5-day loop

La ToscanaThe Painted Hills.

Every Renaissance painter used it as backdrop — the rolling hills of cypress and olive, the white gravel roads (strade bianche) dissolving into the heat haze, the hilltop towers of San Gimignano, the exact curve of the Val d'Orcia valley that every Madonna thereafter repeated. The food is the best in Italy. The wine (Chianti, Brunello, Vino Nobile, Vernaccia) is the most misunderstood. The landscape is UNESCO. Drive slowly. Stop on every hill. April and October are when it all turns gold.

5
Days
~320
km loop
IT
UNESCO x2
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Phrases
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Arrival — Florence & the Chianti Road South
Florence SMN
SR222 Chiantigiana
Greve in Chianti
Siena · 90 min
Fly into Florence (FLR or Pisa PSA) and collect the hire car — you need it for every day of this route. Take the SR222 Via Chiantigiana south rather than the autostrada. The scenic wine road through the Chianti Classico heartland is the first thing you should see, not a motorway.

Chianti & Siena Arrival

5 stops
Morning — The Chiantigiana
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Via Chiantigiana — The Wine Road Through Chianti Classico
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🚗 SR222 · Florence to Siena · 86km · Allow 3–4 hours with stops
The SR222 Via Chiantigiana is the original road connecting Florence and Siena through the Chianti Classico DOCG wine zone — 86km of vineyards, olive groves, cypress avenues, stone farmhouses and hilltop villages in pietra serena. The Chianti Classico zone between Greve in Chianti and Castellina in Chianti is where Sangiovese on galestro soil produces the wine most associated with Tuscany. Stop at Panzano in Chianti for Dario Cecchini. Stop at every agriturismo with wine tasting signs.
⭐86km wine road · Chianti Classico heartland · Cypress avenues · Do not take the autostrada
🍽Solociccia (Panzano, Dario Cecchini, the most theatrical lunch in Tuscany, book ahead at dariocecchini.com)
86km wine road · Chianti Classico · Cypress avenues · No autostrada
Wiki
🥩
Dario Cecchini — The World's Most Famous Butcher
Panzano in Chianti
· Since 1806 ·
Dante at the counter
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📍 Via XX Luglio 11 · Panzano in Chianti · Book Solociccia ahead
Dario Cecchini's macelleria in Panzano has operated at the same address since 1806 — he is the eighth generation. He is the most famous butcher in the world, known for reciting Dante while slicing Chianina beef. His Solociccia restaurant serves a fixed all-meat menu at communal tables — three preparations of Chianina beef, Tuscan bread, estate olive oil and wine, no choices, €30. The queue for the butcher shop and the need to book Solociccia weeks ahead are both indicators of quality.
⭐8th generation since 1806 · Dante while slicing · Solociccia €30 fixed menu · Book weeks ahead
🕘Butcher: Mon–Sat 09:00–19:00 · Solociccia lunch daily · Book at dariocecchini.com
World's most famous butcher · 8th generation · Dante · Solociccia €30
🎟 Book
Afternoon & Evening — Siena
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Siena — The City the Plague Preserved
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📍 Piazza del Campo · Il Palio · UNESCO · Pedestrian centre
Siena is the most intact medieval city in Italy — preserved in its 14th-century state because the Black Death of 1348 killed 50–70% of the population and halted the development that would have erased its medieval fabric. The Piazza del Campo is the finest medieval public square in Italy; the Palazzo Pubblico with the Torre del Mangia (88m) defines its southern edge. Il Palio — held 2 July and 16 August — is the most ferocious civic horse race in Europe, contested between the 17 contrade with a ferocity that includes bribing rival jockeys. The jockey does not need to finish: the horse alone suffices.
⭐Most intact medieval Italy · Piazza del Campo · Il Palio · Torre del Mangia · UNESCO · Free to walk
🕘City always free · Torre del Mangia €10 · Museo Civico €10 · Park outside ZTL at Stadio Comunale
🍽Osteria Le Logge (Banchi di Sopra 33, best in Siena, book ahead) · La Taverna di San Giuseppe (pici cacio e pepe)
Most intact medieval Italy · Plague preserved it · Piazza del Campo · Il Palio · Free
Wiki
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Overnight: Siena
🛏 Base for 2 nights
🏨Palazzo Ravizza (historic palazzo, garden) · Grand Hotel Continental (Banchi di Sopra, grand)
💡Park outside the ZTL at Parcheggio Santa Caterina or the Stadio. Everything in Siena is on foot.
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San Gimignano & Siena Duomo
Siena
San Gimignano · 40 min
Return to Siena · afternoon
A morning at San Gimignano — arrive before 09:30 to beat the coach tours — then back to Siena for the Duomo and the Pinacoteca. The two cities together make a perfect day of medieval Tuscany without driving more than 40 minutes each way.

