Cycling in Tuscany: 6 Rides to Daydream About | Lucca Cycling Club

Cycling in Tuscany: 6 Rides to Daydream About

Alison Testroete

Hey, I'm Alison.

If you're planning or dreaming about cycling in Italy, my job is to make it happen for you.

Alison Testroete

Hey, I'm Alison.

If you're planning or dreaming about cycling in Italy, my job is to make it happen for you.

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 tour of Tuscany and I'm guiding you on six rides to add to your list of noteworthy achievements.

We'll start with the coast, then head inland and finish with northern Tuscany. If the lengths and elevations look tiring to you, 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.

Table of Contents
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    6. Bolgheri & Castagneto Carducci (Purple)

    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 (with her Orica team) has trained on 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. Climbing up towards the towns of Riparbella and Castellina Marittima is when you get wide-open views over the Tyrrhenian Sea.

    The most northern part of the route heads inward through the small Tuscan town of Lajatico, where Andrea Bocelli is scheduled to perform 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 was more afraid of me attempting the climb 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, Trattoria Senese (in Cecina and owned by Bettini’s parents).

    Viale dei Cipressi, Bolgheri
    The famous Viale dei Cipressi leading toward Bolgheri.

    5. San Gimignano + Volterra (Red)

    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).

    Via Francigena near San Gimignano. Photograph: Alison Testroete

    4. Chianti (Blue)

    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: Castello di Ama Winery, La Bottega del 30, Officina Della Bistecca.

    Winding road in Chianti, Tuscany

    3. Crete Senesi (Orange)

    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 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. Riding from Murlo to Sinalunga you may come across fields with white cows, home to 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 Leonina, Terme San Giovanni.


    2. Val d’Orcia (Green)

    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.

    Turning a blind eye entirely to the turnoff for Monte Amiata is suggested. I put it on the map just to stir the pot. A wiser idea would be to head straight for Bagni san Filippo, take a seat at one the shady outdoor terraces, and order a tall glass of Coke.

    The highlights of this ride (and what most people come to see) are Montepulciano, Monticchiello, Pienza, Chapel Vitaleta, and the surrounding 18 kilometers of strade bianche.

    Start/Finish: Bagno Vignoni, Montepulciano or Pienza.
    Dopo giro: Abbazia di Sant'Antimo, Posta Marcucci’s natural hot spring pools.
    Montalcino & Brunello wines: Poggio di Sotto and Salvioni.

    Intersection for Pienza, Tuscany
    Tuscany's Strade Bianche near Pienza. Photograph: Paolo Bendandi.

    1. Lucca (Yellow)

    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 counter-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, will be waiting 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: Giacomo Puccini Concert, Restaurants in Lucca.

    Switchback in Vergemoli
    Descending the Apuan Alps towards Barga. Photograph: Alison Testroete

    Special thanks to Brian Nygaard for the wine tips and historical cycling context. Brian’s a former pro-cycling press officer, team manager, and journalist with deep passions for Italy, cycling, and wine.

    Are you destined for cycling in Tuscany?

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