Day 1: Florence – Panzano (L, D)Meet your guide in central Florence in the morning and settle into an air-conditioned minivan with the rest of your small group. Then, drive into the countryside to collect your bike.
After around 15 minutes on the road, leave your minivan, and after a briefing, hop on your hybrid, 24-speed bike — a cross between a road bike and a mountain bike. Put on your helmet and set off behind your guide. You’ll ride around 20 miles (32 km) each day, mostly on secondary roads with little traffic and along gentle, hilly routes. The trip is suitable for moderate and active cyclists and the minivan will carry your luggage behind you.
Cross the undulating hills past olive groves, vineyards and romantic villas, and after an hour or so, arrive at a private wine estate in the northern Chianti region. Meet the winemaker host and tour the vineyard, cellar and olive mill as you hear how the wine and olive oils are made. Taste some olive oil and enjoy a light lunch of dishes such as bruschetta and pasta served with wine.
Continue on your bike towards Siena, passing through towns such as Greve. Break for coffee and, in Panzano, visit an artisanal butcher’s shop run by Dario Cecchini. Admire the shop and wares, and savor some of the cured meat offered to visitors. Ride another four miles (6 km) to your hotel in the nearby countryside. Enjoy an included dinner and the rest of the evening at your leisure.
Overnight: 3-star Villa Rosa near Panzano or similar
Day 2: Panzano - Siena - Florence (B, L)
Check out after breakfast and ride downhill before climbing to the honey-stone hill town of Radda. Stroll around its quaint lanes and then descend to Gaiole, home of Italy’s famous L’Eroica cycle race. After lunch at a restaurant on Gaiole’s main square, hit the road again, following an easy route to the pretty town of Pianella.
From here, ride in the minivan up to Siena, one of Tuscany’s most beautiful towns, or tackle the hill on your bike. On arrival, either return to Florence by minivan where your tour ends, or say goodbye here and stay on independently in Siena.