San Gimignano & Siena Deep

6 stops
Morning — San Gimignano
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San Gimignano — The Manhattan of the Middle Ages
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📍 Province of Siena · 14 surviving towers of 72 · UNESCO · Vernaccia wine
San Gimignano has 14 medieval towers still standing of an original 72 — built by rival merchant families in the 13th century as expressions of wealth and status on the Via Francigena pilgrimage route. The silhouette visible from the valley floor is one of the most recognisable in Italy. The town produces Vernaccia di San Gimignano — the first Italian wine to receive DOC designation (1966). Gelateria Dondoli on Piazza della Cisterna has won the World Gelato Championship twice and is the correct stop before leaving.
⭐14 towers of 72 · Rival merchant families · Vernaccia DOC · UNESCO · Arrive before 09:30
🕘Town always free · Torre Grossa €9 · Gelateria Dondoli: daily · Coach tours 10:00–16:00 — avoid
🍽Gelateria Dondoli (Piazza della Cisterna 4, twice World Gelato Champion — Crema di Santa Fina: saffron and pine nut)
14 towers of 72 · Manhattan of Middle Ages · UNESCO · Arrive early · Dondoli gelato
Wiki
Afternoon — Siena Cathedral & Art
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Duomo di Siena — The 56-Panel Marble Floor
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📍 Piazza del Duomo · Most richly decorated Gothic church Italy · €8
The Siena Cathedral is the most richly decorated Gothic church in Italy — built in black and white marble banding. The defining element is the marble floor: 56 inlaid panels executed between 1369 and 1547 by generations of Sienese artists including Pinturicchio and Beccafumi. The full floor is visible (uncovered) from late August to late October only — the finest months to visit. The Libreria Piccolomini (frescoed by Pinturicchio 1502–1508) is an explosion of colour disproportionate to the room's small size.
⭐56-panel marble floor · Full floor visible late Aug–Oct · Libreria Piccolomini · €8
🕘Mon–Sat 10:30–19:00 · Sun 13:30–18:00 · €8 · OPA SI Pass available for multiple sites
56-panel marble floor · Most richly decorated Gothic Italy · Pinturicchio · €8
Wiki🎟 Book
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Pinacoteca Nazionale di Siena — The Sienese School
Duccio · Simone Martini · €4 · Usually empty
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📍 Via San Pietro 29 · The parallel tradition to Florence · €4
The finest collection of Sienese school painting in the world — the tradition of Duccio, Simone Martini and the Lorenzetti brothers that ran parallel to, and in competition with, the Florentine school. The Sienese maintained a closer connection to the Byzantine gold-ground tradition, emphasising emotional intensity and linear elegance. This makes it more beautiful and less famous than it deserves. Entry costs €4 and the rooms are almost always empty.
⭐Duccio · Simone Martini · Lorenzetti · €4 · Finest Sienese school · Usually empty
🕘Mon 09:00–13:30 · Tue–Sat 09:00–18:00 · Sun 09:00–13:00 · €4 · Allow 1.5 hours
Finest Sienese school · Duccio · Simone Martini · €4 · Almost empty
Wiki
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Val d'Orcia — The UNESCO Landscape
Siena
Montalcino · 40 min
SP146 strade bianche
Pienza · 10 min
Montepulciano · 30 min
The day the landscape becomes the destination. The Val d'Orcia is a UNESCO Cultural Landscape — the rolling clay hills, cypress allees and lone farmhouses that Renaissance painters used as sacred backgrounds. Move base to Montepulciano tonight.

