Day 1: Tavarnelle Val di Pesa

07:30–08:30 Arrive early in the morning in Tavarnelle Val di Pesa; drop bags and check in at hotel if room is ready (or arrange luggage storage)., 08:30–09:15 Drive from Tavarnelle Val di Pesa to San Casciano in Val di Pesa area for Antinori nel Chianti Classico (approx. 20–25 min, ~15 km)., 09:30–11:30 Antinori nel Chianti Classico: architect-led winery tour and tasting of Chianti Classico selections., 12:00–13:30 Lunch at Osteria di Passignano (San Casciano in Val di Pesa)., 13:30–14:05 Drive from San Casciano in Val di Pesa to Panzano in Chianti for afternoon tasting (approx. 30–35 min, ~20 km)., 14:15–15:45 Fontodi: estate tour and tasting focused on Sangiovese and flagship wines., 16:00–17:00 Vespa ride (self-guided) through the countryside around Panzano in Chianti; gentle loop before returning toward the hotel., 17:00–17:45 Drive back to Tavarnelle Val di Pesa (approx. 35–40 min, ~22 km)., 18:00–19:00 Rest at the hotel before dinner., 19:30–21:00 Dinner at the hotel restaurant (or a nearby local restaurant).

Via Benedetto Naldini, 61

🛏️Hotel

Tavarnelle in Val di Pesa

07:30–08:30 Arrive early in the morning in Tavarnelle Val di Pesa; drop bags and check in at hotel if room is ready (or arrange luggage storage).

Antinori nel Chianti Classico

08:30–09:15 Drive from Tavarnelle Val di Pesa to San Casciano in Val di Pesa area for Antinori nel Chianti Classico (approx. 20–25 min, ~15 km).

💡09:30–11:30 Antinori nel Chianti Classico: architect-led winery tour and tasting of Chianti Classico selections.

Osteria di Passignano

🍽️Meal

12:00–13:30 Lunch at Osteria di Passignano (San Casciano in Val di Pesa).

💡13:30–14:05 Drive from San Casciano in Val di Pesa to Panzano in Chianti for afternoon tasting (approx. 30–35 min, ~20 km).

Fontodi

14:15–15:45 Fontodi: estate tour and tasting focused on Sangiovese and flagship wines.

💡16:00–17:00 Vespa ride (self-guided) through the countryside around Panzano in Chianti; gentle loop before returning toward the hotel.

💡17:00–17:45 Drive back to Tavarnelle Val di Pesa (approx. 35–40 min, ~22 km).

💡18:00–19:00 Rest at the hotel before dinner.

💡19:30–21:00 Dinner at the hotel restaurant (or a nearby local restaurant).

Montefioralle

Visit Montefioralle

Day 2: Gaiole in Chianti

08:00–09:00 Breakfast at hotel and easy start., 09:00–09:50 Drive from Tavarnelle Val di Pesa to Gaiole in Chianti for morning tasting (approx. 45–50 min, ~35 km)., 10:00–12:00 Castello di Ama: art-filled borgo walk, cellar tour, and guided tasting., 12:15–13:30 Lunch at a local restaurant in Gaiole in Chianti; short stroll in the village., 13:30–13:55 Drive from Gaiole in Chianti to Castellina in Chianti (approx. 25–30 min, ~18 km)., 14:30–16:00 Castello di Fonterutoli: estate visit and tasting of Chianti Classico and Gran Selezione., 16:00–16:10 Short break for water and photos in Castellina in Chianti., 16:10–16:55 Drive back to Tavarnelle Val di Pesa (approx. 40–45 min, ~28 km)., 17:30–19:00 COMO Shambhala Retreat at Castello Del Nero: 60-minute signature massage and spa relaxation., 19:30–21:00 Dinner at the hotel or a nearby local restaurant in Tavarnelle Val di Pesa.

💡08:00–09:00 Breakfast at hotel and easy start.

💡09:00–09:50 Drive from Tavarnelle Val di Pesa to Gaiole in Chianti for morning tasting (approx. 45–50 min, ~35 km).

Castello di Ama

10:00–12:00 Castello di Ama: art-filled borgo walk, cellar tour, and guided tasting.

💡12:15–13:30 Lunch at a local restaurant in Gaiole in Chianti; short stroll in the village.

💡13:30–13:55 Drive from Gaiole in Chianti to Castellina in Chianti (approx. 25–30 min, ~18 km).

Castello di Fonterutoli

14:30–16:00 Castello di Fonterutoli: estate visit and tasting of Chianti Classico and Gran Selezione.

💡16:00–16:10 Short break for water and photos in Castellina in Chianti.

💡16:10–16:55 Drive back to Tavarnelle Val di Pesa (approx. 40–45 min, ~28 km).

COMO Shambhala Retreat at Castello Del Nero

17:30–19:00 COMO Shambhala Retreat at Castello Del Nero: 60-minute signature massage and spa relaxation.

💡19:30–21:00 Dinner at the hotel or a nearby local restaurant in Tavarnelle Val di Pesa.

Day 3: Montalcino

07:30–08:00 Light breakfast at hotel., 08:00–09:30 Drive from Tavarnelle Val di Pesa to Montalcino (approx. 1 h 30 min, ~70 km)., 10:00–11:30 Biondi-Santi Tenuta Greppo: historical estate tour and Brunello di Montalcino tasting., 12:00–13:30 Lunch at Osteria Le Potazzine in Montalcino., 13:45–14:00 Short transfer to Poggio Antico (approx. 10–15 min, ~6 km)., 14:00–15:15 Poggio Antico: guided tasting with focus on Brunello and Rosso di Montalcino., 15:15–15:35 Drive to Castiglion del Bosco Winery (approx. 20 min, ~12 km)., 15:45–17:00 Castiglion del Bosco Winery: estate visit and tasting flight., 17:15–18:45 Drive back to Tavarnelle Val di Pesa (approx. 1 h 30 min, ~70 km)., 19:00–20:00 Rest and freshen up at the hotel., 20:00–21:30 Farewell dinner at the hotel.

💡07:30–08:00 Light breakfast at hotel.

💡08:00–09:30 Drive from Tavarnelle Val di Pesa to Montalcino (approx. 1 h 30 min, ~70 km).