Self-guided cycling
7 nights,
single centre
Level: 2+ & 3
15.0Kg CO2e
Headwater
Navigation App
Complimentary
e-bikes
This seven-night holiday is, quite simply, unique in every way with breathtaking landscapes, UNESCO landmarks and medieval hilltop towns.
The cycle routes guide you through the heart of the San Gimignano region and its stunning surroundings. Ride through cypress dotted rolling hills, meander through valleys adorned with sunflower and poppy fields and explore the historic pilgrimage path, the Via Francigena. Visit Tuscan hilltop towns like Certaldo the birthplace of Boccaccio and Colle di Val d'Elsa famous for its crystal making and for being the birthplace of Arnolfo di Cambio, the architect behind Florence's Duomo and Palazzo Vecchio. There will be ample opportunities to stop at wineries and farms dotting the area allowing you to sample the best local produce and to recharge your batteries.
Your stay will be in a beautiful family run hotel, where you are assured a warm welcome. Located a short ride outside of San Gimignano, you will have multiple chances to visit the historic hilltop town also nicknamed as the 'Medieval Manhattan' due to its iconic skyline of ancient towers. It is a must see destination for any visitor to Tuscany.
After a day of discovery, unwind by the serene pool overlooking the picturesque Sienese hills, then enjoy the authentic Tuscan dishes at the hotel's restaurant.
Most of the cycling is along paved roads but some routes you will be cycling along “strade biache”; while these renowned white gravel paths add unique charm to your trip, they can also be strenuous. An E-bike has been included in the trip due to the hilly nature of the routes.
During the summer months of July and August there is a notable increase in traffic to this part of Tuscany. If you prefer quieter roads and to avoid very hot weather, it is better to come outside these months.
Arrive at your accommodation where you will be met for a bike fitting and a briefing on the local area. Should time allow, why not unwind by the hotel's pool and admire the picturesque Tuscan countryside.
You stay at Hotel Casolare Le Terre Rosse.
Pool
Hairdryer
WiFi
TV
Aircon
Safe
You will spend 7 nights at the Hotel Casolare Terre Rosse in the heart of the soft hills of San Gimignano. The hotel combines Tuscan features with a modern day comforts so you can be perfectly relaxed during your stay. The hotel is surrounded by beautiful greenery and has an outdoor swimming pool where guests can enjoy the sunshine.
With half board included in your stay, you’ll enjoy a variety of regional dishes which are all focused on seasonal and local ingredients. During warm evenings dinner can be served in the beautiful courtyard providing a perfect setting to unwind in.
Mornings will start with a tempting buffet, with international breakfast options such as eggs, breads and cold cuts or there is also a choice of Italian breakfast items such as homemade cakes, pastries and jams. The abundant buffet is sure to fuel you for the day ahead.
After breakfast set off on your first day adventure to explore the surrounding Castelvecchio Nature Reserve. Today's route gives you the perfect opportunity to immerse yourself into the Tuscan countryside. If you are lucky enough, you might catch a glimpse of the rare peregrine falcon that has made this nature reserve its home. Towards the end of your cycle, you will have the chance to stop off in San Gimignano, it is most famous for it's medieval towers, reputed to have come into being because of a bitter rivalry between neighbours. You can climb up some of them and the views of the neighbouring valleys make it well worth the effort!
Set out on the historic Via Francigena, an ancient pilgrimage route dating back to the Middle Ages that once led travellers to Rome. Today, this iconic path offers cycling through a scenic mix of paved and unpaved roads, framed by wildflowers and olive groves. After riding past rows of vineyards, why not take a break at a nearby winery to enjoy a glass of fresh Vernaccia.
This morning you will pedal through tree-lined meadows and a valley of poppy and sunflower fields to the hilltop town of Colle di Val d'Elsa. Internationally renowned for its crystal production, it is Italy's biggest producer of fine glass and crystal. Make sure you visit Colle Alto- the panoramic, medieval old town is the perfect location to enjoy a local glass of chianti accompanied with some traditional crostini.
With a regular bus service running from San Gimignano to Siena (1 hour), today is the perfect opportunity to explore the beautifully preserved city of Siena. Begin your visit at Piazza del Campo, the town's iconic shell shaped square, famous for the palio horse race. Climb the Torre del Mangia for panoramic views and don't miss the stunning striped 14th century gothic cathedral.
Today's ride takes you to Gambassi Terme, a well preserved spa town with cobbled streets, 12th century church and lovely shaded gardens, which was once the key stop for pilgrims travelling along the Via Francigena. After a brief visit, continue your ride to the enchanting town of Certaldo, the birthplace of the renowned writer Boccaccio. Don't miss the chance to take a scenic funicular ride up to Certaldo Alto, the medieval heart of the town, where you can enjoy sweeping views of the stunning Val d'Elsa. Visit Palazzo Pretorio, the town's most iconic landmark, adorned with frescoes and the coats of arms of the various Governors sent here from Florence.
Explore the small hamlets that surround San Gimignano on today's adventure. You will also visit the old town of Poggibonsi which has always been an important crossroads due to its strategic position between Siena and Florence. Above the town are the ruins of the 15C unfinished fortress, and you will pass the lovely Basilica di San Lucchese which has beautiful views across to San Gimignano's iconic towers. Loop back to San Gimignano on the panoramic, white gravel strade bianche that crisscross the Tuscan landscape, before your final dinner at your hotel.
After breakfast leave San Donato
These tour only prices are based on two people sharing. Single supplement from C$460.
Call now to speak to our specialist team at 0044 1606 720199 or email us at sales@headwater.com for enquiries or to book your trip.
Self-guided cycling
7 nights,
single centre
Level: 2+ & 3
15.0Kg CO2e
Headwater
Navigation App
Complimentary
e-bikes
