Cycling in Tuscany: 7 Dream-Worthy Rides | Lucca Cycling Club

Cycling in Tuscany: 7 Dream-Worthy Rides

Your calendar is wiped clean: no errands, no Zoom meetings, no important emails (except mine), and certainly no work. The skies are staring at you with deep blue eyes and the sun’s tugging at your heartstrings, “cycling in Tuscany today?”

Just say “yes”.

Because today you’re going on a bike tour of Tuscany and I’m guiding you on seven rides to add to your list of noteworthy achievements.

We’ll start with the coast, pop over to The Island of Elba, then head inland and finish with northern Tuscany. If the lengths and elevations look tiring, these daydream-worthy rides can easily be amended into multi-day tours. It’s our expertise.

Now, let’s see what cycling in Tuscany dreams are made of.

Bolgheri and Castagneto Carducci (Green)

Starting with the Etruscan Coast, Paolo Bettini country is off most people’s radars (including mine until recently). It’s chalked full with not only archeological sites, but some of Italy’s most important wines, thermal spas, and of course, small country roads.

Men’s professional teams like Mapei and Quickstep would train here before or after GP Costa Etruschi — once the first race of the Italian calendar. Not only Paolo Bettini but also Annemiek van Vleuten has ridden these roads to later become World Champion.

The first half of the ride winds up and over the rolling hills, past vineyards surrounding Bolgheri and through the cypress-lined Viale dei Cipressi. You get wide-open views over the Tyrrhenian Sea by climbing up towards the towns of Riparbella and Castellina Marittima.

The most northern part of the route heads inward through the small Tuscan town of Lajatico, where Andrea Bocelli performs at the outdoor Teatro del Silenzio. This is also the area surrounding Volterra which you’ll see in the distance climbing the ten tight switchbacks of Micciano.

I’ll admit, I was not at my best on this section of road. Out of water for miles with no fountain in sight, I stopped at an agriturismo where an elderly gentleman feared me attempting the climb more than contracting Coronavirus. He reminded me, however, that my compass was on point — cyclists and professional teams pass by often because there are so few cars on this climb.

My 200 km route, confirmed by the concern in the man’s eyes, was cut through the valley and past the old Etruscan town of Sassetta — for another day.

Start/Finish: Bolgheri, Castagneto Carducci or Bibbona.
Dopo giro: Le Macchiole winery.

Island of Elba (Purple)

The Island of Elba is so small you can ride the whole island in a day if you wanted to. You’ll take an hour ferry from Piombino on mainland Tuscany to Portoferraio with or without a car.

For convenience and because Portoferraio is beautiful, we’re starting this ride there. As you’ll come to expect cycling in Tuscany, there’s zero flat, including Elba.

Monte Capanne is the highest mountain on the island, but we’re forfeiting the peak for the entire pie on this ride. In three days (two nights), you’d cycle all the bases including Perone — the southwest side up Monte Capanne.

Back to our route. We’ll ride halfway up Monte Capanne to Poggio then descend to the coastal road hugging the island’s southwest side.

Embarrassingly enough, given how close Elba is to Lucca, I still haven’t been, so I consulted LCC guide, Enzo. He’s a fun-loving, beach kinda guy and makes a yearly trip to the island.

According to Enzo (and in his words), the coastline through the town of Pomonte is “bellissima, strapiombo, stupenda. La costa e panorama più bella che c’è.”

In a nutshell, he’s telling us this coastline and panorama is absolutely unreal.

The second half of the ride is a mix of inland and coastal roads but am sadly suffering a gap in personal experience. If you have more than a day, you’ll discover some of the best beaches with the clearest waters in all of Tuscany. Go early or late summer to avoid the crowds.

Start/Finish: Portoferraio.
Dopo giro: Sansone Beach, Cavoli Beach and Beach of Fetovaia.

San Gimignano and Volterra (Orange)

I like starting this ride in Siena because it’s beautiful and more authentically Italian. In other words, taking on this ride through San Gimignano and Volterra is unavoidably touristy. Yet you and I both know that the bike diffuses congregations with cameras in hand, so it’s still a noteworthy achievement.

Monteriggioni, a fully intact walled castle, is tourist stop number one. This tiny two-kilometer detour is worth seeing if anything to add context to Dante Alighieri’s The Divine Comedy.

To get from Monteriggioni to San Gimignano is a Top Guide’s Rubik Cube. Anybody who’s been here knows that Poggibonsi and its surroundings can only be navigated with a knight. And the knight on this ride is Via Francigena — the old train tracks turned gravel bike path.

It’s clear sailing until tourist stop number two, San Gimignano, then around the natural parkland and nine kilometers up to Volterra (tourist stop number three). When you imagine cycling in Tuscany, it’s here through rolling hills, vineyards, and golden wheat fields that add depth and dimension to otherwise ordinary sightseeing.

Start/Finish: Siena, San Gimignano or Volterra.
Dopo giro: Salefino Vino e Cucina (Siena).

Chianti Classico (Yellow)

Chianti needs no introduction. People flock here for its good food, wine, and riding. Like the Crete Senesi, anybody and everybody on a bike pass through Chianti.

Starting from the heart at Radda in Chianti, this figure-eight loop covers pretty much everything. Passing through Castellina and the descent via Fonterutoli are vineyards and wide-open spaces. It loops back, taking a few gravel segments, including the most famous of them all, Castello di Brolio.

There’s a perfectly paved parallel road, but the beauty of cycling is all the stories we gather from taking the path less traveled.

A particularly unforgiving beast of a road less traveled goes by the name of “Salita del Albola”, after crossing Radda for the second time. It’s unbelievably beautiful, yet has to be Chianti’s steepest climb with the shade of a handful of skinny cypress trees.

