Long: At Pontassieve you can decide to take a number of challenging but beautiful Apennine climbs. There is the Passo della Consuma or the stunning Vallombrosa and Monte Secchieta road from Sant’Ellero. Otherwise going north, turn off either at Contea for the Passo Croce ai Mori or continue towards Passo del Muraglione after Dicomano.
Chianti Classico
Medium: Firenze to Greve-in-Chianti is a relatively easy ride. Heading south, take the Via Senese from Porta Romana, then find your way onto Via Cassia at Galluzzo. At Falciani, turn onto the Via Chiantigiana which takes you all the way to Passo dei Pecorai where you can either keep it flat or have a bit of a climb off to the left. Either way, you’ll end up on the run into Greve, where you can turn into the market square for coffee and pastry or something more substantial.
Long: At Greve, you can try a longish but lovely climb to Passo del Sugame and return via the equally lovely road through Panca which spits you out at Strada In Chianti and back towards Florence. Alternatively, climb to Panzano and return along the “Testalepre” towards Mercatale in Val di Pesa and next do the steady climb into San Casciano in Val di Pesa before a wonderful return back into town via Chiesanuova and the Via Volterrana (be very careful on the technical hairpin descent into Galluzzo).
Medium: The recently inaugurated UCI World Championship course offers a bit of a challenge, climbing up to Fiesole. If continuing on to Quattro Strade, you can head down the sweeping Via Faetina towards the city and take the sharp right-hander up the dreaded Via Salviati wall-climb like the pros in 2013. Otherwise, either make your way to Pratolino by way of the Via della Casa al Vento and Via della Lupaia and descend back into Florence down the Via Bolognese, or turn off for a rollercoaster ride up and down Monte Morello where you can hit some serious speeds with less traffic.
Long: at Quattro Strade, take the Via Faetina into the Mugello valley and try an Apennine mountain pass or two such as Passo della Futa near Barberino, Passo del Giogo above Scarperia or Passo della Colla after Borgo San Lorenzo. Look out for motorcyclists out on their Ducatis who often use the roads at breakneck speeds and don’t forget to save some energy for the slog back home!
Medium: You can reach a great pasticceria, Vezzosi in Montelupo Fiorentino, after a nice ride winding along the Arno. From there you can loop back home through the Val di Pesa, climbing the Via Volterrana at Cerbaia and head home.
Long: instead of Montelupo, take Via Cavalcanti out of Signa and work your way up to Carmignano from Comeana, eventually reaching the peak at Pinone for an alternative bar pit-stop. You can head back home taking the twisty Via Castra or, for the more adventurous, follow signs for Vinci (birthplace of Leonardo), where you can start the spectacularly fun and forgiving climb to the cyclists’ bar at San Baronto where you may have a close encounter with local pro cyclists such as Mark Cavendish or the Nibali brothers!
Medium: The Via Aretina / Aretina Nuova is a rolling road that follows the Arno upstream to Pontessieve where you can turn at the Sieve river until Dicomano. Once there, cross over to the west bank and enjoy a quieter, undulating pedal all the way to the Via Faentina near Borgo San Lorenzo where you can turn off and climb towards Florence through Faltona, Polcanto and Mulinaccio. At Vetta Le Croci the road starts going downhill, so head straight and let gravity do most of the work back into town.