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A hiker rests on a low wall in front of the church of San Leolino, with a view down the valley to the vineyards

Picturesque Tuscany

Florence, medieval villages, wine & Tuscan cuisine

Bestseller
8 Days / 7 Nights
Moderate Walking
145  kg
CO₂-Emissions are offset
145  kg
CO₂-Emissions are offset
145  kg
CO₂-Emissions are offset
A hiker rests on a low wall in front of the church of San Leolino, with a view down the valley to the vineyards

The essentials at a glance

Explore Tuscany's iconic landscapes on this self-guided walking tour from Florence to the Tyrrhenian coast. Discover UNESCO-listed Siena, the medieval towers of San Gimignano, and the Etruscan village of Panzano. Walk through vineyards, olive groves, and pine forests with daily distances of 10-16 km. The route includes wine tasting, transfers between select locations, and accommodation in 3-4 star hotels and agriturismi. Moderate difficulty with up to 4.5 hours walking per day.

Do you have questions about this tour?

Culture, enjoyment and unique landscapes: all this and much more awaits you on our long-distance hiking trip in Tuscany. Florence, the beating heart of central Italy, welcomes you spectacularly. Magnificent palaces and cathedrals, Michelangelo’s David or the paintings by great masters such as Leonardo da Vinci and Botticelli. On lonely paths you travel through the typical hilly Tuscan landscape of the Chianti region, through historical places such as Siena and Volterra as you continue towards the Tuscan coast. On the Via Sale you can taste the salty sea air on your tongue and when you finally dip your tired hiking legs into the turquoise glittering waves of the Tyrrhenian Sea at Cecina Mare, you can be sure you have reached your destination!

  • All information and further tour tips for your hiking holiday in Tuscany.
In the little streets of Castellina in Chianti
The fountain square in San Gimignano at the evening hour
Hiking in Tuscany overlooking San Gimignano
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€999
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Sophia Altenberger
Sophia Altenberger
+43 6219 60877 184
Contact form
Book an appointment

Our eight-day hiking tour in Tuscany takes you in six daily stages from inland to the Tyrrhenian Sea. The starting point of your hiking holiday and the beginning of countless active experiences is Florence, the capital of Tuscany. Here it is not difficult to immediately immerse yourself in the Italian flair and the Mediterranean lifestyle. The journey takes you through the unmistakable landscape first to Greve and on the third day to Castellina in Chianti. On the fourth day, your hiking route takes you to the picturesque city of Siena, where you end the day with a wonderful Italian meal. The next day you continue through the vineyards to the wonderful city of towers, San Gimignano. This name hasn’t come out of nowhere, because the landscape of the hill town in Tuscany is characterized by red brick towers. After a restful night, the route takes you to Volterra and finally on the last day of your hiking holiday to the sea at Cecina Mare. With a wonderful glass of Chianti in hand, the journey could not end better than here, on the beautiful coast of Tuscany.

  • Sightseeing in Italy: Right at the beginning of your hiking tour in Tuscany, a particularly worthwhile sight awaits you – the Duomo in Florence, the third largest church in the world and at the same time the most important sight in the city of Florence. From the dome at 107 metres you can enjoy a panoramic view across Florence. Note: Please secure your tickets in advance.
  • Culinary delights in Siena: After a long stroll through Siena and the numerous sights from the Middle Ages, the little streets invite you to taste the culinary delights of Tuscany. There are plenty to try, from wonderful types of wine, pasta, prosciutto or cheese.
  • Picture perfect: The small Italian town of San Gimignano in Tuscany is a truly fantastic sight. The cityscape is characterised by numerous brick towers and so it is not surprising that the historic centre has been a UNESCO World Heritage Site since 1990. A leisurely stroll through the alley of the old town leaves enough time to try one or another regional speciality in the numerous cafés or delicatessens.
  • A visit to the gelato world champion: Something very special awaits all gelato lovers when visiting the small town of San Gimignano – the Gelateria Dondoli on Piazza della Cisterna, one of the best gelateria in the whole country. Whether classic flavours or something unusual, all gelato fans get their money’s worth here.

