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Hiker in front of vines near San Gimignano with rolling hills in the background

Picturesque Tuscany with Charm

Florence, medieval villages, wine & Tuscan cuisine

New tour
8 Days / 7 Nights
Moderate Walking
Hiker in front of vines near San Gimignano with rolling hills in the background

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.

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.

Itinerary at a glance

On your way from the Renaissance city of Florence to the Tyrrhenian Sea, you will encounter UNESCO World Heritage Sites such as San Gimignano or Siena with their historic old towns. You will always be accompanied by cypresses, pine trees, olive groves and vineyards, which characterise the typical and dreamlike landscape of Tuscany.

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.

After a short transfer to Machico, you will walk along the impressive north coast on one of the old supply routes, which was previously used to cultivate the vineyards. Today one of the nicest footpaths runs along this route to Porto da Cruz. Enjoy the breath-taking views.

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.

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.

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.

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.

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. Feel the golden sandy beach under your feet. Today you will spend the night directly by the sea. Enjoy your last evening in Tuscany with a view of the islands of Elba and La Gorgona on the horizon.

Departure or extension

Other variations of this tour

Route Information

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.

Prices & Dates

You spend the night in specially selected hotels with special "extras" and can enjoy all the facilities of the charming accommodations (see "Accommodation").

Prices per person in EUR

Services & Information

Further details about this tour


  • Accommodation as already mentioned
  • Breakfast
  • Luggage transfer
  • Welcome briefing (German, English)
  • 1 Wine tasting (English)


  • 1 Transfer San Gimignano – Ulignano
  • Bus rides according to the program
  • Carefully elaborated route description
  • Detailed travel documents 1x per room (German, English, French)
  • App for Navigation and GPS-data
  • Service hotline

Arrival / Parking / Departure

  • Florence airport. By bus in about 30 minutes to the main train station or you can take a short taxi ride, approx. EUR 25 per journey.
  • Parking: Public parking spaces near the hotel, approx. EUR 70 per week. Public car park at the edge of the city, approx. EUR 20 per week. Underground parking spaces approx. EUR 20 to EUR 36 per day. Payable on spot, no reservation in advance possible.
  • Return journey from Marina di Castagneto via Castagneto Carducci to Florence

Things to note

  • Tourist tax, if due, is not included in the price
  • Special dates on request
  • Further important information according to the package travel law can be found here!

Join us in achieving greater sustainability by choosing our digital route book, rather than the printed version. As a small thank you we will give you a discount of €20 per room.


Relax in one of our charming accommodations along your walking tours.

Verena Winkler

"I look forward to making your vacation dreams come true."

Verena Winkler
Travel Specialist
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