Other highlights include Gaiole in Chianti, Greve in Chianti, and Panzano in Chianti — where you’ll find the world-famous butcher.

Start/Finish: Radda in Chianti, Greve in Chianti, Gaiole in Chianti, or Panzano.
Dopo giro: Winery San Giorgio a LapiOfficina Della Bistecca.

Crete Senesi (Red)

The Crete Senesi is the heart and soul of Tuscany and Italian cycling. From Giro d’Italia, L’Eroica, Strade Bianche Eroica Pro to the old Roman road, Via Francigena, anything and everything important in cycling passes through the Crete Senesi.

Parting from the town of Asciano you’ll take the first gravel sector at Monte Sante Marie through Castelnuovo Berardenga, then the second at San Martino in Grania — both shown in the photos below.

For gravel bike lovers, the Sienese clays are your long, lost home. Often missed entirely by road cyclists is the sculpture, Site Tranitoire—place of passage—installed by the French artist Jean-Paul Philippe to convey the three basic positions of human existence (sit, stand, or lie down).

Once you’re in the small fortified town of Murlo, you’ll be just shy of halfway and the perfect place for lunch at Murlo’s one and only restaurant. Crossing the fields from Murlo to Sinalunga, you’ll find herds of white cows, Tuscan’s Chianina cattle.

Yet more gravel backroads (not out of necessity) lead to Rapolano Terme, one of many Tuscan towns named after its natural hot spring.

Start/Finish: Asciano or Castelnuovo Berardenga.
Dopo giro: Ristorante Castello di LeoninaTerme San Giovanni.

The spectacular Crete Senesi just before sunset. Photograph: Antton Miettinen

Val d’Orcia (Red #2)

If you’re excited by the idea of cycling through a World Heritage Site, Val d’Orcia is for you. You don’t even have to like culture or heritage to appreciate this ride or cycling in Tuscany in general.

There’s no best for last in Val d’Orcia: it’s like playing your ten favorite songs on repeat. The trick is, a little goes a long way — I write from personal experience.

From Bagno Vignoni, there’s not much of a warm-up (and I doubt you’ll need it in 30 plus degrees) because the stone tower at Rocca d’Orcia is where this ride is headed. In fact, the first 41 kilometers are all uphill, as high as 1,738 m (5,702 ft), the peak of Monte Amiata.

Skipping over Monte Amiata is suggested, but then again, not that dumb of an idea. Whichever option you choose, Bagni San Filippo is standing by with a tall glass of Coke on a shady outdoor terrace.

The highlights of this area (and what most people come to see) are Montepulciano, Montalcino, Pienza, Chapel Vitaleta, and endless clusters of famous cypress trees.

Start/Finish: Bagno Vignoni
Dopo giro: Abbazia di Sant’AntimoPosta Marcucci’s natural hot spring pools.
Montalcino & Brunello wines: Poggio di Sotto and Salvioni.

Two cyclists riding on a gravel road between trees.
One of many beautiful gravel roads near Pienza. Photograph: Antton Miettinen

Lucca (Blue)

What sets Lucca (and this ride) apart from the rest of Tuscany are the mountains: Apuan Alps, Apennine, and Pistoian Mountains.

There are a number of different ways to reach them — this ride takes the quickest path. At just 25 kilometers, you’re in the thick of the Apuan Alps or the Tuscan boonies.

The route runs clockwise along the Pania della Croce, the highest peak in the Apuan Alps. If there’s a time when you want (or need) to truly ride solo, this is it. You’ll encounter very few cars or fellow cyclists here. The unexpected bonus is the newly paved roads as of 2019.

You’ll descend into Garfagnana — the valley between the Apuan Alps and Italy’s north-to-south Apennine mountain range. Barga, a medieval village, waits patiently for you on the other side. It’s a hillside town with a church up top. I love bringing my guests there to see Monte Forato (mountain with a hole) and a view of the whole Garfagnana valley.

Start/Finish: Lucca or Barga.
Dopo giro: Things to Do in LuccaRestaurants in Lucca.

Winding mountainous road.
The switchback climb leading up to Vergemoli. Photograph: Antton Miettinen

Will you soon be cycling in Tuscany?

These seven rides don’t scratch the tarmac of what cycling in Tuscany offers, yet I hope they get your wheels turning. If you have just one day in any of these areas, I created a beautiful Tuscany Route Collection just for you.

Two cyclists riding next to a building.

6 thoughts on “Cycling in Tuscany: 7 Dream-Worthy Rides”

  1. I landed on Alison’s page after searching for inspiration where to spend my holidays. As always it should include nature and cycling as much as I can. Alison’s writing and representation of cycling of Tuscany inspired me.

    I finally rode around 70 % of the original distances at my own pace of the routes 1. Lucca (blue) and 7. Bolgheri & Castagneto Carducci (Green) and visited Lucca which attracted me because I read about it here. If you are unsure of your fitness level these tracks are also a good test and maybe inclube plan b’s to take shortcuts 😉

    I want to say this: WOW
    I will never forget the feelings during my cooldown round around Lucca’s city wall with all the impressions in my head of cycle tracks meandering through paradise and of the breathtaking views I just witnessed.

    Thank you Alison/LCC-Team

    1. Alison Testroete

      Thanks so much for sharing, Jonas. It’s top honor to recruit new Lucca aficionados. Please come back when you can!

  2. Tried the blue route north of Lucca in the mountains. Very nice route demanding for a family father, I took it counter-clockwise. Thanks Alison for good blog and route suggestions as well as friendly replies by mail. Highly recommend!

Leave a Comment

Your email address will not be published. Required fields are marked *

Shopping Basket