Even the trip to Florence, the capital of Tuscany and at the same time one of the most beautiful cities in the world, is a delight for the eyes and a small taster of what to expect on your hiking holiday with luggage transfer. Your hiking routes always lead along good hiking trails and paths along the Italian vineyards, forests and hilly areas. The leisure hikes require good basic fitness for the daily stages of around 4 hours. There is always plenty of time to enjoy the beautiful places and unique sights of Tuscany.

In the little streets of Castellina in Chianti
The fountain square in San Gimignano at the evening hour
Hiking in Tuscany overlooking San Gimignano
Book now
To the online version
A hiker rests on a low wall in front of the church of San Leolino, with a view down the valley to the vineyards

Picturesque Tuscany

Florence, medieval villages, wine & Tuscan cuisine

Bestseller
8 Days / 7 Nights
Moderate Walking
145  kg
CO₂-Emissions are offset
145  kg
CO₂-Emissions are offset
145  kg
CO₂-Emissions are offset
A hiker rests on a low wall in front of the church of San Leolino, with a view down the valley to the vineyards

The essentials at a glance

Explore Tuscany's iconic landscapes on this self-guided walking tour from Florence to the Tyrrhenian coast. Discover UNESCO-listed Siena, the medieval towers of San Gimignano, and the Etruscan village of Panzano. Walk through vineyards, olive groves, and pine forests with daily distances of 10-16 km. The route includes wine tasting, transfers between select locations, and accommodation in 3-4 star hotels and agriturismi. Moderate difficulty with up to 4.5 hours walking per day.

Do you have questions about this tour?

Culture, enjoyment and unique scenery in sheer perfection: all of this and lots more awaits you during our hiking holiday in Tuscany. Florence, the pulsating heart of Central Italy, welcomes you in a spectacular fashion: magnificent palaces and cathedrals, David by Michelangelo or the paintings of the great masters such as Leonardo da Vinci and Botticelli. Along remote trails you walk through characteristic Tuscan rolling hills of the Chianti region, via history-charged villages such as Siena and Volterra you proceed further and further towards the Tuscan coast. Along the 'Via Sale' you can already taste the salty sea air on your tongue and once you finally get to dip your tired legs into the turquoise glistening waves of the Tyrrhenian Sea near Cecina Mare, you can be totally sure that you have reached your destination!

  • All information and further tour tips for your hiking holiday in Tuscany.
In the little streets of Castellina in Chianti
The fountain square in San Gimignano at the evening hour
Hiking in Tuscany overlooking San Gimignano
Book now
Book
from
€999
Calculate price
Sophia Altenberger
Sophia Altenberger
+43 6219 60877 184
Contact form
Book an appointment

Our eight-day hiking tour in Tuscany takes you in six daily stages from inland to the Tyrrhenian Sea. The starting point of your hiking holiday and the beginning of countless active experiences is Florence, the capital of Tuscany. Here it is not difficult to immediately immerse yourself in the Italian flair and the Mediterranean lifestyle. The journey takes you through the unmistakable landscape first to Greve and on the third day to Castellina in Chianti. On the fourth day, your hiking route takes you to the picturesque city of Siena, where you end the day with a wonderful Italian meal. The next day you continue through the vineyards to the wonderful city of towers, San Gimignano. This name hasn’t come out of nowhere, because the landscape of the hill town in Tuscany is characterized by red brick towers. After a restful night, the route takes you to Volterra and finally on the last day of your hiking holiday to the sea at Cecina Mare. With a wonderful glass of Chianti in hand, the journey could not end better than here, on the beautiful coast of Tuscany.

  • Sightseeing in Italy: Right at the beginning of your hiking tour in Tuscany, a particularly worthwhile sight awaits you – the Duomo in Florence, the third largest church in the world and at the same time the most important sight in the city of Florence. From the dome at 107 metres you can enjoy a panoramic view across Florence. Note: Please secure your tickets in advance.
  • Culinary delights in Siena: After a long stroll through Siena and the numerous sights from the Middle Ages, the little streets invite you to taste the culinary delights of Tuscany. There are plenty to try, from wonderful types of wine, pasta, prosciutto or cheese.
  • Picture perfect: The small Italian town of San Gimignano in Tuscany is a truly fantastic sight. The cityscape is characterised by numerous brick towers and so it is not surprising that the historic centre has been a UNESCO World Heritage Site since 1990. A leisurely stroll through the alley of the old town leaves enough time to try one or another regional speciality in the numerous cafés or delicatessens.
  • A visit to the gelato world champion: Something very special awaits all gelato lovers when visiting the small town of San Gimignano – the Gelateria Dondoli on Piazza della Cisterna, one of the best gelateria in the whole country. Whether classic flavours or something unusual, all gelato fans get their money’s worth here.

