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Tuscany Highlights

Florence, Chianti wines and the Tuscany Coast

Culture, enjoyment and unique landscapes in perfection: all this and much more await you on our long-distance walking tour of Tuscany. Florence, the beating heart of central Italy. Michelangelo's David or the paintings of great masters such as Leonardo da Vinci and Botticelli. On deserted paths, you walk through the typical Tuscan hilly landscape of the Chianti region, and via historic places such as Siena and Volterra and continue towards the Tuscan coast.

Details about the hiking tour Picturesque Tuscany

Our eight-day hiking tour in Tuscany takes you from the interior to the Tyrrhenian Sea in six stages. The starting point of your walking holiday and the beginning of countless active experiences and discoveries is Florence, the capital of Tuscany.

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 walking route will take you to the picturesque city of Siena, where you can end the day with a delicious Italian dinner. The next day you will continue through the vineyards to the beautiful tower town of San Gimignano. The journey takes you to Volterra and finally on the last day of your walking holiday to the sea to Cecina Mare.

The highlights of the walking holiday at a glance

  • Duomo in Florence: The third largest church in the world and at the same time the most important landmark in the city of Florence. From the dome, at 107 meters in height, you can enjoy a beautiful panoramic view far over Florence.

  • Siena: The small streets and delicacies invite you to taste the culinary delights of Tuscany - there are plenty of delicacies to try, from delicious varieties of wine, pasta, prosciutto or cheese

  • San Gimignano: The cityscape is characterised by numerous brick towers and it is therefore not surprising that the historic centre has been on the UNESCO World Heritage List since 1990.

  • Famous ice creams: Something very special awaits all ice cream lovers in the small town of San Gimignano - the Gelateria Dondoli in Piazza della Cisterna, one of the best ice cream parlours in the whole country.

Worth knowing about the walking holiday in Tuscany

Your walking routes always lead on good footpaths and paths along the Italian vineyards, forests and hilly areas. The pleasure walks require a good basic condition for the daily stages of about 4 hours. There is always enough time to enjoy the beautiful places and unique sights of Tuscany.

Route summary

On quiet paths, you will go through the typical Tuscan hilly landscape of the Chianti region, via historical places like Siena and Volterra you will reach further and further towards the Tuscan coast. On the Via Sale, you can already taste the salty air of the sea on your tongue and when you finally hold your tired hiking legs in the glittering turquoise waves of the Tyrrhenian Sea at Cecina Mare, you are quite sure: you have reached your destination!

This tour has been graded as Medium. Find out more about our walking holiday difficulty levels.

Tour information
Medium
  • 8 Days / 7 Nights
  • Self-Guided
  • Luggage transfers included
  • Total walking distance: approx. 72 km
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Itinerary

Individual arrival in Florence, one of the most famous art cities in the world. This Renaissance city is a large open-air museum with its Duomo, Ponte Vecchio and countless palazzos. Walk in the footsteps of the Medici through beautiful alleys to Piazza della Signoria - the centre and heart of the historic old town. Visit Santa Maria Novella, this Gothic-style church has a monastic pharmacy, Antica Farmacia Santa Maria Novella. Inside you imagine yourself 800 years back in time, old recipes are still sold here. After a busy day, you can relax on one of the many terraces of Piazza della Repubblica, also known as the living room of Florence, also very popular with Florentines. Famous drinking places are Gilli, Paszkovski and Caffè Le Giube Rosse.

Your first hiking stage will delight the heart of you as a hiker with all that Tuscany has to offer in a classic dream landscape. Forests, olive groves and vineyards, historic walled towns and winding roads with tall cypresses cross your path, Tuscany like out of a picture book. The gateway to Chianti, Greve in Chianti, invites you to explore the arcades in the lively square. This lively town is famous for its specially shaped pizzas and the market square with its large porticos and the bronze statue of Giovanni da Verrazzano; discoverer of New York harbour. In the large porticos, you will find wine bars, restaurants and the wine museum.

ca. 4 hours
11 km
400 m
300 m

A serene silence accompanies you along deserted forest paths, vines and grapes as far as the eye can see. You will pass numerous wineries as you walk towards Panzano in Chianti, a popular small village from the Etruscan period with the castle of Panzano and the Pieve di San Leolino church which are well worth a visit. Take a short break and stroll through the medieval streets, soak up the atmosphere and enjoy a glass of Chianti wine in one of the bars in the square. Would you like something tasty for the road? Then drop by Antica Macelleria Cecchini; a butcher's shop known for its Florentine steak. During the ministry, passages from Dante's Divine Comedy are recited.