Val d'Orcia UNESCO

7 stops
Morning — Montalcino & Brunello
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Montalcino — Home of Brunello, Italy's Greatest Red Wine
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📍 Fortezza Medicea · Brunello DOCG · 5-year minimum ageing
Montalcino sits above the Val d'Orcia, its vineyards producing Brunello di Montalcino — widely considered Italy's finest red wine. Made exclusively from Sangiovese Grosso (locally called Brunello), aged minimum 5 years before release, Brunello is capable of ageing 20–50 years. The Fortezza Medicea at the summit contains an enoteca where you can taste wines from multiple producers by the glass (€4–12). Do this before buying at an estate — understand the style first.
⭐Italy's greatest red wine · Brunello DOCG · 5yr minimum · Fortezza enoteca · Taste before buying
🕘Fortezza enoteca: daily 09:00–20:00 · Tasting by glass €4–12 · Town always free
🍽Il Leccio (Sant'Angelo in Colle, Michelin, exceptional Brunello list, book far ahead)
Italy's greatest red · Brunello DOCG · 5yr minimum · Fortezza enoteca
Wiki
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The Strade Bianche — Driving the White Gravel Roads
SP146 · Cypress allees · Inside the painting · Free
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🚗 SP146 San Quirico d'Orcia to Pienza · The most photographed road in Tuscany
The strade bianche (white roads) are unpaved gravel and clay tracks whose pale surface against the brown clay landscape is the defining visual element of Tuscan photography. The SP146 from San Quirico d'Orcia to Pienza is the most photographed road in Tuscany — turning onto it and driving slowly toward a cypress allee with a case colonica at the end is as close as you can get to living inside a Renaissance painting. Passable in any car in dry weather. In rain, 4WD preferred.
⭐White gravel roads · Cypress allees · Inside the painting · SP146 best section · Always free
🕘Always · Free · Drive SP146 · Stop at every crest · Early morning mist or late afternoon gold light
White gravel roads · Inside the painting · SP146 · Cypress allees · Free
Afternoon — Pienza & the Val d'Orcia
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Pienza — The Ideal Renaissance City
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📍 Val d'Orcia · UNESCO · Pope Pius II 1459 · Pecorino di Pienza
Pienza was rebuilt entirely in 1459 by Pope Pius II as an ideal Renaissance city — the cathedral, papal palace, town hall and bishop's residence grouped around a travertine piazza designed to Alberti's humanist principles. The project was completed in three years. Pienza is also the centre of Pecorino di Pienza production: sheep's milk cheese aged in walnut leaves, clay pots or grape marc. Buy and taste at every shop on the Corso.
⭐Ideal Renaissance city 1459 · Pope Pius II · Travertine piazza · Pecorino di Pienza · UNESCO
🕘Town always free · Cathedral free · Papal Palace €3 · Pecorino: taste before buying at every shop
🍽Trattoria Latte di Luna (Val d'Orcia terrace view, pici with wild boar)
Ideal Renaissance city · Pope Pius II · Travertine piazza · Pecorino · UNESCO Val d'Orcia
Wiki
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The Val d'Orcia — The UNESCO View
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📍 Between Pienza and San Quirico · Best light: early morning or late afternoon
The Val d'Orcia is a UNESCO World Heritage Cultural Landscape — one of the very few landscapes protected specifically for aesthetic and cultural reasons, because it was depicted by Renaissance painters as background for sacred scenes. The rolling crete senesi (clay hills), cypress allees, lone farmhouses on knolls, and the specific quality of Tuscan light have been reproduced so often that the landscape itself has become a cultural object. April (green wheat, red poppies) and October (harvest gold) are the two peak seasons.
⭐UNESCO for aesthetic reasons · Renaissance painting backgrounds · April/Oct best · Free
🕘Always · Free · Drive SP146 · Stop every crest · Early morning mist · Late afternoon gold
UNESCO for aesthetics · Renaissance backgrounds · April/Oct best · Free
Wiki
Evening
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Overnight: Montepulciano
🛏 1 night · Vino Nobile · The most elegant hilltop town
🏨Relais San Bruno (elegant, views) · La Terrazza di Montepulciano (B&B, Val d'Orcia views) · Agriturismi in surrounding hills
🍽Osteria dell'Acquacheta (Via del Teatro 22 — pici pasta, no reservations, queue early, best value Tuscany)
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Montepulciano, Cortona & Arezzo
Montepulciano · morning
Cortona · 30 min
Or Arezzo · 30 min
North toward Florence
Montepulciano for Vino Nobile in the morning, then a choice: Cortona (Fra Angelico, Etruscan bronze, Frances Mayes hilltown) or Arezzo (Piero della Francesca's Legend of the True Cross — the finest fresco cycle in Tuscany, book ahead). End the day at a Chianti agriturismo.

