Tuscany Road Trip: 6 Days of Hill Towns from Florence

il Mercato Centrale Firenze

Lively food hall for a proper Tuscan breakfast before hitting the road.

💡 Go before 10am to beat the tour groups.

Piazza del Mercato Centrale, Firenze

Cathedral of Santa Maria del Fiore

Brunelleschi's dome is one of the great engineering feats of the Renaissance and the symbol of Florence.

💡 Book the dome climb online days ahead — it sells out and has timed slots.

Piazza del Duomo, Firenze

Piazza Della Cisterna

Medieval towered skyline that gave the town its 'Manhattan of Tuscany' nickname.

💡 Climb Torre Grossa for the best panoramic view of the towers and countryside.

San Gimignano

Osteria Delle Catene

Trusted local osteria in San Gimignano serving Tuscan classics and the town's own Vernaccia wine, timed perfectly for lunch.

💡 Reserve ahead for a window table overlooking the countryside.

Via Mainardi, 18, San Gimignano

Gelateria Dondoli

Multiple-award-winning gelato shop right on the main piazza, a local institution — perfect after-lunch treat.

💡 Try the Crema di Santa Fina flavor, their signature.

Piazza Della Cisterna, 4, San Gimignano

Piazza del Campo

One of Europe's greatest medieval squares, shell-shaped and ringed by palazzi — the heart of Siena.

💡 Sit at a café terrace in the late afternoon light for the best view of the Torre del Mangia.

Il Campo, Siena

Siena Cathedral

Extraordinary striped marble facade and interior, one of Italy's finest Gothic cathedrals.

💡 Buy the OPA SiPass online to skip ticket lines and access the crypt and baptistery.

Piazza del Duomo, 8, Siena

Pasticceria Nannini Conca D'Oro

Historic Sienese bakery famous for panforte, a dense spiced Tuscan Christmas cake eaten year-round — a quick morning coffee stop before the drive.

Via Banchi di Sopra, 24, Siena

Val d'Orcia Panoramic Viewpoint (San Quirico - Pienza)

UNESCO-listed rolling hills, cypress-lined roads, and farmhouses — the postcard Tuscan landscape.

💡 Stop at the cypress grove viewpoint just south of town for the classic photo.

3MF2+V9, Pienza

Palazzo Piccolomini, Pienza

Ideal Renaissance town, redesigned in the 1450s as a papal utopia — compact and beautifully preserved.

Piazza Pio II, 2, Pienza

Trattoria Latte di Luna

Beloved trattoria just inside Pienza's walls serving hearty Tuscan classics and local pecorino dishes.

💡 Arrive by 12:30 or book ahead — it's tiny and popular with day-trippers.

Via S. Carlo, 2/4, Pienza

Fortezza di Montalcino

14th-century fortress with wine bar inside and walkable ramparts overlooking the vineyards.

💡 Climb the ramparts near sunset for sweeping views over Brunello vineyards.

Piazzale Fortezza, 9, Montalcino

Brunello Di Montalcino Wine Tours & Wine Tastings

Montalcino is the birthplace of Brunello, one of Italy's most prestigious wines.

💡 Book a tasting at a family estate like Col d'Orcia or Tenuta Silvio Nardi ahead of time.

Via IV Novembre, 295, Monteroni d'Arbia

Osteria di Porta al Cassero

Cozy spot for a Tuscan dinner paired with local Brunello and Rosso di Montalcino.

Via Ricasoli, 32, Viale della Libertà, 9, Montalcino

Piazza Grande

Hilltop Renaissance square, setting for parts of the Twilight Saga films, with sweeping valley views.

💡 Climb the Torre di Palazzo Comunale for a 360° view over Tuscany and Umbria.

Montepulciano

Contucci

Historic underground cellars beneath a Renaissance palazzo, home of Vino Nobile di Montepulciano.

💡 Ask for a tasting of Vino Nobile — it's a distinct, food-friendly Sangiovese-based wine.

Via del Teatro, 1, Montepulciano

OSTERIA ACQUACHETA BISTECCA FIORENTINA ALLA BRACE APERTA PRANZO E CENA NO MARTEDI e MERCOLEDÌ, BUONA VITA A TUTTI ‼️

Famous for enormous, perfectly cooked bistecca alla fiorentina grilled tableside.

💡 Reserve well ahead — it's tiny and extremely popular for its steak.

Via del Teatro, 22, Montepulciano

Cortona Centro Storico

Steep Etruscan-Roman hill town made famous by 'Under the Tuscan Sun', with terrific views over Lake Trasimeno.

💡 Walk up to the Fortezza del Girifalco for the best sunset view.

Via Coppi, 3, Cortona

Piazza Grande

Sloping medieval square famous as a filming location for 'Life Is Beautiful', ringed with Gothic and Renaissance buildings.

💡 If visiting on the first weekend of the month, catch the antiques fair filling the square.

Arezzo

Basilica di San Francesco

Home to Piero della Francesca's fresco cycle 'The Legend of the True Cross', a Renaissance masterpiece.

💡 Timed-entry tickets are required to see the frescoes — book online in advance.

Piazza S. Francesco, Arezzo

Ristorante La Lancia D'Oro Arezzo

Elegant osteria on Piazza Grande serving refined Tuscan classics with local Chianti wines.

Piazza Grande, 18, Arezzo

Casa Vasari

Home and self-decorated frescoes of Giorgio Vasari, Renaissance painter and pioneering art historian.

Via XX Settembre, 55, Arezzo

Val di Chiana

Gentle farmland valley between Arezzo and Cortona, famous for the prized Chianina cattle breed.

Foiano della Chiana

Piazza Giacomo Matteotti

Triangular arcaded square at the heart of the Chianti wine region, lively and full of enoteche.

Greve in Chianti

Antica Macelleria Falorni

Legendary Tuscan butcher and deli since 1729, famous for cured meats and finocchiona salami.

💡 Grab a quick lunch plate here around midday before heading out to the castle.

Piazza Giacomo Matteotti, 71, Greve in Chianti

Castello di Verrazzano

Historic castle estate producing Chianti Classico, birthplace of explorer Giovanni da Verrazzano.

💡 Book the cellar tour and tasting in advance — it includes their own balsamic and olive oil too.

Via Castello di Verrazzano, 1, Greve in Chianti

Casa Chianti Classico

Charming stone hill town at the heart of the Chianti Classico zone, with panoramic ramparts walk.

Circonvallazione Santa Maria, 18, Radda in Chianti

Osteria Le Panzanelle

Rustic countryside osteria near Greve serving Tuscan comfort food paired with local Chianti Classico.

💡 Reserve ahead for dinner — it's small and popular with wine-touring visitors in the evening.

Località Lucarelli, 29, Radda in Chianti

Basilica di Santa Maria all'Impruneta

Small but historic town famous for terracotta production and a Renaissance basilica with Michelozzo-designed tabernacles.

Piazza Buondelmonti, 28, Impruneta

Trattoria L'antico forno

A last relaxed countryside lunch before returning to the city.

💡 Aim to sit down by 12:30-13:00 so lunch fits comfortably before the early-afternoon closing.

Via Chiantigiana per Ferrone, 205, Il Ferrone

Oltrarno

Florence's artisan quarter, full of workshops, quieter streets, and the Pitti Palace.

Oltrarno, Florence

Piazzale Michelangelo

Iconic panoramic terrace overlooking the whole city of Florence and the Arno valley — a fitting farewell view.

💡 Arrive an hour before sunset for the best light and to grab a good spot on the steps.

Piazzale Michelangelo, Firenze