Through golden wheat fields and vineyards to the tiny village of Lucarelli, before a short bus ride to your destination of today, medieval Castellina with its historic city wall. Strategically located in the middle of the region, with the castle Rocca and the impressive tunnel; Via delle Volte offers you breathtaking views. In Castellina, you can enjoy a glass of Chianti wine in one of the many wine bars and also taste the unforgettable taste of salami and other cold cuts at one of the butchers.

ca. 4 hours
11 km
350 m
300 m

Following in the footsteps of the pilgrims, the road leads you along the Via Romea pilgrimage route, just a short part of the route to the Eternal City. Your final destination today is the enchanting city of Siena, famous for the traditional Palio horse race between the seventeen districts and the famous circular square Piazza del Campo. The countless fantastically preserved city gates from the Middle Ages, are the historic centre of Unesco's World Heritage List. Famous movies like Letters to Juliet and James Bond's Quantum of Solace have scenes shot here. The Duomo di Siena is home to many cultural treasures including a life-size copy of The Last Supper in stained glass. After all those impressions it is wonderful to take a breather in the park Orto dei Tolomei, this higher garden offers an incredibly beautiful view over Siena. 

ca. 4,5 hours
16 km
300 m
500 m

Today we head to the unusual but beautifully built town of Valle Col d´Elsa. Explore the historic fortress and admire the medieval architecture of Colle. Stroll through rolling vineyards and olive groves, with the occasional hamlet or farm with an imposing cypress avenue. Stunning views guide you along rushing rivers to the distinctive towers of San Gimignano, nicknamed "Manhattan of Tuscany" for its skyline-like silhouette. Fourteen towers remain of the seventy-two that were once built in the Middle Ages. Stroll through the many small alleys and admire the seemingly endless towers and eat ice cream at Gelato World Champion, Dondoli in Piazza della Sisterna.

ca. 4 hours
13 km
350 m
250 m

In the Montenero Reserve, you will discover green forests and the Strolla River which crosses the Nature Reserve creating a series of charming waterfalls with lush vegetation including the "Cascate della Strolla", a small waterfall with crystal clear waters. The ancient salt trade route Via del Sale leads you to the perfectly preserved city wall “Porta Etrusca” of Volterra. The 7 km long city wall from the 4th century BC houses numerous Etruscan tombs and urns. There are no more beautiful Tuscan towns than Volterra, situated on top of a hill and surrounded by impressive cliffs and rolling green hills. Explore the Roman theatre and the medieval bell tower Palazzo dei Priori, the panoramic view over the old town will reward you for it.

Tip: Dine at Ristorante da Beppino for the best pasta experience in all of Tuscany. They even have a small pastificio (pasta factory) next to the restaurant where they make all the pasta, gnocchi and ravioli themselves.

ca. 4 hours
11 km
500 m
250 m

At the end of your hiking week, the Tuscan coast awaits you with an extended walk through the Pineta of Cecina, a huge pine forest with countless winding paths and paths, ending in a long line of dunes over many kilometres of beautiful sandy beaches. Enjoy your last evening in Tuscany with a glass of Chianti overlooking the turquoise glitter of the Tyrrhenian Sea, while the twin islands of Elba and La Gorgona sink gently into the red of the evening sun on the horizon.

ca. 3 to 4 hours
10 km
0 m
0 m

Your walking holiday ends after breakfast, but you can of course postpone the farewell and make more wine memories by extending your trip.

Route information

You always walk on good footpaths and unpaved paths. The daily routes pass through vineyards, forests and rolling hills. Some basic condition is sufficient for walking times of up to 4.5 hours, there is enough time to enjoy the cultural highlights of this unique region in peace.

