From Florence, the symbol of the Renaissance to the vistas of the Val d'Orcia, classified as a UNESCO World Heritage Site, this route will allow you to discover all the facets of Tuscany.
You'll spend portions of this trip hiking in Tuscany's most famous landscapes, including Chianti, Pienza and Montepulciano, and explore Tuscany's two most famous cities, Florence and Siena.
This week-long itinerary will have you witnessing centuries-old architecture, charming vineyards in the Tuscan countryside and medieval villages. From Florence, the symbol of the Renaissance to the vistas of the Val d'Orcia, classified as a UNESCO World Heritage Site, this route will allow you to discover all the facets of Tuscany.
You'll spend portions of this trip hiking in Tuscany's most famous landscapes, including Chianti, Pienza and Montepulciano, and explore Tuscany's two most famous cities, Florence and Siena.
This week-long itinerary will have you witnessing centuries-old architecture, charming vineyards in the Tuscan countryside and medieval villages.
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Itinerary
Day 1
Arrival in Florence
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Your adventure hiking in Tuscany begins with an overnight stay in Florence, the home town of Michelangelo. After you arrive and check in at your hotel, take some time to wander through Florence's historic city centre. Depending on your arrival time, you can visit the famous Duomo, view world-famous art at the Uffizi Gallery or stroll along the Arno River and explore the shops in the Ponte Vecchio.
Accommodation
Convitto Della Calza★3 star
Activities
Free Time in FlorenceOptional Activity
Cathedral of Santa Maria del FioreOptional Activity
Uffizi GalleryOptional Activity
Ponte VecchioOptional Activity
Destinations
Florence
Day 2
Hiking in Radda in Chianti
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This morning, you'll travel by bus or drive yourself to Radda in Chianti, where you will stay for two nights. The trip will take you about 1.5 hours. Then, it's time to hit the trail. From the village, the route crosses vineyards and olive groves on an old mule track through the Tuscan countryside. In the evening, enjoy a relaxing dinner in Radda in Chianti.
Accommodation
Hotel le Vigne★3 star
Activities
Hiking in Radda in Chianti
Transportations
Self-Driving from Florence to Radda in Chianti
Meals
Breakfast and dinner
Destinations
Florence
Radda in Chianti
Province of Siena
Day 3
Hike From Panzano to Radda in Chianti
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Today you'll travel by bus to Panzano, a 20-minute trip, and trek from there back to Radda in Chianti. This beautiful walk in the Tuscan countryside passes my ancient farmsteads, vineyards and forests. You'll pass through the village of Volpaia, built in the 11th century as a fortified village on the border between Florence and Siena.
Accommodation
Hotel le Vigne★3 star
Activities
Hiking in Panzano
Transportations
Bus from Radda in Chianti to Panzano
Meals
Breakfast
Destinations
Province of Siena
Panzano
Day 4
Sightseeing in Siena
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Today you'll travel from Radda in Chianti to Siena. If you are driving, consider making a detour to the medieval town of San Gimignano before heading to Siena. Spend the day visiting Siena's most interesting sights at your leisure. People-watch in the seashell-shaped Piazza Del Campo, explore Siena's Cathedral and view the art treasures in the cathedral's museum. After your day in Siena, travel to San Quirico d'Orcia, a journey that takes around an hour.
Accommodation
Hotel Palazzuolo★3 star
Activities
San GimignanoOptional Activity
Half-Day Tour to Siena and San Gimignano
Siena CathedralOptional Activity
Piazza del CampoOptional Activity
Transportations
Self-Driving from Radda in Chianti to Siena
Self-Driving from Siena to San Quirico d'Orcia
Meals
Breakfast
Destinations
Province of Siena
San Gimignano
Siena
San Quirico d'Orcia
Day 5
Trekking in Val d'Orcia
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From your hotel, you'll trek to the Val d'Orcia, a UNESCO World Heritage Site. After a short climb, you'll have a great view of the valley of oaks and vineyards with the citadel of Ripa d'Orcia and Monte Amiata, the highest point in southern Tuscany, in the background. You'll descend through the vineyards and, if you wish, cool off at Bagno Vignoni, a spa town with a Roman pool in its main square. As you head back to San Quirico, you'll go through the forest, sheltered from the heat.
Accommodation
Hotel Palazzuolo★3 star
Activities
Val d'Orcia
Meals
Breakfast
Destinations
San Quirico d'Orcia
Tuscany
Day 6
Hike to Pienza
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Today you'll hike 3 to 4 hours from your accommodation to Pienza, rebuilt in the 15th century in the humanist spirit of the Renaissance and listed as a UNESCO World Heritage Site. Spend some time in Piazza Pio II, Pienza's central square, which is surrounded by four important buildings: the Cathedral of Santa Maria Assunta, the Municipal Palace, the Borgia Palace, and the Palazzo Piccolomini.
Accommodation
Hotel Palazzuolo★3 star
Activities
Pienza
Meals
Breakfast
Destinations
San Quirico d'Orcia
Pienza
Day 7
Monticchiello, Montepulciano and Goodbye to Tuscany
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Today you'll take a 10-minute bus ride to Pienza and continue hiking in Tuscany to discover the fortified village of Monticchiello. Spend some time exploring this tiny medieval walled town. Next, you'll visit the village of Montepulciano, known for its wines and built on a peak of Monte Poliziano. After your hike, you'll return by bus to San Quirico d'Orcia, the endpoint of your trip.
Activities
Montepulciano
Transportations
Bus from San Quirico d'Orcia to Pienza
Bus from Montepulciano to San Quirico d'Orcia
Meals
Breakfast
Destinations
San Quirico d'Orcia
Montepulciano
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What’s included?
6 nights accommodation
5 activities
6 breakfasts and 1 dinner
Ground transportation
What’s not included?
Airport transfer
Alcohol beverages
Domestic flights
Entrance fees
Entry visas / airport departure tax
Gratuities
International flights
Laundry
Licensed English speaking guides
Personal expenses
Travel insurance
Trekking permits
Starting From
AU$ 1,879/ per traveller sharing
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Benefits of this trip
Italy in 7 days
3-star accommodation
24/7 in-destination support from your local designer
