Tuscany Challenge

Day One: Montichiello Loop
Welcome to Tuscany.  Your guides will pick you up at the train station in Chiusi and drive you up into the hills that we will call home for the next week.  After toasting your arrival with a welcome Prosecco, you’ll get fitted on your bike and take off for the first ride.  Our route takes us along a rolling ridge past the hill town of Montepulciano before starting the first of many hair-raising descents.  This particular one follows the famous s-curves of the cypress-lined road above Montichiello before dropping you into the scenic Orcia Valley.  The climb back to the hotel will be the first test of your legs and will be well-rewarded with an intimate Tuscan evening with our friends Dania and Umberto, the owners of the luxurious villa La Chiusa. Dania runs the kitchen of this Michelin-starred restaurant, while Umberto will be eager to welcome you as a friend and show you how to live like a local. Enjoy the breathtaking views from this ancient olive mill while savoring the region's gourmet specialties, grown on La Chiusa’s estate, then unwind and let this heavenly Tuscan experience take over.

Meal: Dinner
Destinations visited: Montefollonico & Montepulciano
Distance cycled: 41 km / 26 miles   Total Climbing: 1687 ft

Day Two: Monte Amiata
Enjoy an outdoor breakfast in La Chiusa’s courtyard before setting off for Tuscany’s pre-eminent climb: Monte Amiata.  This 1753m dormant volcano is the highest peak in Tuscany and dominates the surrounding countryside. It has been featured in the Giro D’Italia and is a rite of passage for local riders.  Our assault on the summit will begin in Montefollonico.  After cycling through the historic town of Pienza and across the Orcia Valley on a 19 km approach, you arrive at the base of the mountain.  The next 27 km are almost all uphill, as you climb out of the cultivated farmlands into the thick chestnut forests that sheltered escaped Allied prisoners in WWII and have provided sustenance for the local villages for centuries.  After completing the final switchbacks, you will arrive at the finish where you will enjoy a well-earned lunch in the restaurant at the top of the ski slope.  Admire the unmatched views in every direction before beginning the epic descent and the final climb back to Montefollonico.  Back in Montefollonico, we’ll have a very special private tour of our friend and local winemaker, philosopher and playwright, Vittorio Innocenti’s cantina.  We’ll taste his traditional Vino Nobile and Vin Santo in his garden with the breathtaking Chiana Valley as a backdrop.  Dinner is right next door at the warm, rustic Botte Piena.

Meals: Breakfast/Lunch/Dinner
Destinations visited: Pienza, Abbadia San Salvatore, Monte Amiata,
Distance cycled: 112 km/ 70 miles  Total Climbing: 5853 ft
 

Day Three: Siena and the Crete Senesi
Today is your opportunity to let your legs recover from Amiata.  We will spin along a stunning route, through forests and pastures on the way to the sleepy town of Trequanda.  After Trequanda, the landscape opens up as we enter the scenic countryside of the Crete Senesi.  These treeless hills are predominantly used for growing wheat and the road along the ridges is known as one of the most heavily photographed routes in the world.  Along the way we will stop for a picnic lunch before continuing to Siena.  Siena is a gem of a medieval city with beautifully preserved Gothic architecture.  The city is built around the Piazza del Campo, regarded by many as the most beautiful piazza in all of Italy. Here you’ll have time to shop while exploring the many hidden medieval walkways before joining the guides at one of our favorite local restaurants for dinner. 

Meals: Breakfast/ Gourmet Picnic/Dinner
Destinations visited:  Trequando, Asciano, Arbia, Siena
Distance cycled: 51 km/ 32 miles Total Climbing: 1867 ft Optional 30 mile add-on to Montalcino

Day Four: San Galgano
From Siena, take the back route into the countryside following a quiet lane, lined with stone walls, vineyards and olive trees.  Arriving in San Casciano, begin a wild descent to the valley below before beginning a wooded climb into one of Tuscany’s largest forests.  After cresting the hill, you’ll cycle to the medieval abbey of San Galgano.  This abbey once dominated the surrounding countryside, its monks acting as accountants and diplomats for the Sienese city-state.  Now, the roofless main church is one of the most evocative sites in all of Italy.  In the summer there is a popular series of concerts and operas held here.  We’ll have a picnic lunch and explore the grounds before looping back to Siena. The night is yours and your guides will be happy to point you to a favorite local trattoria for dinner. 

Meals: Breakfast/Lunch
Destinations visited: San Casciano, San Galgano, Siena
Distance cycled: 81 km/ 50 miles  Total Climbing: 3346 ft

Day Five: Crossing Chianti
Leaving Siena, you’ll cycle north into the famous hills of Chianti.  Passing rows of olive and cypress trees, we’ll climb a ridge and break out of the trees as we ride through the gorgeous Chianti Classico estates of Bossi and San Felice.  From here you’ll start the day’s first big climb up over the main Chianti ridgeline, with grades reaching over 15%, followed by an exhilarating descent into the town of Montevarchi far below.  We’ll stop for lunch at a great local restaurant and wine bar before starting the day’s second big climb back into the Chianti hills.  From Montevarchi, the road climbs steadily, regaining the top of Chianti’s main ridgeline near the medieval abbey of Badia a Coltibuono only after a few tough final switchbacks.  The rest of the ride follows this ridge, passing through the wine village of Radda in Chianti before ending at our stunning hotel and winery, Borgo di Vescine, – a serene 13th century hamlet - for an intimate wine tasting with the winemaker, Vincenzo, and dinner.   
 
Meals: Breakfast/ Lunch/ Dinner
Destinations visited: Pianella, Bossi, San Felice, San Gusme, Montevarchi, Radda in Chianti
Distance cycled: 80 km/ 50 miles   Total Climbing 4344 ft

Day Six: San Gimignano Loop
After breakfast, ride out into the peaceful Chianti morning towards the town of Castellina, perched above the Elsa Valley.  The 19 km descent from here to the town of Poggibonsi below is sure to leave you grinning and things just keep getting better as your guides will lead you the back way to the famous hilltop town of San Gimignano.  The approach is stunning as the town’s towers, at first only visible on the horizon, grow increasingly taller as you pedal along the vine-covered ridgelines.  A final climb brings you to the town walls where we will park the bikes and take time to explore the medieval streets.  Your guides can recommend a restaurant for lunch on your own and take you to the world champion gelateria in the main square.  Leaving San Gimignano, we’ll head south on quiet roads through San Donato and Castel San Gimignano before turning for home.  The day ends with a gorgeous climb back into Castellina through some of Chianti’s largest vineyards.  Tonight we’ll celebrate our final dinner at our favorite local restaurant in Radda.

Meals: Breakfast/ Lunch/ Dinner
Destinations visited: Castellina, Poggibonsi, San Gimignano, Colle Val d’Elsa
Distance cycled: 86 km/ 54 miles  Total Climbing: 3661 ft
 
Day Seven: Florence
Saddle up for your final ride.  Florence is much lower than our hotel, so we will finally get to cash in on all the climbing with a huge net downhill into the Tuscan capital.  Along the way, you will ride through the heart of Chianti passing quaint towns such as Panzano and Greve.  Outside of Florence we will hop onto a series of quiet country lanes, lined with stone walls as we wind our way up to the city gates.  Once inside the walls, most cars are prohibited, and we will pedal through the historic center to the trip finish at the train station.  Here we will say goodbye as you head off to your next destination.

Meal: Breakfast
Destinations visited: Panzano, Greve, Florence
Distance cycled: 50 km/ 30 miles  Total Climbing: 1280 ft

TRIP TOTAL: 500 KM/ 312 MILES  / 21966 ft Total Climbing