Unique Experience Peregrine | Walking in Italy: Tuscany

Famous for its rolling, sun-drenched hills dotted with quaint villages and scored by manicured rows of vineyards, the Tuscan countryside remains an unspoiled vision of classical Italy. From captivating Florence, with its historic galleries and magnificent hilltop views, head out to the Val d’Orcia region and visit ancient villages waiting to be explored. Wander through crumbling castle remains in Monte Voltraio, get lost in the cobbled laneways of Volterra, and discover the hidden secrets of Siena. Taste local wines and experience an unforgettable night at a Tuscan farm.



  • Highlights

    • Discover charming villages such as Monticchiello, hidden to mass tourism by their location and tiny size
    • Enjoy a wine tasting in a Montepulciano wine cellar, the perfect end to a morning spent strolling in the Tuscan hills
    • Relax by supping a glass of Vernaccia on top of the city walls in the afternoon in San Gimignano, when most tourists visiting the town have disappeared. Vernaccia is a local grape varietal, produced in and around San Gimignano.
    • Uncover the secrets of the hilltop village of Volterra, famous for its magnificent sunsets and Etruscan ruins dating back more than 2,000 years. The Romans mined Volterra’s alabaster for sculpting.
    • Visit beautiful San Quirico and Pienza, both located in picture perfect Val d'Orcia, where you will check into your 'feature stay' hotel, a converted 15th century monastery.
  • What's Included


    7 Breakfasts, 1 Lunch, 1 Dinner


    Private vehicle , Local bus


    Comfortable hotel (5 nights), Feature stay in Val d'Orcia (2 nights)

    Included Activities

    • Arrival Transfer from Florence Airport
    • Florence Sightseeing Tour
    • Guided Hike in Val d'Orcia & Bagno Vignoni
    • Monte Voltraio Hike
    • Montepulciano Sightseeing Tour
    • Montichiello Country Hike
    • Pienza Sightseeing Walk & City Walls
    • Siena Sightseeing Tour
    • Via Francigena Hike to San Gimignano
    • Villa Palagione Visit
    • Visit to Abbazia di Sant'Antimo
    • Wine Tasting in Montepulciano
  • Pricing

      • Start Date
      • End Date
      • Price
      • Availability
      • Start Date:24 May 20
      • End Date:31 May 20
      • Price:$4,675
      • Availability:5 spaces
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      • Start Date:6 Sep 20
      • End Date:13 Sep 20
      • Price:$4,385
      • Availability:7+ Available
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      • Start Date:13 Sep 20
      • End Date:20 Sep 20
      • Price:$4,500
      • Availability:7+ Available
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      • Start Date:16 May 21
      • End Date:23 May 21
      • Price:$4,605
      • Availability:7+ Available
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      • Start Date:23 May 21
      • End Date:30 May 21
      • Price:$4,605
      • Availability:7+ Available
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      • Start Date:13 Jun 21
      • End Date:20 Jun 21
      • Price:$4,605
      • Availability:7+ Available
      • Enquire
      • Start Date:29 Aug 21
      • End Date:5 Sep 21
      • Price:$4,605
      • Availability:7+ Available
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      • Start Date:5 Sep 21
      • End Date:12 Sep 21
      • Price:$4,605
      • Availability:7+ Available
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      • Start Date:12 Sep 21
      • End Date:19 Sep 21
      • Price:$4,605
      • Availability:7+ Available
      • Enquire
      • Start Date:19 Sep 21
      • End Date:26 Sep 21
      • Price:$4,605
      • Availability:7+ Available
      • Enquire
    Please note: while prices are accurate at time of loading they are subject to change due to currency fluctuations and currency surcharges may apply. Please check price at time of booking
  • Itinerary

    Day - 1

    Location: Florence - Welcome to Florence, the cultural capital of Italy and the gem in Tuscany's crown. No activities are planned until tonight's group meeting, so you can arrive at any time. If arriving early, be sure to head out and see some of Italy's 'outdoor museum'. Perhaps pay a visit to Piazza della Signoria and marvel at the collection of famous statues there. In the evening, meet your trip leader and fellow travellers at a welcome meeting.


    Day - 2

    Location: Florence / Arezzo / Montepulciano - From your hotel walk into the heart of Florence with your tour leader and take some time to explore the outstanding works of art preserved over the centuries in this captivating city. Florence is considered the birthplace of Renaissance, as well as the cradle of the Italian language. You will stroll along its fascinating streets, and enjoy the essence of Italian history and culture. Pass along the Ponte Vecchio Bridge, visit Piazza della Signoria and gaze up at the landmark of Florence, the Duomo. At around midday you will drive to the town of Arezzo, the setting for ‘La Vita è Bella’. In Roman times it was the most important city of the Etruscan federation. You are free to wander around this interesting town and enjoy lunch at your leisure. In the late afternoon travel on to Montepulciano, one of Tuscany’s most attractive hill towns. Settle into your hotel before enjoying a group dinner together.


    Day - 3

    Location: Montichiello / Montepulciano - After breakfast, walk to the impressive Chiesa di San Biagio, a 16th-century church nestled at the edge of the Montepulciano village walls. Cross through the picturesque valley below, past vineyards, pastel-coloured villas and rolling hills, until reaching the village of Monticchiello. Here, enjoy lunch under the welcome shade of a grapevine canopy. Explore Montichiello's town walls and stroll through the charming town centre. Return to Montepulciano in the afternoon and enjoy a sightseeing tour of its labyrinthine maze of laneways and imposing defensive walls. The views from the walls across the Tuscan landscape are simply unforgettable.The afternoon will be at your leisure. Perhaps do some shopping in Montepulciano's classy boutiques. Later on in the afternoon take part in a wine tasting in a local cellar.


