Frances Mayes wrote about Cortona. Twilight was filmed (sort of) in Montepulciano. Both towns have been significantly shaped by their literary and cinematic associations. The question of which is worth your time doesn't depend on either of these facts. This is the guide that ignores the mythology and looks at what each town actually contains.
Read the guide →Both hill towns sit in the same Tuscan landscape — the Val di Chiana plain between Arezzo and Lake Trasimeno — and both attract visitors for similar reasons: medieval architecture, panoramic views, local wine, and the specific pleasure of a Tuscan hill town that still functions as a real community rather than a museum. But they're different in character, in history, and in what they offer. Choosing between them for a day trip or overnight stay requires understanding what each actually provides.
The comparison became a tourist conversation partly because Frances Mayes's memoir Under the Tuscan Sun (1996) was set in Cortona, generating enormous American interest that transformed the town's visitor composition. Montepulciano has its own literary connection — it appears in Poliziano's (Angelo Ambrogini) 15th-century Latin poetry, and more recently as the setting for the Twilight saga's Volterra scenes (actually filmed in Montepulciano, causing a surge in vampire-related tourism). Neither connection is why you should visit.
Cortona's specific attractions, in honest order of importance:
1. The Etruscan walls and MAEC museum: The Etruscan circuit wall (6th century BC, partially preserved) and the MAEC museum (Piazza Signorelli 9, €12, open 10am–7pm) together constitute one of the most complete Etruscan experiences in central Italy. The bronze Etruscan lamp (5th century BC) in the MAEC is extraordinary. Most visitors to Cortona who come for the Under the Tuscan Sun association skip this completely. Don't.
2. The Annunciation by Beato Angelico: The Diocesan Museum (Museo Diocesano, Piazza del Duomo 1, €8) contains Fra Angelico's Annunciation (1430) and his Madonna Enthroned with Angels — two of the finest early Renaissance works in Tuscany, outside the major museum circuit. Also: Luca Signorelli's altarpieces, from the artist who was born in Cortona and whose Sistine-scale work at Orvieto Cathedral influenced Michelangelo directly.
3. The view from the fortress: The Fortezza Medicea at the top of Cortona (walk from the Piazza della Repubblica, 25 minutes uphill) offers one of the best views in Tuscany — the Val di Chiana flat plain, Lake Trasimeno, and the profile of Monte Cetona visible on clear days. This view explains why the Etruscans chose this site 2,700 years ago.
Montepulciano's specific attractions:
1. Vino Nobile di Montepulciano DOCG: The wine produced from Prugnolo Gentile (a Sangiovese clone) in the hills around Montepulciano was first documented in 789 AD. The DOCG designation was established in 1980, making it Italy's first DOCG red wine. Visiting producers in the cellars beneath the town: Avignonesi (Via di Gracciano nel Corso 91) and Contucci (Palazzo Contucci, Piazza Grande 13 — the historic palace wine cellar open daily for tastings). Wine by the glass €4–8, bottle €15–35 at the cellar.
2. The Renaissance architectural coherence: Montepulciano's main street (Via di Gracciano nel Corso, ascending to Piazza Grande) is a 16th-century Renaissance urban planning exercise — the palaces, churches, and public buildings were designed or redesigned in the Renaissance period when the Florentines controlled the town and wanted to demonstrate their architectural taste. The result is more coherent than most Tuscan towns: a complete Renaissance urban corridor rather than a mix of periods.
3. Piazza Grande and the Cathedral: The Piazza Grande at the top of Montepulciano is one of the finest Renaissance piazze in Italy — a large, formally composed space with the unfinished Palazzo Comunale (town hall with a tower you can climb for €3.50), the Cathedral, and two Medici wells. The Cathedral contains Taddeo di Bartolo's extraordinary altarpiece of the Assumption (1401) and a Michelozzo-designed tomb.
From Florence: Cortona — 100km, 1.5 hours by car or train to Camucia-Cortona station (7km from the old town, taxi €12). Montepulciano — 130km, 1.5 hours by car; no direct train (change at Chiusi-Chianciano Terme, then bus).
