As you are starting from the hilltop town of Volterra, you will start by enjoying a nice section of downhill to get you in the swing of things. You will head down the Era Valley with spectacular views of the surrounding Tuscan countryside. Having absorbed the views it will then be time to climb gently out of the valley through the pretty hamlet of Castagno where you can enjoy your first coffee break. Your route then continues onto Gambassi Terme, a spa town with cobbled streets, a 12th Century church and lovely shaded gardens. If you are here for lunch then you could relax in one of the many trattorie before climbing back on the bikes and picking up the famous Via Francigena which will take you to the hamlet of Pancole.
Today is free to please yourself, so if this means enjoying the lovely hotel pool, then you can do just that. The hotel serves fantastic lunches on the terrace so you can really relax if you want to. There us also a small enoteca where you can sample local cheeses, olive oils and wines. If you want to explore further afield you can cycle or take a taxi to Certaldo, the birthplace of Giovanni Boccaccio, an important Renaissance Humanist, author and poet. In Certaldo you can visit the house of Boccaccio. It is also worth taking the funicular to the mediaeval town centre for spectacular views across the Val d'Elsa.
Today's route explores the panoramic wine country between Pancole and Colle di Val d'Elsa. First, you will follow the official, mainly off-road, Chianti Wine Route. There a plenty of wine tasting opportunities here. You then head onto the old town of Poggibonsi, which offers the perfect lunch stop. Here you can visit the ruins of the unfinished 15th Century fortress. As you climb out of the town you will pass the Basilica di San Lucchese, a 14th Century convent resplendent with original frescoes and offering fabulous views. Your final stretch is then through countryside adorned with poppies, vines and olives, bringing you to Colle di Val d'Elsa.
You have so much choice for your free day today. You can stay and explore the mediaeval old town of Colle di Val d'Els, which dates back to Etruscan times. Alternatively, you can venture further afield to Siena or to Florence (30min or 60min by bus respectively). There is also the option to stay and enjoy the hotel pool and it's lovely gardens.
It is flat, easy pedaling this morning as you head south via the high old town of Colle di Val d'Elsa and onto Casole d'Elsa, a beautiful village characterised by ancient vermilion-hued buildings and blessed with stunning balcony views from its hilltop position. It is worth taking the time to explore the 12th Century church with it's frescoes by Gano da Siena. You could then break for lunch in the lovely piazza before exploring the impressive fortress. On leaving Casole d'Elsa you wind through wonderfully scenic countryside, with San Gimignano and its mediaeval towers giving a formidable backdrop as you cycle onto San Donato.
You are just 5km from San Gimignano today so you can easily cycle or take the hotel's shuttle bus, even walk if you fancy slowly taking in the views. The mediaeval town has a spectacular and well photographed skyline, with it's many towers which you can explore on arrival. It is a wonderful place to wander around and take a lazy lunch before heading back to the hotel to enjoy the pool and extensive hotel gardens. Dinner is taken in the courtyard, bedecked with flowers, which makes for a very romantic setting after a day spent in a fairytale town.
You will start with an exhilarating downhill whiz to San Gimignano before a gentle climb up through classic Tuscan landscapes of vines, olive groves and fields ablaze with sunflowers and into the pretty Era Valley. The views leading you back to the cobbled streets of Volterra are spectacular and will reward your efforts. You can finish the day with a refreshing dip in the pool before dinner.