    Day - 4

    Location: Val d’Orcia / San Quirico / Pienza - This morning you will be transferred to the beautiful village of San Quirico, one of the lesser known jewels of Val d'Orcia. You may relax in its beautiful ornamental garden, or simply enjoy a coffee in one of the cafes lining the corso. You'll then embark on a beautiful walk through the distinctive landscapes of the Val d'Orcia, flat chalk plains interspersed by almost conical hills topped by fortified settlements. It is in this bucolic setting that you will reach the unique spa town of Bagno Vignoni. Here the main town 'square' is actually a picturesque ornamental pool built by the Medici family! Cool our heels in the many Etruscan water channels that surround the old watermills just outside of the town centre. This is a truly unique attraction in the Val d'Orcia but unknown to mass tourism. There are several options after the walk to Bagno Vignoni: Avid hikers can opt for a beautiful route all the way to Pienza, or alternatively you can choose to ride in our vehicle to the stunning chapel of Vitaleta. The short walk from here to Pienza, especially in the late afternoon, is one of the highlights of this trip. Arrive in Pienza and enjoy the views from Pienza's city walls that are quite simply spellbinding. Take time to pause and enjoy the captivating vistas afforded to you, the epitome of Tuscan landscapes rolling expansively before you - burnt orange villas, tightly wound hay bails, meandering country lanes and fields of barley. After arrival you will check into your feature stay hotel, a beautiful monastery converted into a hotel, right in the heart of the Utopian city of Pienza. Enjoy dinner on the premises of the monastery tonight.


    Day - 5

    Location: Val d’Orcia / Montalcino / Pienza - After a leisurely breakfast set off to the real highlight of this area, and arguably the most beautiful monastery of Tuscany: the beautiful Romanesque church of Sant'Antimo (Abbazia di Sant'Antimo) in a picture-perfect landscape. Here you’ll have the possibility to listen to Gregorian chanting. After an optional lunch depart for the charming village of Montalcino, one of the most stunning hilltop towns of the area. Montalcino, an authentic medieval village dominating the surrounding forests and vineyards, is in fact the capital of the world-famous Brunello wine. Visit the charming old town, stroll along the impressive medieval town walls – and perhaps do another wine tasting in the beautiful setting of the fortress of Montalcino. In the afternoon return to our base in beautiful Pienza. Sit in the garden, relax at the pool or just take a seat in the main ‘Corso’, sip on a local glass of Sangiovese and partake in another fine Italian tradition - the art of people-watching.


    Day - 6

    Location: Siena / San Gimignano / Volterra - After breakfast journey towards ancient Volterra. On your way pay a visit to Siena to discover the best of this most celebrated medieval city. Its heart, in every sense, is the famed ‘Piazza del Campo’, a grand fan-shaped piazza built on the site of the old Roman forum. Bordering the southern flank of the square is the 14th century Palazzo Pubblico, with some fine early Renaissance frescoes. Also of interest is the fine main church, the Duomo, a wonderful mixture of Gothic and Romanesque architecture, with a particularly splendid façade. After lunch your private bus will bring you to stunning San Gimignano. Those who wish can walk a beautiful stretch into town, along the Via Francigena, Italy’s most famous pilgrim road, to enter the city the way pilgrims have done for over a thousand years. Of course there is some time to stroll through this stunning medieval town, and perhaps climb one of its ‘skyscrapers’. Sip a glass of local Vernaccia wine in the most perfect setting you could dream of: sitting on the medieval town walls of San Gimignano overlooking the Tuscan hills. In the late afternoon we arrive in beautiful Volterra, full of Etruscan history, and famous for its alabaster, situated high on a plateau with sweeping views of the valleys below.


    Day - 7

    Location: Volterra - Explore the old town of Volterra and walk past the Etruscan walls and the Roman theatre. Head towards Monte Voltraio, a sandstone hill once dominated by a castle known as the Rocca di Monte Voltraio. At the foot of the hill stands the beautiful abandoned medieval building of the Casale Rocca. You’ll pass through pleasant landscape, meet with farmers still cultivating their land like in ancient times and pass the small 13th Century church of San Lorenzo. The goal of today’s walk is Villa Palagione. It is an ancient country residence built in 1598 by Geronimo Minucci, cupbearer of the Medici at the peak of the Florentine power and culture. In a setting that has seen four centuries of history, the villa still offers frescoed halls, a Gentility chapel and an Italian garden full of flowers and perfumes. Here you’ll stop for a short break, and then for those who want there is the possibility to climb up to the ruins of the castle on the top of Mt Voltraio, which offers superb views over the Tuscan countryside. Enjoy a picnic lunch at a picturesque spot from where you can enjoy a wonderful view of Volterra. In the afternoon make your way back to Volterra on foot. There is the possibility to relax in the gardens of Villa Palagione and dive into its panoramic swimming pool (and then travel back by bus) so pack your swimsuit! At the end of the day you can go and visit some of the last remaining alabaster craftsmen, who still practice this centuries old art, before joining the group for the last evening dinner in a local restaurant.


    Day - 8

    Location: Volterra / Florence - Your Tuscan adventure comes to an end with a morning transfer back to Florence. Arrival into Florence will be at around noon. We are happy to book additional accommodation for you in Volterra or Florence if you wish to stay longer (subject to availability).


    Walking in Italy: Tuscany
*Terms and Conditions
Offer subject to availability at time of booking. Prices are per person share twin based on best available tour price, inclusive of all discounts unless otherwise stated. Prices are subject to currency fluctuations and are based on cash or cheque. Tour deposit, amendment and cancellation conditions may apply. Travel agent service fees may apply. Special conditions apply - please ask for full details at time of enquiry.
HLO Ref# 14512
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