Montepulciano & the East

6 stops
Morning — Montepulciano
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Montepulciano — Vino Nobile & the Piazza Grande
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📍 Piazza Grande · Vino Nobile DOCG · Medieval tufa cellars · Poliziano birthplace
Montepulciano is described by the Renaissance humanist Poliziano (born here in 1454) as the "pearl of all hilltowns." The Corso ascends through Renaissance and Baroque palazzi to the Piazza Grande. The cantinas beneath the palazzi descend into medieval tufa tunnels where Vino Nobile ages. Named "nobile" by papal decree in 1685, made from Prugnolo Gentile (Sangiovese clone), aged minimum 2 years. Cantina Contucci and Cantina del Redi both welcome visitors with free tastings.
⭐Vino Nobile DOCG · Medieval tufa cantinas · Piazza Grande · Free tastings · ZTL: park at Porta al Prato
🕘Town always free · Cantinas daily from 10:00 · Tasting often free · ZTL: park outside
🍽Osteria dell'Acquacheta (no reservations, queue early, the best value lunch in Tuscany)
Vino Nobile DOCG · Medieval cantinas · Piazza Grande · Free tastings
Wiki
Afternoon — Cortona or Arezzo
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Cortona — Fra Angelico & Etruscan Bronze
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📍 Province of Arezzo · Lake Trasimeno below · Fra Angelico · Etruscan collection
Cortona is an Etruscan city of considerable antiquity on a steep hill above Lake Trasimeno — made famous internationally by Frances Mayes's "Under the Tuscan Sun" (1996) but more interesting for the Fra Angelico paintings in the Museo Diocesano and the Etruscan bronze Lampadario in the Museo dell'Accademia Etrusca. Less visited than San Gimignano and considerably more authentic in atmosphere.
⭐Fra Angelico paintings · Etruscan Lampadario bronze · Lake Trasimeno view · Less crowded · €5
🕘Town always free · Museo Diocesano €5 · Etruscan Museum €5 · Allow 2 hours
🍽Trattoria Dardano (Cortona, local, no frills, excellent)
Fra Angelico · Etruscan bronze · Lake Trasimeno · Less crowded
Wiki
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Arezzo — Piero della Francesca's Legend of the True Cross
Finest fresco cycle Tuscany
· Cappella Bacci ·
25 people at a time · €12
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📍 Basilica di San Francesco · Timed entry · Book ahead at pierodellafranesca.it
Piero della Francesca's Legend of the True Cross (1452–1466) in the Cappella Bacci is the finest fresco cycle in Tuscany — 10 scenes painted with Piero's characteristic geometric rigidity, luminous colour, and the specific depicted silence that makes his paintings feel like dreams. Entry is strictly timed (25 visitors, 30 minutes per slot) and must be booked in advance. If you have not booked, try for a same-day slot at the booking office at 08:00.
⭐Finest fresco cycle Tuscany · Piero della Francesca · Timed entry 25 people · Book ahead · €12
🕘Mon–Fri 09:00–18:00 · Sat 09:00–17:00 · Sun 13:00–17:30 · €12 · Book at pierodellafranesca.it
Piero della Francesca · Finest fresco Tuscany · Book ahead · €12 · 25 people max
Wiki🎟 Book
Evening
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Overnight: Chianti Agriturismo
🛏 The ideal final night · Between Siena and Florence
💡Sleep in a renovated Chianti farmhouse. Dinner in the estate kitchen. Breakfast with estate olive oil. This is the Tuscany that exists between the towns — book directly.
🏨Fattoria di Petroio (Gaiole, estate wine) · Castello di Spaltenna (Gaiole, medieval castle, pool)
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Chianti North — The Return to Florence
Chianti agriturismo
Castello di Brolio · 15 min
Badia a Coltibuono · 10 min
Florence · 1h
The final day drives north through the quietest section of Chianti — Gaiole, Brolio, Badia a Coltibuono — before returning to Florence. The two estate stops are brief but the most specifically Chiantigiano of the whole route.