Prices and dates

Prices are per person in GBP and exclude flights


Complete a Booking Request: Tuscany Highlights

Prices and services may vary depending on the travel year
Select travel year:
Place of arrival: Florence
  Season 1
01.04.2023 - 22.04.2023
17.09.2023 - 07.10.2023

Sunday
Season 2
23.04.2023 - 20.05.2023
03.09.2023 - 16.09.2023

Sunday
Season 3
21.05.2023 - 02.09.2023

Sunday
Tuscany Highlights, IT-TOWFC-08X
Base price
829.00
879.00
939.00
Single room surcharge 289.00 289.00 289.00
  • You will stay in beautiful 3*** and 4**** Hotels and beautiful Italian country houses "Agriturismo", some with swimming pool
Season 1
Apr 1, 2023 - Apr 22, 2023
Sep 17, 2023 - Oct 7, 2023
Sunday
Season 2
Apr 23, 2023 - May 20, 2023
Sep 3, 2023 - Sep 16, 2023
Sunday
Season 3
May 21, 2023 - Sep 2, 2023
Sunday
Tuscany Highlights, IT-TOWFC-08X
Base price
Single room surcharge
829.00
289.00
879.00
289.00
939.00
289.00
  • You will stay in beautiful 3*** and 4**** Hotels and beautiful Italian country houses "Agriturismo", some with swimming pool
Season 1
Apr 1, 2023 - Apr 22, 2023
Sep 17, 2023 - Oct 7, 2023
Season 2
Apr 23, 2023 - May 20, 2023
Sep 3, 2023 - Sep 16, 2023
Season 3
May 21, 2023 - Sep 2, 2023
Florence
Double room p.p.
Single room surcharge
Cecina Mare/surroundings
Double room p.p.
Single room surcharge
85.00
69.00
75.00
39.00
95.00
69.00
89.00
39.00
95.00
69.00
89.00
39.00
Additional nights
Place of arrival: Florence
  Season 1
Apr 1, 2023 - Apr 22, 2023
Sep 17, 2023 - Oct 7, 2023

Sunday
Season 2
Apr 23, 2023 - May 20, 2023
Sep 3, 2023 - Sep 16, 2023

Sunday
Season 3
May 21, 2023 - Sep 2, 2023

Sunday
Florence
Double room p.p. 85.00 95.00 95.00
Single room surcharge 69.00 69.00 69.00
Cecina Mare/surroundings
Double room p.p. 75.00 89.00 89.00
Single room surcharge 39.00 39.00 39.00
Prices per person in GBP

Services / Information

Services

Including

  • 7 nights as described, including breakfast
  • Wine tasting (English)
  • Transfer San Gimignano-Ulignano
  • Personal welcome meeting (German, English)
  • Luggage transfer(s) max. 1 piece of luggage 20 kg per person
  • Travel folder 1 x per room (German, English with route and overview maps, detailed route description, places of interest, important telephone numbers, luggage labels)
  • GPS data available on request
  • Service Hotline

Not included

  • Tourist tax, if applicable, to be paid locally
  • Bus rides Florence-Gabbiano, Lucarelli-Castellina, Siena-Colle Val d´Elsa, Saline/Volterra-Cecina, approximately €15 per person
Arrival information
  • Airport: Florence Airport, from there by bus, approx. 30 min. to the central station or a short taxi ride, approx. €25 per journey
  • Train: Florence Station
  • Parking: Limited number of free hotel parking spaces or public parking spaces near the hotel, approximately €70 per week. Public parking on the outskirts of town approx. €20-36 per week. To be paid on-site, reservation is not possible

 

  • Departure: Return journey from Cecina Mare to Cecina by bus, from there by train to Florence, duration approx. 2 hours
Sample hotel list

This is a sample hotel list. Hotels will be booked depending on availability.

Florence

Hotel De La Pace 3***

http://de-la-pace.florence-hotels-it.com/de/

Greve in Chianti

Albergo del Chianti 3***

www.albergodelchianti.it

Castellina in Chianti

Albergo il Colombaio 3***

www.albergoilcolombaio.it

Siena

Hotel Minerva 3***

www.albergominerva.it

San Gimignano

La Cisterna 3***

www.hotelcisterna.it

Volterra

San Lino 4****

www.hotelsanlino.net

Cecina Mare

Hotel Stella Marina 3***

www.hotel-stella-marina.it

 

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