyards and olive groves
  • Option to sample the world-class Chianti wines of Volpaia and Brunello
  • Explore the wine towns of Greve, Radda, Gaiole and Lecchi in Chianti
  • Option to visit the Uffizi Gallery in Florence, where works of Da Vinci, Caravaggio and Botticelli hang
  • Marvel at the grandeur of Piazza del Campo in Siena

AT A GLANCE

TRIP LENGTH
7 DAYS
WALK GRADE
Moderate
PRICE FROM
$ 1075 per person twin/double share
SINGLE OCCUPANCY
$ 395 per person

ITINERARY

WHAT’S INCLUDED

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

ACCOMMODATION & DINING

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. Lunches are available at various cafes or food stores daily. There are numerous places to get dinner each night, your hosts will give you a list of recommendations. 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

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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 walking more 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 them for your own device.

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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 the 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 marks 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.

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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 Centrale 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 at 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).

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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.

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INSURANCE

We require that you have adequate travel insurance against potential losses, damage or injury, including cancellation costs and loss of luggage.

For all trips that require international travel, you must have purchased travel insurance that also includes medical evacuation coverage.

We also charge a cancellation fee if you cancel your walking holiday after we have confirmed it to cover costs incurred from our suppliers and in the office.  See the FAQ section for more information.

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CONTACT

If you have any questions, feel free to ask one of our destination consultants. You can get in touch with us via our contact form or email us at info@Stroll.com

MAP

DEPARTURE DATES

  • DATES
    AVAILABILITY
    PRICE
    Single Occupancy
    Details
  • 1 Apr 2023 - 31 Oct 2023
    AVAILABLE
    from

    $ 1075

    SINGLE OCCUPANCY
    $ 395

    Not available from 1st July – 22nd August

  • 1 Apr 2024 - 31 Oct 2024
    AVAILABLE
    from

    $ 1130

    SINGLE OCCUPANCY
    $ 395

    Not available from 1st July – 22nd August

AT A GLANCE
TRIP LENGTH
7 DAYS
WALK GRADE
oderate
PRICE FROM
$ 1075 per person twin/double share
SINGLE OCCUPANCY
$ 395 per person
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 in Radda in Chianti and the idyllic setting of Gaiole in Chianti. 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, the birthplace of the Renaissance
  • Walk through classic Tuscan landscapes of rolling hills, vineyards and olive groves
  • Option to sample the world-class Chianti wines of Volpaia and Brunello
  • Explore the wine towns of Greve, Radda, Gaiole and Lecchi in Chianti
  • Option to visit the Uffizi Gallery in Florence, where works of Da Vinci, Caravaggio and Botticelli hang
  • Marvel at the grandeur of Piazza del Campo in Siena
Itinerary
What’s Included
  • 7 nights ensuite room accommodation in Guesthouses, 3* & 4* Hotels
  • All luggage transfers taxi transfers as described in the itinerary
  • Option to upgrade to a wine resort in Gaiole in Chianti
  • 6 breakfasts
  • Maps, daily walk notes and information pack
  • Flexible itinerary to suit your walking needs
  • Enjoy worry-free navigation with your comprehensive maps, route notes and guidebook
Accommodation & Dining

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. Lunches are available at various cafes or food stores daily. There are numerous places to get dinner each night, your hosts will give you a list of recommendations. 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 walking more 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 them 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 the 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 marks 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 Centrale 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 at 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.

INSURANCE

We require that you have adequate travel insurance against potential losses, damage or injury, including cancellation costs and loss of luggage.

For all trips that require international travel, you must have purchased travel insurance that also includes medical evacuation coverage.

We also charge a cancellation fee if you cancel your walking holiday after we have confirmed it to cover costs incurred from our suppliers and in the office.  See the FAQ section for more information.

CONTACT

If you have any questions, feel free to ask one of our destination consultants. You can get in touch with us via our contact form or email us at info@Stroll.com

Map
Departure Dates
  • DATES
    AVAILABILITY
    PRICE
    Single Occupancy
    DETAILS
  • 1 Apr 2023 - 31 Oct 2023
    AVAILABLE
    from $ 1075
    SINGLE OCCUPANCY
    $ 395
  • 1 Apr 2024 - 31 Oct 2024
    AVAILABLE
    from $ 1130
    SINGLE OCCUPANCY
    $ 395
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: 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.

ENQUIRE NOW

If you’re looking for further information on any of our walking holidays please fill out the enquiry form and we’ll be in touch.
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