Toscana Pro

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Toscana Pro bike Tour - Itinerary
Day 1


Your guides will greet you in Florence and transfer you to our first luxury hotel in Bagno a Ripoli, near the famous River Arno. After toasting our arrival with a welcome Prosecco, we’ll get fitted to our Cannondale SuperSixes. Our route takes us through the forests, vineyards, and olive groves of the hills behind Florence. Ride back to the hotel to relax or (timing permitting) watch the Under-23 championship race roll through Fiesole as the stars of the future complete the final circuits before the finish in Florence. Tonight we’ll introduce you to the best Tuscan cuisine at our favorite local restaurant.

Meals: Light Lunch / Dinner
Mileage: 29 miles / 46 km
Climbing: 3,545 feet / 1,080 meters
Destinations: Florence, Bagno A Ripoli, Santa Brigida

Day 2


Enjoy an outdoor breakfast in La Chiusa’s courtyard Set off today for the heights of the Apennine Mountains. These passes act as a training ground for countless pros and we’ll soon see why. The roads are truly a cyclist’s paradise: no traffic, fun curves, great views, and smooth pavement. Warm up on a 600-foot climb to Fiesole before continuing over to Borgo San Lorenzo and taking on the winding switchbacks of the 2,000-foot ascent over the Passo del Giogo. Regroup and recharge in Firenzuola before heading back to Fiesole over the scenic Passo della Futa. This afternoon we’ll have the opportunity to see the next World Champion crowned as the pros finish their race with a circuit through Florence and Fiesole.

Meals: Breakfast / Lunch / Dinner
Mileage: 80 miles / 128 km
Climbing: 9,364 feet / 2,855 meters
Destinations: Borgo San Lorenzo, Passo del Giogo, Passo della Futa

Day 3


Today we will cross the heart of the Chianti region between Florence and Siena. Head into the classic Tuscan landscape that inspired Renaissance painters like Leonardo da Vinci. Olive trees, vineyards, and villas line the route as we ride through the hilltowns of Panzano and Radda. In Radda our friend Monica will serve us a lunch of fresh bruschettas, salads, and pastas at her local restaurant. The rest of the ride follows the ridgeline before ending at our stunning hotel and winery, Borgo di Vescine, for an intimate wine tasting and dinner.

Meals: Breakfast / Lunch / Dinner
Mileage: 241 miles / 66 km
Climbing: 5,213 feet / 1,589 meters
Destinations: Strada, Panzano, Radda

Day 4


Ride out into the Chianti morning toward Castellina, perched above the Elsa Valley. Thrill at the 19-kilometer descent from here to Poggibonsi. Then climb back to the hilltop town of San Gimignano, enjoying a stunning approach as the town’s towers come into view. We’ll park the bikes and explore the medieval streets. Enjoy lunch in town and indulge at the world champion gelateria in the main square. Then we’ll head south on quiet roads through San donato and Castel San Gimignano before turning for home, climbing back into Castellina through some of Chianti’s largest vineyards. Tonight we’ll take you to Radda where you can choose between the excellent local restaurants.

Meals: Breakfast / Lunch
Mileage: 54 miles / 86 km
Climbing: 3,661 feet / 1,116 meters
Destinations: Castellina, Poggibonsi, San Gimigano, Colle Val d’Elsa

Day 5


Saddle up for a big ride. Today we’ll leave the Chianti region and cross the stunning landscape known as the Crete Senesi. The soil here is only suitable for grazing and growing wheat, allowing for panoramic views stretching from Siena to the slopes of Monte Amiata. Lunch will be a gourmet picnic with fresh, cyclist-friendly foods. Leaving the Crete we’ll return to the woods and vineyards as we climb to the hill-town of Montefollonico, where we’ll stay in our friends’, dania and Umberto, converted olive mill, enjoying the peace and scenery of this magical spot. Tonight dania will treat us to a refined Tuscan dinner at her renowned restaurant.

Meals: Breakfast / Lunch / Dinner
Mileage: 52 miles / 85 km
Climbing: 6,072 feet / 1,851 meters
Destinations: Monteaperti, Asciano, Trequanda

Day 6


Set off today for Tuscany’s pre-eminent climb: Monte Amiata. Cycle through the historic town of Pienza and across the Orcia Valley on a 19-kilometer approach to the base of the mountain. The next 27 kilometers are almost all uphill. Enjoy a well-earned lunch in the restaurant at the summit before the descent and the final climb back to Montefollonico. Tonight we’ll enjoy a private tour of our friend and local winemaker Vittorio Innocenti’s cantina. Taste his traditional Vino Nobile and Vin Santo before settling in for dinner at our favorite local restaurant right next door.

Meals: Breakfast / Lunch / Dinner
Mileage: 70 miles / 112 km
Climbing: 5,853 feet / 1,784 meters
Destinations: Pienza, Orcia Valley, Monte Amiata, Montefollonico, Vittorio Innocenti Winery

Day 7


Say goodbye to Tuscany any way you see fit. Opt to sleep in and enjoy a cappuccino on the terrace or take a final ride along the cypress-lined roads to Montepulciano and Montichiello. Your guides will take you to the Chiusi train station at midday to see you off.

Meals: Breakfast
Mileage: 25 miles / 40 km
Climbing: 1,687 feet / 514 meters climbing (Optional ride)
Destinations: Montepulciano, Montichiello, Orcia Valley