Starting point: Relais Borgo di Toiano, in Toiano, for two nights.
Spend your day relaxing by the hotel's outdoor pool, or follow an undulating circuit along winding roads through the silent woodland of La Montagnola, before returning via the 16th-century Villa Cetinale, near Sovicille. (23km)
Today, a short transfer brings you to the abbey of San Galgano, one of the most romantic sites in all of Tuscany. This ruined 13th-century Cistercian abbey is named after a local soldier who, after seeing a vision of St Michael commanding him to change his ways, thrust his sword into a rock as a symbol of his new life as a hermit. After admiring the abbey (and the accompanying chapel of Monte Siepi), you continue by bike to hill-top Massa Marittima where you stay overnight at the friendly Hotel Duca del Mare and take your pick from several atmospheric restaurants for dinner. (35km)
Massa Marittima was once the second city of the Sienese republic and is now the finest historic town of the Maremma. It boasts an exquisite cathedral and you will want to soak up the medieval splendour of Piazza Garibaldi in the lower Romanesque Old Town before setting off this morning. You ride via scenic Lake Accesa, set in a beautiful and tranquil landscape, perhaps choosing to extend the route by climbing up to Vetulonia to see the remains of a necropolis left by the mysterious Etruscans. Your destination is the stylish Montebelli Agriturismo near Caldana, where you spend two nights. (up to 50km)
Follow our circuit to Castiglione della Pescaia, an ancient fortified town on the coast with numerous seafood restaurants and beaches on which to relax. On your return, you can unwind in either of the hotel’s two pools or spa. (50km)
Leaving Caldana, you follow an enjoyable inland route to reach the medieval village of Roccastrada. Here you can potter around and have some welcome refreshment before spending your final night at nearby Hotel La Melosa. We include use of the Turkish bath, an ideal way to relax at journey’s end. (40km)
Add a city break in Siena or Pisa
Extend your holiday in magnificent Siena, staying two nights at the stylish 4-star Palazzo Ravizza, just a short walk from the famous Campo. We provide notes for a self-guided walking route so that you can discover the city’s Renaissance treasures. Alternatively, if flying via Pisa, add a stay in this historic city.