Total tour distance: 80 miles
Daily tour distance: 27 miles
Difficulty: 50 / 100
Tuscany is an iconic name, symbolizing the good life - a vacation to enjoy all that is good: food, sun, lifestyle, wine, amusement, and relaxation. The culture of the region adds charm, and you can indulge yourself in this opulent way because you will cycle the famous undulating countryside. This Tuscany cycling tour starts in Pienza, and makes its way to Florence, where along the way you will visit the villages that have made Tuscany famous. You can enjoy very charming 3/4 star accommodations and devour your choice of divine Mediterranean cuisine. The hilly terrain makes this tour somewhat challenging!
Day 1 | Arrival Day FLORENCE, Explore the city on foot.
Arrival in Florence. Time at leisure to explore the Palazzi Churches and museums that contain more art than any other city in the world. Bike set up and orientation either this afternoon or tomorrow morning. Optional guided walk of the city: our visit will take you to explore places off the beaten path known only by the Fiorentini! Dinner on your own.
Day 2 | FLORENCE to GREVE IN CHIANTI (40-70km)
Today’s ride heads from the Arno Valley, entering in the rolling hills of the Florentine Chianti Classico, from Ponte a Ema, once area of the legendary cyclist Gino Bartali, to Grassina a lovely little village with a delightful “trattoria” and then to the unparalleled vineyards and the olive groves of Chianti. Our biking finishes up on our arrival into the beautiful square of Greve in Chianti. Ride details: The level is moderate-difficult approx 40 km (100% asphalt), quite rolling with 2 climbs. A longer route (70 km) is available. Highlight: the picture-postcard hills covered by oak woods and vineyards.
We can extend this trip by 1 night and do a loop tour tomorrow around Chianti and return to the same hotel. Contact us for a quote and details.
Day 3 l GREVE IN CHIANTI to SAN GIMIGNANO (48km)
Undulating ride in the Chianti hills passing through small picturesque villages like Montefioralle and San Donato in Poggio with breathtaking vistas. A challenging ride with some steep sections, but definitely worth the effort for the beautiful Tuscan scenery and the final destination – the ancient town of San Gimignano. This UNESCO site is known as Medieval Manhattan for its 13 imposing towers dating back to the 12th century and is a delight to explore. Ride details: The level is moderate-difficult approx 48 km. Highlight: a stroll in the narrow alleys of San Gimignano away from the Corso, contemplating the sunset with a glass of Vernaccia wine.
Day 4 l SAN GIMIGNANO to SIENA (40km)
From San Gimignano we will move south, to the lesser known town of Colle di Val d’Elsa, famous for its crystal glassware and its very charming Medieval historic center. The old town sits atop a long ridge that descends down to the valley where meets Colle Bassa the lower part of the town, founded in the Renaissance period. Next we come to the tiny citadel of Monteriggioni. The walls of the town are largely still intact and it’s well worth a short visit to evoke the Middle Ages when the whole of the Siena province was at war against Florence. The rest of the ride is coasting the Montagnola Senese, a forested limestone hill range west of Siena, before arriving in the city itself, home to the famous Palio horse race. Ride details: The level is moderate approx 40 km. Highlight: Arriving in Siena and visiting the Campo, the Cathedral and the historic center bursting with life.
Day 5 l Departure Day
Departure after breakfast, at your leisure. If you want to go back to Florence, we can arrange transportation and hotels. Trains, car rentals can be arranged as well additional stays throughout Italy.
- Deluxe lodging 3 and 4 stars - double room with private bath
- Buffet breakfast daily
- All luggage transfers from hotel to hotel
- Local emergency support throughout your tour during daylight riding hours
- Arrival orientation and bike set up
- Route maps, route cue sheets with suggestions for visitation and site information
- All pre and post travel planning services
- A package of pre-travel documents sent electronically to help you prepare for your trip.
Accommodations: Stay in deluxe 3 & 4-star hotels in convenient locations. All lodging includes private bathroom and a variety of other amenities. Hotels included:
- Hotel Guelfo Bianco *** Florence
- Hotel Castello di Vicchiomaggio*** Greve in Chianti
- Relais Santa Chiara **** - San Gimignano
- Palazzo Ravizza **** Siena