Day Trips from Arezzo: Val d'Orcia, Cortona & the Best of Southern Tuscany

Arezzo sits at the intersection of four Tuscan provinces and within easy reach of Umbria — a position that makes it one of the best bases in central Italy for day trips. Cortona, Montepulciano, and the Val d’Orcia landscape are all within 90 minutes. Siena and Perugia are under 2 hours.

Cortona (30 km south, approximately 55 minutes by bus)

The most accessible hilltop town from Arezzo. Cortona is a genuine medieval city built on the side of a steep hill with views south across the flat Valdichiana plain to Lake Trasimeno and the Umbrian hills beyond. The Museo dell’Accademia Etrusca e della Città di Cortona (MAEC, Piazza Signorelli 9 — entry approximately €12 as of 2026) has the finest Etruscan collection in the region plus works by Luca Signorelli, the local painter who later influenced Michelangelo. The Santuario di Santa Margherita above the town walls has broad views and a Gothic church with the uncorrupted body of the 13th-century saint displayed in a glass reliquary.

The streets between Piazza della Repubblica and Piazza Signorelli are compact and steep — trainers or flat shoes recommended. The Osteria del Teatro (Via Maffei 2) is among the best restaurants in the area — full dinner from approximately €35–45 per person as of 2026, booking essential.

Getting there: LFI bus from Arezzo bus station to Cortona (Piazza Garibaldi at the base of the hill) — approximately 55 minutes, approximately €3–4 as of 2026. Or Trenitalia regional train from Arezzo to Camucia-Cortona (approximately 20 minutes, approximately €3), then local bus or taxi up to the hilltop (approximately 10 minutes).

Montepulciano (55 km southwest, approximately 1 hour 30 minutes)

Italy’s finest Renaissance hilltop wine town. The main street — Corso — climbs steeply from Porta al Prato to the summit Piazza Grande, passing a sequence of Renaissance palaces, wine cellars carved into the tufa beneath the streets, and the occasional view that stops you mid-step. The Palazzo Comunale tower is climbable for views of the Valdichiana and Val d’Orcia (entry approximately €3 as of 2026).

The wine: Vino Nobile di Montepulciano DOCG is one of Tuscany’s top reds, made from Sangiovese (called Prugnolo Gentile locally). Dozens of producers have cellars open for tastings directly beneath the town streets. Cantina Contucci (Piazza Grande 13 — the oldest noble cellar in the town) offers tastings from approximately €10 per person.

Getting there: From Arezzo by public transport requires a combination — Trenitalia regional train south to Chiusi-Chianciano Terme (approximately 50 minutes, approximately €7), then Tiemme bus to Montepulciano (approximately 30 minutes, approximately €2.50). Times are coordinated — check siautolinee.it. By car, approximately 55 minutes via the SS326.

Pienza and Val d’Orcia (70 km southwest, approximately 2 hours)

Pienza is the “ideal Renaissance city” — the entire town centre is UNESCO-listed and was designed from scratch in the 1460s on the orders of Pope Pius II. It is very small (walkable in 30 minutes), extremely photogenic, and produces the local Pecorino di Pienza cheese (aged and fresh versions — try any of the alimentari shops on Corso Rossellino). The Duomo and Palazzo Piccolomini (entry approximately €7 as of 2026) form the core of the Renaissance plan.

The surrounding Val d’Orcia landscape — soft clay hills (biancane), isolated farmhouses, and the cypress-lined road at Monticchiello — is the most photographed rural landscape in Italy. The best light is early morning or late afternoon. The road between Pienza and San Quirico d’Orcia is where most of the classic images are taken.

Getting there: A car is strongly recommended. From Arezzo, approximately 1.5–2 hours via Montepulciano or directly via the SS326 and SP18. Organised Val d’Orcia tours from Arezzo (from approximately €45–55 per person as of 2026) cover Pienza and Montepulciano with wine tastings included.

Siena (60 km west, approximately 1 hour 20 minutes)

The finest medieval city in Tuscany. The Piazza del Campo is one of Europe’s great public spaces — a sloped shell-shaped piazza where the Palio horse race runs twice yearly (2 July and 16 August). The Duomo interior contains a marble floor with 56 inlaid panels (fully uncovered August–October, entry approximately €15 to see the full floor as of 2026). The Pinacoteca Nazionale (Via San Pietro 29 — entry approximately €8) holds Gothic paintings by Duccio, Simone Martini, and the Lorenzetti brothers.

Getting there: SITA/Autolinee Toscane bus from Arezzo — approximately 1 hour 20 minutes, approximately €8 as of 2026. Alternatively, Trenitalia train (approximately 1.5 hours via Chiusi or Empoli). The bus is usually faster and more direct.

Sansepolcro (45 km northeast, approximately 45 minutes by bus)

Sansepolcro is Piero della Francesca’s birthplace — a quiet market town with one of the greatest paintings of the Renaissance on its wall. The Museo Civico (Via Aggiunti 65 — entry approximately €10 as of 2026) holds Piero’s Resurrection, which Aldous Huxley called “the best picture in the world.” The face of the sleeping soldier in the foreground is traditionally identified as a self-portrait. The Polittico della Misericordia in the same museum is an earlier work by the same hand. The town has almost no tourist crowds — you can stand in front of the Resurrection alone.

Getting there: LFI bus from Arezzo to Sansepolcro — approximately 45 minutes, approximately €4 as of 2026. About 8 services per day.

Perugia (75 km southeast, approximately 1 hour 30 minutes by bus)

Umbria’s capital, a university city on a hilltop with a compact and walkable historic centre. The Galleria Nazionale dell’Umbria (Corso Vannucci 19 — entry approximately €8 as of 2026) has the finest collection of Umbrian painting in the country, with works by Perugino (Raphael’s teacher) and Pinturicchio. The Fontana Maggiore (1278) in the main piazza is the most important medieval fountain in Italy. The Museo Archeologico Nazionale dell’Umbria (entry approximately €8) has outstanding Etruscan and Roman collections.

Perugia is a university city — the food scene reflects this. Sandri (Corso Vannucci 32, pastries from approximately €2–3) is one of the oldest pasticcerie in central Italy. Ristorante Il Cantinone (Via Ritorta 6, pasta approximately €12–14) is reliable for local cuisine.

Getting there: SULGA or APM bus from Arezzo — approximately 1.5 hours, approximately €9 as of 2026. Check sulga.it for timetables.

Practical notes

• The LFI (Lazzi/Ferrovie Italiane) bus network covers most of the Arezzo province destinations; buy tickets at the bus station or online at lfi.it
• Car hire from Arezzo significantly expands your options — Val d’Orcia and the more rural wine estates require a vehicle
• Siena’s historic centre is a ZTL (restricted traffic zone) — if driving, park outside the walls at one of the signed car parks (Piazza del Sale, Santa Caterina) and walk in
• For organised guided day tours from Arezzo (wine, Val d’Orcia, truffle hunting), check GetYourGuide or the Arezzo tourist office at Piazza della Repubblica 28
• Prices listed are approximate as of 2026

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Back to the full Arezzo travel guide for Piero della Francesca, the Piazza Grande, and train connections. For things to do in Arezzo — the Legend of the True Cross frescoes and the antiques market — see things to do in Arezzo. For Arezzo food and restaurants, see the Arezzo food guide. For accommodation, see best hotels in Arezzo. Arezzo sits on the Tuscany itinerary circuit — Florence, Siena, Arezzo, and the Val d’Orcia.