Scheduled Trekking

Valle d'Aosta
Hiking in Italy
Toscana - Firenze (Fi)

The Via Francigena between Florence and Siena
Guided hiking holiday

Toscana - Firenze (Fi)

Monday 10 - Thursday 20 May 2027

11 days | 10 night

10 places available

Hiking through the Tuscan countryside in the footsteps of pilgrims


The Via Francigena, a historic route travelled since the Middle Ages, that runs from Canterbury to Rome, will take us from near Florence to Siena through the Tuscan countryside. The landscape is unique, with gentle rolling hills dotted with wheat fields, vineyards, and olive orchards, walled villages on hilltops, isolated farmhouses and castles. History and culture are centuries-old: pilgrims, clergy and merchants have travelled this route on their way to and from Rome, stopping at remote monasteries, praying in churches, exchanging goods in market squares. Even today, the route is travelled by pilgrims, who stay in restored monasteries and parish halls and take part in local prayer services. Walking along dirt roads flanked by cypress and paths in the woods, we will enjoy beautiful views, visit medieval citadels and ancient churches, enjoy hearty meals in local restaurants, and taste world-famous local wines.

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Day by day program | Guided hiking holiday

Mon, May 10 (day 1)

Florence

We will meet in Florence in the early afternoon. After an introductory briefing, we will go for a walk through this magnificent city with its famous churches and palaces, the Ponte Vecchio, and the Arno river, reaching a beautiful viewpoint above the city. We will cap our first day with a welcome dinner (Note: we will see the monuments from the outside but will not go inside.)
Meet at the hotel in Florence in the early afternoon
Afternoon walk through the city to Piazzale Michelangelo
Welcome dinner
Walk: Approximately 6 km, +100 m elevation gain, - 100 m elevation loss

Night in Florence (-, -, D)

Tue, May 11 (day 2)

San Miniato - Gambassi Terme

After a brief transfer, we will begin our hike through the rolling hills. A trail of extraordinary beauty will lead us along the hilltops of Val d’Elsa. Following the itinerary of Archbishop Sigeric of Canterbury, who in 990 travelled back from Rome and wrote the oldest surviving diary about the Via Francigena, we will come across two submansiones, as Sigeric called the stops on his route: the Pieve di Coiano, with its steep stone steps, and the Pieve di Santa Maria a Chianni, rebuilt in the XII century. Shortly after, we will reach Gambassi, famous for its thermal waters.After a brief transfer, we will begin our hike through the rolling hills. A trail of extraordinary beauty will lead us along the hilltops of Val d’Elsa. Following the itinerary of Archbishop Sigeric of Canterbury, who in 990 travelled back from Rome and wrote the oldest surviving diary about the Via Francigena, we will come across two submansiones, as Sigeric called the stops on his route: the Pieve di Coiano, with its steep stone steps, and the Pieve di Santa Maria a Chianni, rebuilt in the XII century. Shortly after, we will reach Gambassi, famous for its thermal waters.
Hike San Miniato fraz. Canneto-Gambassi Terme
Picnic lunch
Dinner in Gambassi Terme
Private transfer to the outskirts of the town of San Miniato (40 km, approx 1 hour)Hike: 18.5 km, +450 m, -250 m

Night in Gambassi Terme (B, L, D)

Wed, May 12 (day 3)

Gambassi Terme - San Gimignano

The route goes through hills and woods before reaching the church of Pancole and the monastery at Cellole, places of peace and serenity. The towers of San Gimignano will soon appear. We will spend two nights in the town and get a chance to visit its cathedral, city hall, and fortress, and taste some local delicacies.
Hike Gambassi Terme-San Gimignano
Picnic lunch
Walk through San Gimignano
Dinner
Hike: 13.5 km, +/-350 m

Night in San Gimignano (B, L, D)

Thu, May 13, (day 4)

San Gimignano - Colle Val d’Elsa

From San Gimignano, the route heads south into what is considered one of the most beautiful sections of the Via Francigena. The trail goes up and down into the valley carved by the river Foci, which we will cross near the Molino d’Aiano. The trail then takes us to Colle Val d'Elsa, whose cathedral guards a venerated relic and which is famous for its glass production. A short transfer will take us back to San Gimignano. Dinner tonight is on your own.
Hike San Gimignano-Colle Val d'Elsa
Picnic lunch
Transfer to San Gimignano
Hike: 14.1 km, +260 m, -460 m
Transfer: Approx. 15 minutes

