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Fall in love with provincial Italy on this adventure through 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.
- Start
- Florence, Italy
- Finish
- Florence, Italy
- Destination
- Italy
- Style
- Peregrine
- Code
- PEUT
- Physical rating
- Trip rating
- 11 reviews
- Ages
- Min 15
- Group size
- Min 1, Max 12
Why you'll love this trip
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Enjoy a wine tasting in a Montepulciano wine cellar, the perfect end to a morning spent strolling in the Tuscan hills
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Discover charming villages such as Monticchiello, hidden to mass tourism by their location and tiny size
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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.
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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.
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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.
Is this trip right for you?
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You will need to be in good health and able to walk for 4-5 hours a day (5-12 km). The walks on this tour are mostly graded moderate and there are some up-and-down sections. The terrain varies from well-defined paths to rocky trails. The scenery is of course well worth the exertion!
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Summer temperatures can be extreme in Italy (over 40°C). It’s important to use sun protection, wear layers to combat the heat and drink plenty of water.
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As accommodation on this trip is twin-share, single travellers will share a room with another traveller of the same gender. If you’d prefer not to share, a single-room supplement is often available (at an additional charge). Many hotels in Europe don't have double beds, but rather two single beds that can be pushed together or apart.
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Itinerary
Accommodation
- Hotel Domus Florentiae or similar (1 night)
Included Activities
- Arrival Transfer from Florence Airport
Meals Included
There are no meals included on this day.Special Information
An arrival transfer from Florence Airport is included in the price of this trip, so please make sure you advise your agent of your arrival flight details. The group meeting usually takes place at 6pm but it is advisable you check the exact time and place at the hotel's reception. At this meeting the leader will give you a briefing on what lies ahead.Accommodation
- La Terrazza Di Montepulciano or similar (1 night)
Included Activities
- Florence Sightseeing Tour
Meals Included
- Breakfast
- Dinner
Special Information
Walking distance: 4-5 km; approximately 1,5 hoursAccommodation
- La Terrazza Di Montepulciano or similar (1 night)
Included Activities
- Wine Tasting in Montepulciano
- Montepulciano Sightseeing Tour
- Montichiello Country Hike
Meals Included
- Breakfast
- Lunch
Special Information
Walking distance: 10 km; approximately 4 hoursAccommodation
- Hotel Il Chiostro di Pienza (Feature stay) or similar (1 night)
Included Activities
- Pienza Sightseeing Walk & City Walls
- Guided Hike in Val d'Orcia & Bagno Vignoni
Meals Included
- Breakfast
- Dinner
Special Information
Walking distance: 10 km; approximately 3 hoursAccommodation
- Hotel Il Chiostro di Pienza (Feature stay) or similar (1 night)
Included Activities
- Visit to Abbazia di Sant'Antimo
Meals Included
- Breakfast
Special Information
Walking distance: 7 km; approximately 2 hoursAccommodation
- Hotel Etruria or similar (1 night)
Included Activities
- Siena Sightseeing Tour
- Via Francigena Hike to San Gimignano
Meals Included
- Breakfast
Special Information
Walking distance: 3-4 km; approximately 1 hourAccommodation
- Hotel Etruria or similar (1 night)
Included Activities
- Monte Voltraio Hike
- Villa Palagione Visit
Meals Included
- Breakfast
- Dinner
Special Information
Walking distance: 8-10 km; approximately 4 hoursMeals Included
- Breakfast
Special Information
If it is all ending too soon you can combine your trip with our 'Walking in Italy: The Amalfi Coast' trip, taking in the highlights of this beautiful stretch of Italian coastline, including a hike along the famous Path of the Gods and a boat ride to Capri Island. Alternatively you can head north and join our 'Walking in Italy: The Cinque Terre' trip, walking the scenic trails of the renowned Cinque Terre region and the Portofino Peninsula. Most departure dates coincide to create the perfect combination and a transfer between trips can readily be booked. Please speak to your booking agent for more details.Meals
7 breakfasts, 1 lunch, 3 dinnersTransport
Private vehicle, Local busAccommodation
Comfortable hotel (5 nights), Feature stay in Val d'Orcia (2 nights)Included Activities
- Arrival Transfer from Florence Airport
- Florence Sightseeing Tour
- Wine Tasting in Montepulciano
- Montepulciano Sightseeing Tour
- Montichiello Country Hike
- Pienza Sightseeing Walk & City Walls
- Guided Hike in Val d'Orcia & Bagno Vignoni
- Visit to Abbazia di Sant'Antimo
- Siena Sightseeing Tour
- Via Francigena Hike to San Gimignano
- Monte Voltraio Hike
- Villa Palagione Visit
Dates & availability
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Important notes
LEVEL OF FITNESS
You'll need to be in good health and able to walk for a few hours, with some up-and-down sections, and on varied terrain, from well-defined paths to rocky trails. You will be walking on well defined paths for 4-5 hours (5-12 km) per day.
ARRIVAL TRANSFER
An arrival transfer from Florence Airport to the start point hotel is included in the price of the trip. Please advise your travel agent of your flight times at the time of booking.
SINGLE SUPPLEMENT
A single supplement is bookable on this trip, subject to availability at the time of booking. Please note that due to the small properties we use in Europe there is only a limited amount of single supplements available per trip departure. If you would like to book a single supplement and enquire about availability please speak to your booking agent.

Essential trip information
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