The Most Beautiful Driving Routes in Tuscany: 6 Routes + Map

The Most Beautiful Driving Routes in Tuscany

Tuscany is perfect for road trips: quiet, winding roads, cypress-lined avenues, medieval villages, and a view every 10 minutes that makes you want to pull over on the spot. In this article, you’ll find the most beautiful driving routes in Tuscany (6 routes + 1 bonus), including distances, highlights, photo stops, accommodation tips, and sustainable road trip hacks.

Quick choice: Which route is right for you?

View of Tuscany's Chianti Region

First time in Tuscany? Here’s how to plan your trip smartly

If you’re new to Tuscany, choose one base in Chianti or Siena and take day trips from there. If you’ve been there before, Val d’Orcia and the Maremma are often even more impressive (and quieter once you steer clear of the well-known hotspots).

My top tip: plan to drive fewer kilometers than you think. Tuscany is at its best when you have time to stop at those unexpected scenic spots.

1. The Chiantigiana (SR222): the quintessential route through Chianti

The perfect first route (and honestly, even if you’ve been there before).

Route (can be shortened or extended as desired)
Florence – Greve in Chianti – Castellina – Radda – (optional: Gaiole) – Siena

Quick Facts

  • Road number: SR222 (Chiantigiana)
  • Distance: ± 69 km Florence–Siena Visit Tuscany
  • Why it’s so beautiful: vineyards, olive groves, cypress trees, borghi

Stops That Make a Difference

  • Greve in Chianti (market square + atmosphere)
  • Radda/Castellina (medieval, perfect lunch stops)
  • Bonus loop: Gaiole in Chianti (castles and fewer crowds)

Accommodation Tip (Chianti): Fattoria di Maiano

2. Val d’Orcia UNESCO Route: Tuscany at its most photogenic

The Val d’Orcia has been a UNESCO World Heritage Site since 2004. Here, you’ll experience that “Tuscan feeling” everyone thinks of: rolling hills, solitary cypress trees, and light that changes throughout the day.

Route (approx. 60 km, plus all impromptu stops)

  • SP14/SP146: Montalcino – San Quirico d’Orcia – Pienza
  • SR2: San Quirico – Bagno Vignoni – (toward Rocca/Castiglione d’Orcia)
  • SP88: toward Monticchiello
  • on to Montepulciano (via local roads)

Highlights Along the Way

  • Pienza (Renaissance and Pecorino)
  • San Quirico d’Orcia (charming historic center)
  • Montalcino (Brunello)
  • Bagno Vignoni (hot spring in the square)

Best time to visit

  • May–June (green and fresh)
  • Sept.–Oct. (harvest, golden light)

Read more here about the most beautiful route through the Val d’Orcia.

3. Casentino: Wooded Tuscany with castles and tranquility

Casentino is the Tuscany that many people miss: cooler air, lots of greenery, and a pleasant “slow road” vibe.

Route (from north to south)
Stia – Poppi – Bibbiena – Arezzo

Quick Facts

  • Road Number: SR71
  • Reasons to visit: castles, ancient borghi, nature walks

A fun stop (with kids)
In Poppi, you’ll find the Parco Zoo della Fauna Europea: a large, green park featuring European wildlife along a walking trail through the woods.
(And yes: it’s especially nice on hot days, because you walk mostly in the shade.)

Accommodation Tip for Casentino: Hotel Novanta 90

4. Maremma & Monte Argentario: The Rugged Coastal Route

Want to enjoy the sea, scenic viewpoints, and a more rugged side of Tuscany? Then the Maremma is the route for you.

Route (Coast & Lagoon)

  • SS1 Via Aurelia (along the Costa d’Argento)
  • SP161 around Orbetello (for the views)

Highlights

  • Talamone (fishing village + ocean view)
  • Magliano in Toscana (city walls)
  • Alberese (gateway to Parco della Maremma)

Art Stop (check opening hours in advance)
Il Giardino dei Tarocchi (Niki de Saint Phalle) is open from April 1 through October 15, according to the official website.

Accommodation Tip for the Maremma: Tenuta Il Cicalino (especially for mountain bikers and cycling enthusiasts)

5. Monte Amiata: winding roads, forests, and villages (wonderful during the shoulder seasons)

Monte Amiata is a great place to go if you want to escape the summer crowds: higher elevation, forests, local villages, and scenic driving routes.

That’s how I like to visit it best
Combine Amiata with Val d’Orcia or Maremma: 2 nights in the “hills” and 2 nights in the “forests/mountains” for the perfect mix.

6. Garfagnana & Alpe Apuane (near Lucca): marble mountains, bridges, and hidden villages

A completely different side of Tuscany: rougher, greener, and much less touristy.

Suggested Itinerary

  • SP13 (from Pian della Fioba to Castelnuovo di Garfagnana) with a stop at Isola Santa
  • Then head toward Carrara via Via Miseglia / Fantiscritti (marble landscape)

Recommended Stops Along the Way

  • Castelnuovo di Garfagnana (historic town)
  • Barga (colorful, beautiful cathedral)
  • Monte Forato (natural rock arch)

Accommodation Tip for Garfagnana: Agriturismo Braccicorti

Bonus: Elba itinerary (if you want both Tuscany and that island vibe)

Elba is perfect for an extra week (or as a finale): coastal roads, coves, and scenic viewpoints. Read more about it here a beautiful 3-day hiking trip on Elba.

Route (roughly)
Portoferraio – Procchio – Marciana Marina – Sant’Andrea – Fetovaia/Cavoli – Marina di Campo – Lacona – Porto Azzurro – Capoliveri – back

Insider’s tip for a place to stay on Elba: Tenuta delle Ripalte

Practical Tips for Your Road Trip Through Tuscany

  • Florence? Take the train and pick up your car afterward (it saves you stress and the hassle of parking).
  • Driving Time: Plan routes based on driving time and a “stop buffer” (because you’ll need it).
  • Best time to visit: April–June and September–November (nice weather, fewer crowds).
  • Slow travel tip: Many agriturismos require a minimum stay during peak season, so staying at 1–2 fixed locations often works better than changing accommodations every night.
  • Here you’ll find more information about Tuscany, current museum exhibitions and much more.

Sustainable travel

  • Stay at 1 or 2 places during your road trip. Ideally, you should choose 2 locations, for example, so that you can explore an entire province in Tuscany from a single base.
  • Want to explore Tuscany by bike? Read our tips and the most beautiful bike routes through Tuscany here.
  • Check out our tips here for sustainable nature stays and accommodations in Tuscany.
  • If you ‘re driving an electric car to Tuscany, check here for the best tips.

The Most Beautiful Driving Routes in Tuscany on a Map

Madelon Seignette - author

About the author

Madelon Seignette

With a passion for travel and photography and over 30 years of experience in the travel industry, I love to share my special nature travel tips. Travel is wonderful and important, you meet new people and cultures and it opens your view of the world.

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