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Self-Guided
San Gimignano Bike Tour
This cycling holiday highlights the splendors of central Tuscany. On this tour you stay in three of Tuscany's most beautiful hill towns, Certaldo, San Gimignano, and Volterra. Visit a country villa, tour their winery and sample their full-bodied Chianti Classico wines. Ride the funicular up to the old town of Certaldo. Cycle to San Gimignano and be enchanted by the town's 14 stone towers. You spend two nights in San Gimignano leaving plenty of time to explore. You can visit an abandoned castle or cycle to a medieval town famous for its crystal glassware production. Pedal through olive groves and vineyards to Volterra, an Etruscan fortress surrounded by lush countryside. Volterra hasn't been transformed by tourism and is perhaps Tuscany's best kept secret. The town proudly features a Roman amphitheater and the world's best Etruscan museum.
​Highlights
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Winery and olive mill tour with tastings
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Stone towers of San Gimignano
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Roman theater of Volterra
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Beautiful Tuscan scenery and peaceful country roads
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The town of Volterra
Price
US$ 1,000 per person, double occupancy
Dates
Any date, Mar 1 to Dec 1
Single Supplement
+ US$ 200 for single room occupancy
Length
5 Days, 4 Nights
Meet / Finish
Florence / Volterr
Route Rating
Moderate: 9-21 miles (15-33 km) per day over hilly terrain. Extra miles available.
Bikes and Gear >
Terms and Conditions >
Day 4 and 5: Volterra
We have saved the best cycling for last. Dense woodlands give way to peaceful rolling hills as the countryside opens up before you. Volterra is one of Tuscany's most beautiful hill towns, and yet remains well off the beaten tourist trail. Your hotel is in the historic center close to all the sites. Explore Volterra's Roman theater and marvel at its Etruscan gate. Frequent busses make for an easy departure from Volterra on day five.
Day 1: Certaldo
We meet in the center of Florence and shuttle by van to our bike storage in the Chianti countryside. You ride to a 16th Century winery and enjoy a private guided tour. Day one includes a wine and oil tasting over lunch. After lunch pedal to the perfectly preserved medieval village of Certaldo. Your 4-star hotel features a pool and huge garden.
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Day 2 and 3: San Gimignano
Cycle past a castle and vineyards on your way to San Gimignano. Along the way enjoy beautiful views of San Gimignano's stone towers. After lunch climb a tower, shop, or just savor a cappuccino in a pretty piazza. On day three you have the option of hiking to an abandoned castle, pedaling to a winery, or cycling to Colle di Val d'Elsa, famous for its crystal glassware. While in San Gimignano be sure to try the local Vernaccia wine, a tangy crisp Tuscan white. If gelato is more your speed you can't go wrong at the Gelateria Dondoli, described by many as one of the best gelaterias in Tuscany.
Daily Itinerary
Daily Distance
Lodging
Hotel Certaldo
Certaldo (1 night)
The four-star Hotel Certaldo is located in a renovated watermill on the Elsa river. The hotel has air-conditioning, a pool, a great breakfast, and super friendly staff.
hotel website >
Hotel Leon Bianco
San Gimignano (2 nights)
You stay in an 11th Century palace on San Gimignano's most beautiful piazza. The building has been carefully restored preserving its special character.
hotel website >
Hotel La Locanda
Volterra (1 night)
This four-star hotel is located in a converted nunnery in the historic center of Volterra. The hotel features air-conditioning, free WIFI, and a small garden.
hotel website >
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All lodging (three star hotels)
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All breakfasts
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One lunch
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Winery visit and wine tasting
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Luggage transfers from hotel to hotel
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Private van transfer from Florence on Day 1
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4 beautiful rides (extra miles available)
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Use of a high-end bicycle (hybrid, road bike or e-bike)
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Use of a helmet
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Souvenir water bottle to keep
What's Included
Departure from Volterra, End of Tour
The bike tour ends in Volterra. Volterra does not have a train station or rental car agencies. However, Volterra is well connected by busses. The busses to Florence or Pisa take 2 hours. If you prefer we can book a taxi for you. We will be happy to assist you with your post tour travel plans.
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
What if it Rains?
On self-guided tours there is no van support. But, we do move your luggage. If it rains you can catch a ride with us when we move your bags, just call to make arrangements.
Siena Hotel Supplement During Palio
During the Palio (Siena's horse race) hotel prices triple. A surcharge of US$ 100 per person will apply for if you stay in Siena Jun 29-30, Jul 1-2, or Aug 13-16.
Use our Bike Bags (Panniers) and Save
Save US$ 50 per person. Pack what you need in our bike bags (panniers) and leave the rest of your luggage with us. We will deliver your remaining luggage to the last hotel.