From Siena: Montepulciano is 60km (1 hour), significantly closer. Cortona is 80km (1.5 hours).
Combined visit: Both towns are 30km apart and a combined day trip is possible — Cortona morning (MAEC museum, Fra Angelico), Montepulciano afternoon (wine tasting at Contucci, Piazza Grande). This is rushed. Two days covering both towns properly is significantly better.
Accommodation: Cortona has slightly more accommodation options in the historic centre. Montepulciano's surroundings have excellent agriturismo options (several Vino Nobile producers have guest rooms). Cortona accommodation: €80–180 per night for a mid-range option in the old town.
For history (pre-Roman, Etruscan): Cortona wins clearly — the Etruscan walls and MAEC museum have no equivalent at Montepulciano. For wine: Montepulciano wins clearly — Vino Nobile di Montepulciano DOCG is one of Italy's great red wines with cellars open daily in the town centre. For architecture: Montepulciano's Renaissance urban coherence is more architecturally spectacular. For the "classic Tuscan hill town experience": similar — both are genuine, non-museified communities. For accessibility from Florence: Cortona (direct train to Camucia-Cortona). For accessibility from Siena: Montepulciano. The Cortona vs Montepulciano debate resolves differently depending on your primary interest.
Cortona and Montepulciano are approximately 30km apart, a 35–40 minute drive via the SP146 road that passes through the Val di Chiana. There is no direct public transport connection — a day trip visiting both requires a car. From Arezzo (the nearest major city): Cortona is 30km south (30 minutes), Montepulciano is 60km south (1 hour). A combined day trip from Arezzo is feasible. From Siena: Montepulciano is the easier single destination (60km, 1 hour); adding Cortona makes the day long but manageable.
Montepulciano is known for Vino Nobile di Montepulciano DOCG — a red wine made from Prugnolo Gentile (a local clone of Sangiovese), aged a minimum of 2 years (3 for Riserva), with a specific earthy, cherry, and herbal character. It was Italy's first DOCG red wine (1980). The Cortona vs Montepulciano comparison for wine always ends at Montepulciano — Cortona has limited wine production (some Syrah-based wines in recent years, interesting but not comparable to Vino Nobile). For the wine experience, Montepulciano is clearly the better destination. The cellars beneath the town — particularly Contucci and Avignonesi — offer tastings without appointment from €8–12 per flight.
Frances Mayes's memoir Under the Tuscan Sun (1996, filmed 2003 with Diane Lane) transformed Cortona from a medium-visited Tuscan hill town into one of Italy's most recognised American tourist destinations. The effect is measurable: Cortona's international visitor numbers increased dramatically in the late 1990s and early 2000s, accommodation prices rose, and English-language-friendly restaurants appeared throughout the old town. The book and film also created a specific narrative about "buying a ruin in Tuscany" that spawned an entire genre of memoir and a significant expat real estate market in the region. The town itself didn't change structurally — Cortona remains a functioning Italian community with its Etruscan walls, its MAEC museum, and its Fra Angelico Annunciation — but the visitor composition and associated infrastructure shifted significantly. For the Cortona vs Montepulciano comparison, Cortona has more English-language tourist infrastructure; Montepulciano has a more specifically Italian visitor base.
The most efficient day trip combining both towns: Train from Florence to Camucia-Cortona (1.5 hours, €8–12), taxi to Cortona old town (€12), 3 hours in Cortona (MAEC museum, Fra Angelico at the Diocesan Museum, lunch), drive or taxi to Montepulciano (30km, €25 taxi), 2.5 hours in Montepulciano (Piazza Grande, Contucci wine cellar tasting, Cathedral), late afternoon return to Florence via Chiusi train station (20km, taxi €20). This requires a car or taxi connection between the two towns. Total cost: approximately €80–100 per person including transport, museum entries, lunch, and wine tasting. Related: Tuscany wine tour guide, Tuscany travel guide.
Day trips from Florence or Siena, combined itineraries, Vino Nobile tastings, and Etruscan heritage tours across the Val di Chiana.
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