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Tuscany – Hiking Experience in the Chianti Region - 8 Days

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From 1209 € per person

Florence – Colle Val d’Elsa – San Gimignano – Siena – Montalcino

Day 1: Arrive in Chianti
Arrival transfer from the airport to hotel. Rest of the day at leisure.
Hotel in the Chianti area

Day 2: The secrets of Chianti
Through the vineyards of Chianti, our trail will cross the Pesa River and takes us past the Romanic church of Santa Maria Novella and further to Volpaia, an impressive medieval village. Time seems to stand still here, the fort was built in the 11th century and its rustic residential houses are treasured like ancient jewels. After an invigorating break at Paola’s cosy Bar Ucci we will hike downhill through vineyards overlooking Radda until we arrive at the coach, which will take us to the old part of town.
Hotel in Chianti area
Total duration: 3,5 hours
Height difference: ca.1.300 feet
Level of difficulty: intermediate

Day 3: Urban trekking in Florence
Florence’s cathedral dominates the skyline and together with the Bell Tower and the Baptistery forms one of the most magnificent art masterpieces in the world. The austerity and beauty of this city, and the pride and determination of the Florentine artists are displayed in a unique way in the Palazzo Vecchio. With a local English-speaking guide we discover the major sites before we will sample the typical Tuscan sweet wine, Vin Santo, in a local wine bar.
Hotel in the Chianti area

Day 4: Greetings to the Etruscans - Montefioralle and San Cresci
The triangular square of the pretty wine-town of Greve in Chianti will be the starting-point of our hike. A 30-minute walk will take us past the wonderful hills covered in vineyards to the medieval village of Borgo Monterfioralle, which was the first Etruscan settlement in the Chianti area and a fortified castle. The Sieni family runs a small but much appreciated winery in this medieval village, where we will enjoy a glass of Chianti and a small snack. We then continue to the Romanic church of San Cresci, built in 963, and along a graveled path we will reach Zano and eventually get back to Greve.
Hotel in the Chianti area
Total duration: 3 hours
Height difference: ca. 2.000 feet
Level of difficulty: easy

Day 5: The Franks Road in Colle Val d’Elsa and San Gimignano
From Piazza Arnolfo di Cambio in Colle Val D’Elsa we will hike over graveled roads, farm roads and gentle hills. The old Franks Road traveled by the Archbishop of Canterbury on his pilgrimage to Rome in 990 takes us to San Gimignano, famous for its Vernaccia wine. We will take a break to taste some local wine and Tuscan specialties before we reach San Gimignano, the “Medieval Manhattan”.
Hotel in the Chianti area

Total duration: 5 hours
Height difference: ca.1.300 feet
Level of difficulty: intermediate

Day 6: Urban trekking in Siena
In Siena a guided tour of the historical center awaits you. The highlight is the Piazza del Campo, the seashell-shaped square on which the famous horse-race, the Palio, takes place each year. Another site not to be missed is the imposing Cathedral. You can enjoy walking up and down the narrow streets of Siena discovering something new around every corner.
Hotel in the Chianti area

Day 7: The Abbey of Sant’Antimo and Montalcino
This morning we board our coach bound for the Abbey of Sant’Antimo, one of the most beautiful Romanesque churches of Tuscany, which is set in a lovely hilly landscape surrounded by cypresses and olive trees. We then follow the road that takes us through woods, olive groves and gentle hills admiring the pretty views of the D’Orcia Valley and Mount Amiata. After a short break, we will travel to Montalcino by coach, where we will taste one of one of the most appreciated wines in the world, the Brunello.
Hotel in Chianti area

Total duration: 3 hours
Height difference: ca.850 feet
Level of difficulty: easy

Day 8: Chianti area
Departure transfer from the hotel to the Airport. End of services.

Transportation and Hotels

  • Transfer from Florence Airport to the hotel in the Chianti area
  • Transfer from the hotel in the Chianti area to Florence Airport
  • Transport by deluxe AC motor-coach as per the itinerary
  • 7 nights at 4* Hotel Villa San Lucchese in Poggibonsi (or similar)

Food and Drinks

  • 7 buffet breakfasts
  • 7 3-course dinner at the hotel
  • Typical meal at Paola’s in Volpaia
  • Wine-tasting of Vin Santo (day 3)
  • Wine-tasting with snack in San Cresci (day 4)
  • Vernaccia wine-tasting with snack in San Gimignano (day 5)
  • Wine tasting of Brunello di Montalcino (day 7)

Experiences and Services

  • English-speaking trekking-guide for excursion from Radda in Chianti to Volpaia (day 2)
  • 3-hour city tour of Florence with English speaking guide (day 3)
  • English-speaking trekking-guide for excursion to Montefioralle and San Cresci (day 4)
  • English-speaking trekking-guide for excursion to San Gimigano and Colle Val D’Elsa (day 5)
  • 3-hour tour in Siena with English speaking guide (day 6)
  • English speaking trekking-guide for excursion to Sant’Antimo and Montalcino (day 7)
  • 1 pair of ACTIVO-hiking poles per person
  • Porterage on arrival and departure at each hotel
  • Headphones throughout the tour

The tour does not include:

  • Tips, everything not listed under “our package includes”
  • City taxes

Please note the city taxes are not included and have to be paid by the guest directly to the hotel at the time of check in. The amount of the taxes depends on the category of the hotel and length of stay. Please check our web-site for additional information about the rates and cities where the taxes are applied.


4* Hotel

  • per person in a double room (10 to 14 passengers) from
    1544 €
  • per person in a double room (15 to 19 passengers) from
    1329 €
  • per person in a double room (20 to 25 passengers) from
    1209 €

Mind your option

  • Single room supplement from
    219 €

4* Hotel


Accomodation in 4* Hotel

Hotel Villa San Lucchese 4* - Poggibonsi

The prices are per person sharing a double/twin room
Tours are on request and rates are subject to the availability at the time of booking. If travel dates occur during the trade-show season, Bank Holidays, or particular events a supplement will apply.
Prices are subject to change based on the 2020 trade-show calendar.


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