Night in San Gimignano (B, L, -)

Fri, May 14 (day 5)

Colle Val d’Elsa - Monteriggioni

Today's stage will take us to several ancient churches and abbeys. After a brief transfer back from San Gimignano to Colle Val d'Elsa, we will follow the river Elsa along a beautiful stretch with ponds and waterfalls and then continue past a hot spring to the Romanesque church of San Martino di Strove. Our next destination will be the village of Abbadia a Isola, where we will stop for the night at a restored abbey, experiencing the kind of simple but warm hospitality that pilgrims enjoy. We will be in sight of the town of Monteriggioni, with its unmistakable fortified walls and towers atop the hill.Today's stage will take us to several ancient churches and abbeys. After a brief transfer back from San Gimignano to Colle Val d'Elsa, we will follow the river Elsa along a beautiful stretch with ponds and waterfalls and then continue past a hot spring to the Romanesque church of San Martino di Strove. Our next destination will be the village of Abbadia a Isola, where we will stop for the night at a restored abbey, experiencing the kind of simple but warm hospitality that pilgrims enjoy. We will be in sight of the town of Monteriggioni, with its unmistakable fortified walls and towers atop the hill.
Transfer to Colle Val d'ElsaHike Colle Val d'Elsa-Abbadia Isola-Monteriggioni
Picnic lunch
DinnerTransfer: Approx. 15 minutes
Hike: 16.5 km, +380 m, -270 mTransfer: Approx. 15 minutes

Night in Monteriggioni (B, L, D)

Sat, May 15 (day 6)

Monteriggioni - Siena

After visiting Monteriggioni, with its half a mile of medieval walls and 14 towers, we will embark on the last section of the route to Siena. With the walled city behind us, we will follow the white trails of Siena's countryside to the ancient medieval village of Cerbaia. We will walk through woodland to reach the Castello della Chiocciola and the Castello di Villa, before hiking down into the reclaimed riverbed of Pian del Lago, once a swamp. After stopping at the abbey of San Leonardi and crossing the woods of Renai, we will get to Porta Camollia, the traditional Via Francigena gate to the city of Siena.After visiting Monteriggioni, with its half a mile of medieval walls and 14 towers, we will embark on the last section of the route to Siena. With the walled city behind us, we will follow the white trails of Siena's countryside to the ancient medieval village of Cerbaia. We will walk through woodland to reach the Castello della Chiocciola and the Castello di Villa, before hiking down into the reclaimed riverbed of Pian del Lago, once a swamp. After stopping at the abbey of San Leonardi and crossing the woods of Renai, we will get to Porta Camollia, the traditional Via Francigena gate to the city of Siena.
Hike Monteriggioni-Siena
Picnic lunch
Dinner
Hike: 20.5 km, +330 m, -250 m

Night in Siena (B, L, D)

Sun, May 16 (day 7)

Siena

A day to rest and enjoy Siena's treasures: the slanted Piazza del Campo where the famous Palio horse race is held, the civic museum with its XIV-century frescoes, the Torre grossa with its fabulous view, the cathedral, the museum of Santa Maria della Scala, once one of the oldest and largest hospitals in Europe, and any of the other museums. Lunch is on your own in one of the many restaurants and cafes in town.A day to rest and enjoy Siena's treasures: the slanted Piazza del Campo where the famous Palio horse race is held, the civic museum with its XIV-century frescoes, the Torre grossa with its fabulous view, the cathedral, the museum of Santa Maria della Scala, once one of the oldest and largest hospitals in Europe, and any of the other museums.
Lunch is on your own in one of the many restaurants and cafes in town.

Night in Siena (B, -, D)

Mon, May 17 (day 8)

Sant'Antimo - Castelnuovo dell'Abate

Our next day of hiking will lead us to discover the nicest Benedictine abbey of Tuscany. A brief transfer will take us to Montalcino, from where we will hike to Sant'Antimo, an ancient abbey immersed in the peaceful countryside. We will return to Montalcino in the afternoon with time for a brief visit of the town.
Private transfer to Montalcino
Hike Montalcino-Castelnuovo dell'Abate
Picnic lunch
Bus to Montalcino
Hike: 9 km, + 175 m, -340 m
Transfers: Approx 1 hour each way

Night in Montalcino (B, L, D)

Tue, May 18 (day 9)

