There are many options for bike trips in Toscana. The distance per day suggested below is relatively short (28 to 36 km), so the round trip may be more suitable for newcomers to Toscana than for very experienced cyclists.
Accomodations in Firenze are easy to find. Bicycles can for example be hired from Florence by Bike. Please remember travel insurance, use a helmet, lock your bicycles and keep your luggage safe.
Day 1. Firenze to Panzano in Chianti (36 km, map link)
Start: Ponte Amerigo Vespucci on south side of river Arno. Go west along Arno, take first road to the left (Piazza Versale / Viale Ludovico Aristo). Go left on Viale Fransesco Petrarca to Piazzale de Porto Romano, continue south to the end of Viale del Poggio Imperiale. Turn left (southwest) along Via di S. Felice a Ema ending in a round-about. Turn left along road SP70, taking you south to Impruneta, with a nice view along the road. In Impruneta, take road SP69 south to the town centre, where a lunch café can be found.
From Impruneta, the suggested route continues south along Via del Ferrone to road SP3 (Via Chiantiagna per Ferrone) which is followed to Frantoio del Grevepesa. There turn right, going uphill for many kilometres on road SP92 (Via Gabbiano), continuing on road SP118 which is followed to Panzano in Chianti, where many accomodations and restaurants are found. Relais Fattoria Valle can be recommended for dinner and overnight stay.
Staying more than one night in Panzano may be a good idea, for walking or for a bike trip to Greve in Chianti and Montefioralle.
Day 2. Panzano in Chianti to Monteriggioni (28 km, map link)
From Panzano, bike south along road SR222 (Via Chiantigiana) downhill to 270 m and then uphill with a nice view to 570 m at Castellina in Chianti, where a lunch café can be found.
South of Castellina, the suggested route turns right (southwest) from SP222 to SP51, going downhill and ending on road SR2 (Via Cassia) at Castellina Scalo. Go south along SR2 to La Colonna, and turn left from SR2 steeply uphill along Via 1 Maggio to Monteriggioni.
Monteriggioni is a well preserved fortified medival town, which was an etruscan village in pre-roman time. Hotel Monteriggioni can be recommended for overnight stay.
Day 3. Monteriggioni to San Gimignano (29 km, map link)
Take the western path down from Monteriggioni to Via Cassia, and take road SP5 towards west out of the rondabout at La Colonna towards Colle d’Elsa. The suggested route takes a small detour near Parco Fluviale dell’ Alta val d’Elsa, turning left from SP5 to SP541 and right in next roundabout, continuing north along river Elsa on Strada dei Poveri from where a short visit to the river park may be possible.
Back on SP5, the suggested route goes over the bridge to Colle d’Elsa and along Via di Spugna and Via Romano Bienchi to Pista ciclabile Colle-Poggibonsi, which goes along a former railway line.
A stop may be made to look at Colle d’Elsa before continuing to Poggibonsi. The bike path ends on road SP1 (Via San Gimignano) which is followed to San Gimignano, where several accomodations and restaurants are found. Hotel Leon Blanco can be recommended for overnight stay.
San Gimignano is a very nice and well preserved medival city. It is a good starting point for cycling daytrips in the present part of Toscana, so staying more than one night can be recommended.
Day 4. San Gimignano to San Casciano in Val di Pesa (35 km, link)
Take the northern exit through the city wall of San Gimignano, go north on Via Dante, and turn left (north) along road SP127 through a nice rural landscape. After 3.5 km, turn left along Strada di San Benedetto, continuing north named SP95 towards Certaldo.
Into Certaldo, continue from SP95 to SP1, and turn southeast along Via Caduti del Lavoro continuing northeast on Via Aldo Moro and Via Romana to SP79 (Via Fiorentina). Go uphill along SP79 through Fiano and Lucardo, where a lunch café may be found along the road.
Continue north to Quercione, where the suggested route turns right (northest) along road SP93 through San Pancrazio and Ponte Rotto towards San Casciano in Val di Pesa, where many accomodations and restaurants are found. Villa I Barronci Resort & Spa can be recommended for dinner and overnight stay.
Staying more than one night in San Casciano may give an opportunity for local bike trips in the Val di Pesa area.
Day 5. San Casciano in Val di Pesa to Firenze (28 km, map link)
The suggested route goes through the centre of San Casciano and southeast along road SP92 (Via Grevigiana), turning left (north) along Via di Luiano just before Mercantale in Val di Pesa. Via di Luiano ends at road SP3, which is followed north to the first crossing, where the route turns right (north) along Via di Capello uphill to Impruneta.
Between Impruneta and Firenze, the suggested route is the same as for Day 1, with a nice view along road S70 going downhill to Firenze.
