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Chianti and Val d’Orcia between trekking and e-bike

Chianti and Val d’Orcia between trekking and e-bike

Exploring Italy’s most enchanting landscapes.

5 days for an active vacation in a land of extraordinary landscapes, including excursions and visits to Arezzo, Siena, San Gimignano, Castelnuovo Berardenga, Montalcino and Montepulciano.

Italian Snapshots. Tuscany is a land known and adored all over the world, thanks in part to its stunning landscapes, which look more like a painting than a postcard. Avenues of cypresses, soft hills, sinuous vineyards, medieval villages, castles and fields of wheat the color of gold: dreamlike scenery that especially in the Chianti and Val d’Orcia areas are a real treat for the eyes. Landscapes not only to admire, but to experience to the full, crossing them on hikes that will make us feel at one with the spirit of the surrounding nature.

Along the Francigena. Siena, a proudly medieval city, enlivened by rivalries and pride of yesteryear, will be the base of our active vacation. We will tread in the footsteps of the pilgrims who set out along the ancient Via Francigena to reach Rome, retracing a stretch of this famous route from Gambassi Terme to San Gimignano. A true immersion in the unspoiled and suspended in time spirit of the Tuscan countryside, ending in one of its most fascinating and representative villages.

Promo and offers

Full Risk Insurance

Optional cancellation insurance

Allows you to be reimbursed in case of any* unforeseen event before departure. *Of those listed in the policy contract.

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fm 115€ up to 199€
FREE

Your holiday includes

TRANSPORTS

  • Grand Tour bus trip with pre-assigned seats

ACCOMODATION & MEALS

  • 4 overnight stays and breakfasts
  • 5 lunches including one packed lunch and one in a winery with wine tasting and 3 dinners (water included)
  • Wine tasting and typical products in San Gimignano

Tour manager

  • Accompanying person for the duration of the trip
  • Guided tours of Siena, San Gimignano, Arezzo
  • Excursion with certified hiking guide for trekking on the Via Francigena
  • E-bike excursion accompanied by certified bicycle tour guides
  • E-bike and helmet rental

Date and rates

  • Departure

    26.03.2025

    Bus tour
    fm 1.300 € per person
  • Departure

    09.04.2025

    Bus tour
    fm 1.350 € per person
  • Departure

    30.04.2025

    Bus tour
    fm 1.400 € per person
  • Departure

    21.05.2025

    Bus tour
    fm 1.350 € per person
  • Departure

    18.06.2025

    Bus tour
    fm 1.350 € per person
  • Departure

    03.09.2025

    Bus tour
    fm 1.350 € per person
  • Departure

    08.10.2025

    Bus tour
    fm 1.530 € per person
  • Departure

    12.11.2025

    Bus tour
    fm 1.350 € per person

Itinerary

Italian beauties and magical excursions
Tuscany’s landscapes are among the most beautiful in Italy and among the most dreamed of in the world. On this short tour we will be able to immerse ourselves in their idyllic beauty between walks in the footsteps of pilgrims, excursions on electric bikes and guided visits to the most characteristic villages.

DAY 1

Departure - Arezzo - Siena

We depart in the morning from our chosen location for Tuscany, stopping for lunch at a restaurant along the way. We arrive in Arezzo, an ancient city of Etruscan origin that has always maintained an important role in Tuscany over the centuries due to its location along the Via Cassia. We visit with the guide its historic center, with the splendid Piazza Grande, the Church of San Domenico and the Museo Diocesano with works by Vasari. We arrive in Siena in the evening for dinner.

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DAY 2

Via Francigena - San Gimignano

After breakfast we leave for Gambassi Terme, where we meet the hiking guides and begin our trekking activity along one of the most beautiful stretches of the Via Francigena. Along the way we stop for a light lunch with a travel basket. We arrive in San Gimignano, where we have some time to rest a bit. In the afternoon with the guide we admire the Duomo and the many towers that make the profile of this small fortified town unique. Following this we enjoy a tasting of local wines with samples of typical products. We return to the hotel in Siena for dinner.

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DAY 3

Siena - Chianti

We begin the day with a visit to Siena, the city of the Palio: we visit with the guide Piazza del Campo, with its distinctive shell shape, the exteriors of the Palazzo Comunale and the Torre del Mangia, and the marvelous Duomo. We then reach a winery nestled among the Chianti hills, where we have lunch and taste the famous local wine. In the afternoon we move on to Castelnuovo Berardenga, with its splendid medieval old town surrounded by the spectacular Crete Senesi, where we walk with our guide. Dinner is free, alternatively we have the option of joining an optional contrada dinner with an evening guide of Siena.

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DAY 4

Val d'Orcia

After breakfast we reach Montalcino for our bicycle touring activity among the Brunello lands. We meet the bike tour guides and then set off on a tour to discover the white roads and vineyards of this land. During the tour we stop for a light lunch at a typical local restaurant, and in the early afternoon we continue our exploration of the area by bike. At the end of the tour we return to the hotel and the rest of the day is at leisure to relax after cycling. In the evening dinner is included.

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DAY 5

Siena - Montepulciano - Rientro

.Before concluding our trip to Tuscany, we still have time for a chaperoned visit to Montepulciano, a charming medieval village enclosed by stone walls and perched some 600 meters above sea level. We then depart for the return journey, with lunch at a restaurant included along the way.

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Technical organization BOSCOLO TOURS SpA Via Uruguay 47, 35127 Padova – Rea PD – 423071 – P Iva 04845610288