Montalcino - San Quirico d'Orcia

The hike from Montalcino to San Quirico d'Orcia is a stunning trek through the heart of the Val d'Orcia in Tuscany. You will walk past world-famous vineyards, golden grain fields, and iconic cypress tree groves, another beautiful ancient town in the world-renowned Val d'Orcia. At the arrival time to walking through San Quirico ancient stone streets, explore historic gems like the Romanesque Collegiate Church and the beautiful Renaissance gardens of Horti Leonini.The hike from Montalcino to San Quirico d'Orcia is a stunning trek through the heart of the Val d'Orcia in Tuscany. You will walk past world-famous vineyards, golden grain fields, and iconic cypress tree groves, another beautiful ancient town in the world-renowned Val d'Orcia. At the arrival time to walking through San Quirico ancient stone streets, explore historic gems like the Romanesque Collegiate Church and the beautiful Renaissance gardens of Horti Leonini.
Hike 13 km, +260 m, -380 m
Bus to Montalcino

Night in Montalcino (B, L, D)

Wed, May 19 (day 10)

San Quirico d'Orcia-Pienza-Montepulciano

The hike from San Quirico d'Orcia to Pienza is a breathtaking journey through the heart of the UNESCO-listed Val d'Orcia, leading you along scenic dirt roads lined with iconic cypress trees. As you follow this historic trail, you will experience the quintessential Tuscan landscape of rolling clay hills and golden fields that look like a living painting. The gently climbing route culminates in a rewarding arrival at Pienza, the "ideal Renaissance city," famous for its stunning architecture and delicious Pecorino cheese.
Hike: 9 km, + 275 m, -200 m
Bus from/to Montalcino

Night in Montalcino (B, L, D)

Thu, May 20 (day 11)

Departure

After breakfast we will transfer by private van back to Florence and enjoy our final dinner together.After breakfast we will transfer by private van back to Florence and enjoy our final dinner together.

Depart at your leisure to your next destination.(B, -, -)

 

Note

Notes on the itinerary Day 1 is the day you should plan to arrive at the meeting point for the trip. This may require departing your hometown one or more days in advance. Although we do our best to adhere to the program, the itinerary may be subject to change for numerous reasons beyond our control, including group, weather, and terrain conditions.

Difficulty level: Moderately strenuous: Four to six hours of hiking every day with distances up to 20 km (12.5 miles) one day and elevation gains/losses up to 500 m (1600 ft) on various types of terrain (trails, dirt roads, some pavement). Good physical shape, prior training, and experience with hiking several days in a row are necessary.

Luggage: We will hike with a day pack and will not need to carry our luggage, which will be transported for us. Our luggage will nonetheless need to be light (no more than 12 kg/26 lbs per person, one piece max) and easy to move around. You may need to carry your luggage for short distances to reach the accommodations, at times climbing stairs or steep steps and on uneven terrain. We recommend you carry a small sturdy wheeled bag that you are able to lift up/down steps, as well as an overnight/day pack (minimum 25 liters or 1600 cubic inches) for day hikes, that can fit food, water, and personal items. Any extra luggage should be left at a luggage depot before departure.


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Itinerary characteristics


Medium length
12 km


Medium difference in height
1000 m


Average time
5 ore


Difficulty: ChallengingScala CAI EE

Requirements

Price and conditions

Starting from 3150

Supplemento singola 900 €

What is Included:

- Accommodation in 3-star hotels and pilgrim hostel with breakfast and tourist taxes included
- Dinners except on Day 4
- Picnic or light lunches (except on Days 1, 10)
- English-speaking guides during the whole tour
- Luggage transfer
- All transfer by public or private transportation unless otherwise specified
- Other activities as indicated
- Medical travel insurance

What is excluded:

- Transportation to/from trip start and end points (Firenze)
- Gratuities for trip guides
- Dinner on Day 4
- Lunch on Days 1, 11
- Items of a personal nature such as beverages other than water, laundry fees, internet fees
- Any other services not clearly mentioned in the Trip Itinerary and in the list of included items above
- Any unforeseen transportation costs (due for example to late arrival or early departure, inability to hike, etc.)

Minimum number of participants: 4. Maximum number: 10.

Clothing and backpack

 

 

Meeting point: place and time

Meeting point Firenze, Firenze FI, Italia, Firenze

 

Info and reservations

Passamontagna Viaggi

Contact details

Passamontagna Viaggi

Request information / availability




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