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Cycling Tuscany: Chianti & Siena
Tour Location
Tour Information
Luggage Transfer, Phone Support, Maps or GPS
8 days
Bike Options:
Bike hire available
Tour Language:
Cost From:
Tour Distance & Dates
Mar, Apr, May, Jun, Jul, Aug, Sep, Oct, Nov
Tour Operator:
Macs Adventure

Cycling Tuscany: Chianti & Siena

8 Days Moderate

Experience the very best of classic Tuscany on a self-guided cycle tour. Take to two wheels and cycle bella Italia, discovering picture-postcard Medieval and Renaissance hill-top villages, accompanied by sumptuous cuisine and the famed Chianti, Brunello and Nobile wines.

Each day you will be cycling at your leisure through impossibly pretty scenery, characterised at first by vineyards and verdant farmland which lead to contrasting cypress-lined country roads, the UNESCO World Heritage Landscape-listed Val d’Orcadia and the grey hues of the ‘Crete’ region.

Your Tuscan adventure starts with an incredible first day’s cycling; visit the fortified town of Monteriggioni, before heading to one of Italy’s most spell-binding locations—San Gimignano with its many towers. Each day you’ll reach traditional villages perched atop rolling hills filled with stunning red brick and earthen-coloured buildings, with roofs baked by the Tuscan sun. Highlights include magical Siena, the thermal-spa town of Bagno Vignoni and Pienza, as well as photogenic Montichiello and Montepulciano.

Cool churches, abbeys and monasteries await you, where Gregorian chants drift through the air and create a special ambience. Take time to reflect at the Monte Oliveto monastery and peaceful abbey of Sant’ Antimo. You’ll also pass through towns located on the route of the ancient Via Francigena pilgrimage. And the end to each perfect day’s cycling? You’ll certainly have earned a glass or two of full-bodied Italian red accompanied by a dish garnished with local pecorino cheese and truffles! Tuscany is well known for its steep hills and therefore this trip will appeal to those with a good level of fitness, with daily distances ranging from 35 to 46 kilometres.
Double Occupancy / Twin Share
Single Supplement: Available
7 Nights accommodation in rooms with private facilities in hotels, an agriturisimo (country hotel) and a bed and breakfast accommodation
Transfer on Day 8 from Montepulciano to Chiusi
2 Dinners (at Villa San Lucchese and Pieve a Salti)
7 Breakfasts
Information pack, route notes & maps
Baggage Transfers
Welcome briefing and bike hire fitting
24/7 Emergency phone support
Lunches, dinners (except on 2 nights aforementioned), snacks and drinks
Travel to Poggibonsi / from Chiusi
Travel insurance
Admissions or entrance fees
Public transport or additional transfers
Rental of bike/s
Bike Hire: 27-gear hybrid or road bike, with rear rack, 1 rear pannier, odometer, pump, repair kit, water bottle and map folder
Additional night/s at any of the accommodations on the way or other destinations in Italy
Solo cyclist or single room supplements
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