Even the trip to Florence, the capital of Tuscany and at the same time one of the most beautiful cities in the world, is a delight for the eyes and a small taster of what to expect on your hiking holiday with luggage transfer. Your hiking routes always lead along good hiking trails and paths along the Italian vineyards, forests and hilly areas. The leisure hikes require good basic fitness for the daily stages of around 4 hours. There is always plenty of time to enjoy the beautiful places and unique sights of Tuscany.

In the little streets of Castellina in Chianti
The fountain square in San Gimignano at the evening hour
Hiking in Tuscany overlooking San Gimignano

Itinerary at a glance

The cathedral in Florence is an absolute must-see, but Tuscany has even more to offer: San Gimignano is the city of towers, the Etruscan village of Panzano and the Monte Nero nature reserve. On top of that, a Chianti on the Thyrrhenian Sea!

Walk along the traces of the Medici through gorgeous alleyways and across the bridge Ponte Vecchio to the Piazza della Signoria – the centre and heart of the old part of town.

Hotel example: De la Pace

Your first hiking tour warms the cockles of your heart straight away with all Tuscany has to offer with regards to classical dreamscape: vineyards and forests, as well as old stone houses and high rising cypresses avenues line your way – Tuscany picture-perfect. Greve in Chianti invites you to explore the ‚Laubengänge‘-arcades on the lively Piazza.

Hotel example: Albergo del Chianti

Along remote forest paths you walk past numerous wine-growing estates towards Panzano, a little Etruscan hamlet worth visiting. Then through golden corn fields and via vineyards onwards to Lucarelli, before you take a short bus ride and reach the Medieval Castellina with its historic town wall.

Hotel example: Il Colombaio

Along pilgrims‘ tracks the route leads you along the Via Romea only along a segment of it towards the eternal city. Your Day Finish is the charming town of Siena, renowned for the traditional horse race ‚Palio‘, numerous fantastically preserved city gates dating back to the Middle Ages as well as red-brick buildings along the semi-circular Piazza del Campo.

Hotel example: Hotel Minerva

Today you are off to Valle Col d´Elsa. Explore the historic fortress complex and marvel at the Medieval architecture of Colle, before you proceed through vineyards and along roaring rivers to the „Manhattan of Tuscany“. Your Day Finish is called San Gimignano, this nick name is due to its silhouette reminding us of a skyline. Take a stroll through the many little alleyways and marvel at the seemingly countless number of towers.

Hotel example: La Cisterna

In the Monte Nero nature reserve you discover green forests and the ‚Cascate della Strolla‘, a little waterfall with crystal-clear water. The ancient salt trade route Via del Sale leads you directly to the alabaster-city Volterra, on your way you pass ancient Etruscan grave chambers that are worth a visit. Discover the Medieval belfry rising high above the city, the panoramic views over the old part of town will fittingly rewards your efforts.

Hotel example: San Lino

As a finale to your hiking week the Tuscan coast awaits with an extensive hiking tour through the Pineta of Cecina, a giant pine tree grove with numerous entwined paths and tracks. Enjoy your final evening in Tuscany with a glass of Chianti looking out onto the turquoise glistening of the Tyrrhenian Sea, whilst the two islands Elba and La Gorgona quietly sink into the sea at the horizon in the crimson evening sun.

Hotel example: Hotel Golden Residence

Day
08

Departure or extension

Itinerary at a glance

The cathedral in Florence is an absolute must-see, but Tuscany has even more to offer: San Gimignano is the city of towers, the Etruscan village of Panzano and the Monte Nero nature reserve. On top of that, a Chianti on the Thyrrhenian Sea!

Walk along the traces of the Medici through gorgeous alleyways and across the bridge Ponte Vecchio to the Piazza della Signoria – the centre and heart of the old part of town.

