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Tuscany More Miles for Less: Classic Tuscany

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Tuscany More Miles for Less: Classic Tuscany

Tuscany More Miles for Less: Classic Tuscany

The Tuscan Lands of "Vino"
The Arno Valley, Chianti and Montalcino

Highlights

  • Spin along the delightful Sette Ponti Road
  • Cross the Chianti hills on the Strade del Vino, to Gaiole and Radda
  • Spin to Monte Oliveto Maggiore Abbey and also Brolio Castle for an optional wine tasting
  • Enjoy a walk in the Medieval Village of Il Borro
  • Discover the UNESCO World Heritage Site of Val d’Orcia
  • Ride to Pienza, Montepulciano and Montalcino, hometown of the most famous Tuscan red wine, the Brunello

Description

We'll zigzag across the Arno and the surrounding hills and valleys south of Florence. The Chianti area provides great wine, and incredible roads for biking on. Savor both as we pass through capital towns of wine production: Gaiole and Radda.

The second part of the trip unfolds in the southern part of Tuscany, known as the Val d’Orcia, a UNESCO World Heritage Site. We’ll enter Pienza and Montepulciano through magnificient gateways and enjoy strolls along charming alleys lined with small pecorino cheese shops, artisans’ workshops and centuries-old palaces.  Our last ride will stretch as far as Montalcino, a fortress dominating the view on the surrounding hills, and of course the vineyards of Brunello red wine.

   
Day 1–2: Arno Valley, Laterina and sette ponti road
Arno Valley, Laterina and sette ponti road

Day 1: Ancient olive groves, manicured landscapes and Etruscan sites dot the warm-up route around Laterina, Casanuova and Ponticino.
Day 2: The Strada dei Sette Ponti - the Road of Seven Bridges - makes for a beautiful ride through the sunny Pratomagno range. Tiny villages are linked by this route, dotted with fig trees, vegetable farms, and vineyards.

Day 3: The Chianti Countryside and Rapolano
The Chianti Countryside and Rapolano

Here is where your postcard-perfect image of Tuscany will come to life! The distinct cypress trees, vineyards and ancient stone walls will surround you along the entire route in the Chianti area en route to Rapolano.

   
Day 4–5: Montefollonico, Montepulciano, Pienza and Montalcino
Montefollonico, Montepulciano, Pienza and Montalcino

Day 4: Today’s ride goes through the famous area of “Le Crete Senesi” literally ‘Siennese clays,’ rolling hills where the distinctive grey colouration of the soil gives the landscape an appearance often described as lunar. After a cappuccino in Asciano we continue on to the Abbey of Monte Oliveto Maggiore, a large Benedictine monastery founded in 1313. Our final destination is Montefollonico, a tiny medioeval village perched on a cliff overlooking the Val di Chiana and the Trasimeno Lake.
Day 5: Spin to Pienza for a stroll and a cappuccino in the beautiful town centre before descending into the UNESCO Site of Val d’Orcia to cruise through wheat fields and vineyards. Visit Montepulciano ancient city centre before the last climb back to the hotel or go further west to Montalcino.

Day 6: Arrivederci!

You can extend your stay in Tuscany or take a taxi to Chiusi train station, where you can make your connections.

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All Levels

You’re potentially interested in any level of trip and don't want your site experience tailored to any specific level.

Easy

You’re new to biking, or you just want to take it easy with lots of stops to take pictures and explore and no one hurrying you along. Expect a leisurely pace over generally flat terrain.

Average distance per day: 18-35 miles.

Athletic Beginner

You’re not a fanatical rider, but you exercise regularly and enjoy a leisurely day’s spin on your bike. You might want to graduate to “intermediate” one day, or not. The pace is relaxed but the terrain gently rolling, more ups and downs, more vistas and valleys than Easy tours.

Average distance per day: 35-45 miles.

Intermediate

You’re active on your days off, and recreational biking is most likely your weekend sport of choice. You love to ride and it shows in your endurance and strength. A steady but active pace, with opportunities to push yourself and some challenging climbs, with great descents over rolling terrain. (These folks ARE cyclists, they are usually pretty serious cyclists but do not train at the expert level.)

Average distance per day: 40-50 miles.

Expert

You crave vigorous pacing, challenging climbs and thrilling descents. You crave longer mileage with lots of hills and descents, varying terrain, and a mountain pass or two only makes it better.

Average distance per day: 45+ miles.

Family

If you have kids under 16, we have great options for you! With fewer hotel changes, easier biking and wheels for all ages, we've got your ideal active family holiday.

Average distance per day: 20–30 miles.