Tuscany: Guided Walking Holiday
Rolling hills, wine villages and cypress trees in Chianti.
Day 1: Flight to Florence or Pisa
Make your own way to Florence Airport; transfer to the hotel in Greve in Chianti. Budget flight booking through us on request. In the evening, welcome and introduction to the programme by the tour leader.
Day 2: Walk from Quattro Strade to Greve
By hotel bus to the start point at la Quattro Strade; walk along a lovely hillside path to the ruined church of San Martino in Valle, from there to Castello Verrazano; climb up to Querciolina, then descend to Greve in Chianti and the hotel (270 m of ascent, 13 km, 4½ hours).
Day 3: Walk to San Gimignano
San Gimignano rises on a hill in a magnificent setting above the beautiful Tuscan hills and, with its many towers, is one of the jewels of tourism in Tuscany. First by hotel bus to near Poggibonsi, then walk along panoramic ridge paths and through vineyards up to the town of towers (approx. 330 m of ascent, 12 km, 3½ hours), return by hotel bus.
Day 4: Florence
By public bus to Florence, the capital of Tuscany. Guided city tour of this city on the Arno, so rich in art and culture: the Town Hall, Palazzo Pitti, Ponte Vecchio, the Cathedral of Santa Maria del Fiore and more. In the afternoon, plenty of time for your own explorations or to visit one of the many museums. Return by public bus to Greve.
Day 5: High-level walk to Castello Volpaia
By hotel bus to the start on the Passo del Sugame at 530 m. From there, walk to Pian della Canonica and continue gently uphill, with wide views across the countryside, to Monte San Michele at 890 m, the highest point of the walk; then through a nature reserve and finally down to Castello di Volpaia, with a stop at a small, cosy trattoria (360 m of ascent, 12 km, 4 hours), then by hotel bus back to Greve in Chianti.
Day 6: Siena
In the morning by hotel bus to Siena, a city that has preserved its medieval appearance. Guided city tour through narrow lanes to small, dreamy squares; to the Duomo Santa Maria, an overwhelming structure of white marble and black-green serpentine, Siena’s colours; to the shell-shaped Piazza del Campo, paved with red bricks, with the Fonte Gaia, lined with cafés, restaurants and palaces; and the Palazzo Pubblico, dominated by the Town Hall tower, climbed via 412 steps. On the square the well-known horse race of the contrade takes place annually, the Palio. After the tour, plenty of free time; in the late afternoon return by hotel bus to Greve in Chianti.
Day 7: Walk to the mountain village of Lamole and wine tasting
From the hotel in Greve, climb to Monto Calvario, below the ridge passing wineries with vineyards and glorious far-reaching views; after a short break continue through vineyards and woodland to the small mountain village of Lamole, where we stop at a typically Tuscan trattoria; wine tasting with cheese and ham; afterwards back to the hotel by bus (approx. 440 m of ascent, 12 km, 4 hours).
Day 8: Departure
After breakfast, bus transfer to Florence Airport, then flight back to Germany.
Centre-based walking week in Chianti with hotel in Greve (family-run hotel with garden pool). Arrival in Florence or Pisa and transfer to Greve. Guided walks to San Martino in Valle and Castello Verrazzano, to San Gimignano, over Monte San Michele to Castello di Volpaia, and to Lamole with a wine tasting. Guided city tours in Florence and Siena, time at leisure. Bus transfers as per programme. Return flight from Florence. Dinner not included.
Public transport, museums and tourist tax payable locally. Flight not included. On request, we can arrange low-cost flights.
Individual hiking tours
Individual hiking tours can be undertaken at the given times without a hiking guide.
Guided hiking tours
Guided hiking tours take place on fixed dates in a group with an experienced hiking guide.
Single-hotel tours
On our single-hotel tours you start a hike every day from one fixed hotel.
Tuscany: Guided Walking Holiday
Rolling hills, wine villages and cypress trees in Chianti.
Tour "Tuscany: Guided Walking Holiday"
Trip
8-day Tuscany walking holiday to Greve in Chianti, 24.04.2027 - 01.05.2027Room
DoubleSingle
Price p. p.
1.945,00 €2.340,00 €
- Difficulty level: moderate
- Walking style: guided, no hotel changes
- Distance: 49 km / 1400 metres of ascent