Hotel example: De la Pace

Your first hiking tour warms the cockles of your heart straight away with all Tuscany has to offer with regards to classical dreamscape: vineyards and forests, as well as old stone houses and high rising cypresses avenues line your way – Tuscany picture-perfect. Greve in Chianti invites you to explore the ‚Laubengänge‘-arcades on the lively Piazza.

Hotel example: Albergo del Chianti

Along remote forest paths you walk past numerous wine-growing estates towards Panzano, a little Etruscan hamlet worth visiting. Then through golden corn fields and via vineyards onwards to Lucarelli, before you take a short bus ride and reach the Medieval Castellina with its historic town wall.

Hotel example: Il Colombaio

Along pilgrims‘ tracks the route leads you along the Via Romea only along a segment of it towards the eternal city. Today's destination is the charming town of Siena, renowned for the traditional horse race 'Palio', numerous fantastically preserved city gates dating back to the Middle Ages as well as red-brick buildings along the semi-circular Piazza del Campo.

Hotel example: Hotel Minerva

Today you are off to Valle Col d'Elsa. Explore the historic fortress complex and marvel at the Medieval architecture of Colle, before you proceed through vineyards and along roaring rivers to the “Manhattan of Tuscany”. Your day finish is called San Gimignano, this nick name is due to its silhouette reminding us of a skyline. Take a stroll through the many little alleyways and marvel at the seemingly countless number of towers.

Hotel example: La Cisterna

In the Monte Nero nature reserve you discover green forests and the 'Cascate della Strolla', a little waterfall with crystal-clear water. The ancient salt trade route Via del Sale leads you directly to the alabaster-city Volterra, on your way you pass ancient Etruscan grave chambers that are worth a visit. Discover the Medieval belfry rising high above the city, the panoramic views over the old part of town will fittingly rewards your efforts.

Hotel example: San Lino

As a finale to your hiking week the Tuscan coast awaits with an extensive hiking tour through the Pineta of Cecina, a giant pine tree grove with numerous entwined paths and tracks. Enjoy your final evening in Tuscany with a glass of Chianti looking out onto the turquoise glistening of the Tyrrhenian Sea, whilst the two islands Elba and La Gorgona quietly sink into the sea at the horizon in the crimson evening sun.

Hotel example: Hotel Golden Residence

Day
08

Departure or extension

Other variations of this tour

Hiker in front of vines near San Gimignano with rolling hills in the background
Picturesque Tuscany with Charm
8 Days
Vineyards in Greve in Chianti
Tuscan house with a charming garden in San Gimignano
Volterra
Beach path at cecina
Coast of Cecina Mare
Sunset at Cecina Mare beach

Difficulty level

Moderate Walking

You always walk on well-maintained hiking paths, gravel paths and trails. Daily routes mostly lead you along vineyards, forests and through soft rolling landscape. A good basic fitness level is sufficient for walking times of up to 4.5 hours maximum, there is plenty of time to enjoy the cultural highlight of the one of a kind region in peace and quiet.

Difficulty level

Moderate Walking

You always walk on well-maintained hiking paths, gravel paths and trails. Daily routes mostly lead you along vineyards, forests and through soft rolling landscape. A good basic fitness level is sufficient for walking times of up to 5 hours maximum, there is plenty of time to enjoy the cultural highlight of the one of a kind region in peace and quiet.

Prices & Dates

Prices per person in EUR

Services & Information

Further details about this tour

Included

  • Accommodation in 3***- and 4****-hotels as well as beautiful italian lodges ‘Agriturismi’ (partly with pool)
  • Breakfast
  • Luggage transfer
  • 1 Transfer San Gimignano – Ulignano
  • 1 Transfer Volterra – Cecina
  • Bus rides according to program
  • 1 Wine tasting
  • Welcome briefing
  • Digital travel documents incl. navigation app, GPS-data, route book
  • Service hotline

Optional

  • Printed route book, per room EUR 20

Arrival / Parking / Departure

  • Arrival by train to Florence (www.trenitalia.com)
  • Florence airport and by train to the center, duration approx. 20 minutes (www.gestramvia.it)
  • Parking: Public parking spaces near the hotel, costs approx. EUR 20 per day. Public parking spaces on the outskirts of the city, costs approx. EUR 20 per week. Public garage, costs approx. EUR 140 per week
  • Departure by bus to the train station Cecina and by train to Florence, duration approx. 3 hours (www.at-bus.it, www.trenitalia.com)

Things to note

  • Tourist tax, if due, is not included in the price

Services & Information

Further details about this tour

Included

  • Accommodation in 3***- and 4****-hotels as well as italian lodges ‘Agriturismi’ (partly with pool)
  • Breakfast
  • Luggage transfer
  • Transfers Florence – Gabbiano, San Gimignano – Ulignano and Volterra – Cecina
  • 1 transfer Volterra – Cecina
  • Bus rides according to program
  • 1 wine tasting
  • Welcome briefing
  • Digital travel documents incl. navigation app, GPS-data, route book
  • Service hotline

Optional

  • Printed route book, per person EUR 20

Arrival / Parking / Departure

  • Arrival by train to Florence (www.trenitalia.com)
  • Florence airport and by train to the center, duration approx. 20 minutes (www.gestramvia.it)
  • Parking: Public parking spaces near the hotel, costs approx. EUR 20 per day. Public parking spaces on the outskirts of the city, costs approx. EUR 20 per week. Public garage, costs approx. EUR 140 per week
  • Departure by bus to the train station Cecina and by train to Florence, duration approx. 3 hours (www.at-bus.it, www.trenitalia.com)

Things to note

  • Tourist tax, if due, is not included in the price.

Travel stories for this tour

Personally on site for you

Woman hiking through green vineyard rows in Tuscany with cypress-lined hills and historic buildings visible in the background under blue sky.
Team on Tour
Travel Story: On Foot Through Picturesque Tuscany
New year, new journey—but this time, I wanted to try something different. Over the past two years, I’ve explored Italy by bike, sharing my experiences from Bolzano to Venice and from Pisa to Florence. Italy is, without a doubt, one of my favorite destinations in Europe. This year, however, I’m leaving the bike at home. Instead, I’m packing my hiking boots and my dear friend, Robert. We are both so excited to experience the picturesque Tuscan landscape up close and on foot. Robert and I have one big thing in common: we love great food and are "active foodies" through and through. Between the stress of home renovations and the daily grind of a construction site, this was going to be the special getaway we’d been looking forward to for months.  Our journey takes us from one stunning city to the next, straight through the lush greenery of Tuscan wine country, all the way to the Tyrrhenian Sea.
Sunset in Volterra
Team on Tour
Travel story: From the cultural city of Florence to vast sceneries all the way to the sea
Via picturesque vineyards, through olive groves with endless distant views, you proceed from the capital of Tuscany all the way to the coast to the sandy beach in Cecina. Within 8 days we hike through the impressive landscape of Tuscany and stop in charming small and large towns. We are enchanted by the Tuscan cuisine and excited about Tuscan hospitality. This hiking holiday leaves nothing to be desired!
Sophia Altenberger

"We look forward to making your holiday dreams come true"

Sophia Altenberger
Travel Specialist
One call to vacation bliss
+43 6219 60877 184
Monday - Friday: 9.00 AM - 6.00 PM
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Sustainably on the go

Our contribution to climate protection

  • Active vacations are among the most environmentally friendly and healthiest ways to travel. Traveling on foot means moving in a climate-conscious way while conserving resources.

  • Our carefully selected accommodations, like us, are committed to lived sustainability. They are deeply rooted in their regions, work with local suppliers, provide attractive employment opportunities for local residents, and thereby strengthen local value creation.

  • With the Eurohike On Tour app, we offer a digital version of our travel documents, allowing you to navigate confidently while on the road. By moving to digital formats, we help conserve valuable natural resources.

  • Eurohike has been certified as a sustainable tour operator with the internationally recognized Travelife certification. To achieve this, more than 261 requirements were carefully met.

  • Even though hiking vacations (and cycling vacations with Eurobike) are among the most climate-friendly forms of travel, they still generate CO₂ emissions. These are carefully measured using the “Carmacal” calculator. Through our commitment to selected climate protection projects, we aim to give something back to the environment.

    145 kg
    CO₂-Emissions are offset

    Accommodation (51%)

    Meals (22%)

    Transport (27%)

    145 kg
    CO₂-Emissions are offset

    Accommodation (51%)

    Meals (22%)

    Transport (27%)

    145 kg
    CO₂-Emissions are offset

    Accommodation (51%)

    Meals (22%)

    Transport (27%)

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