Chianti North & Florence Return

5 stops
Morning — The Estate Road North
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Castello di Brolio — Where Modern Chianti Was Invented
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📍 Gaiole in Chianti · Baron Bettino Ricasoli · Chianti formula 1872
The ancestral home of the Ricasoli family — where Baron Bettino Ricasoli (twice Prime Minister of united Italy) developed the Chianti blend formula in 1872: Sangiovese, Canaiolo and Malvasia in specific proportions that defined Chianti for the next century. The family still lives here (the oldest Florentine noble family with continuous ownership since 1141). The ramparts give the finest panoramic view in the Chianti Classico zone. The estate enoteca sells direct at estate prices.
⭐Chianti formula invented here 1872 · Ricasoli family still live here · Rampart views · Direct wine · €5
🕘Daily 10:00–18:00 · €5 gardens and ramparts · Enoteca free tasting · Book at ricasoli.com
Chianti formula 1872 · Ricasoli family · Rampart panorama · Direct wine · €5
WikiVisit
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Badia a Coltibuono — The Abbey That Makes Wine
11th-century abbey · Wine estate · Best estate lunch Chianti
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📍 Gaiole in Chianti · Founded 1000 AD · Estate restaurant · Book ahead
An 11th-century Vallombrosan monastery secularised in 1810, acquired by the Stucchi Prinetti family in 1846 and converted into one of the finest Chianti Classico estates. The abbey church and cloisters are intact and free to visit. The estate restaurant (lunch only, seasonal, April–October) serves Tuscan food made entirely from estate produce — olive oil, wine, honey, vegetables — in a garden setting that is the most beautiful lunch venue in the Chianti zone. Book at coltibuono.com.
⭐11th-century abbey · Wine estate 1846 · Estate restaurant (best Chianti lunch) · Free abbey visit
🕘Abbey daily · Free · Restaurant lunch Apr–Oct · Book at coltibuono.com · Wine shop daily
11th-century abbey · Best estate lunch Chianti · Estate restaurant · Free to visit
Book Lunch
Afternoon — Florence or Departure
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Florence — If Time Allows Before the Flight
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📍 Uffizi Gallery · Or Mercato Centrale food shopping · 1h from Chianti
If your flight is late afternoon, 3 hours in Florence is achievable. The Uffizi holds the greatest concentration of Renaissance painting in the world — Botticelli's Primavera and Birth of Venus, Leonardo's Annunciation, Titian, Raphael, Caravaggio. Book online at uffizi.it (3+ days ahead) — the queue without a booking destroys the morning. Alternative: Mercato Centrale (San Lorenzo, the covered food market) for final food shopping before flying.
⭐Uffizi: Botticelli · Leonardo · Raphael · €25 · Book at uffizi.it · Or Mercato Centrale food shopping
🕘Uffizi: Tue–Sun 09:00–18:00 · €25 · Book online · Mercato Centrale: daily 07:00–14:00 · Free
🍽Trattoria Mario (Rosso, San Lorenzo, communal tables, classic Florentine lunch, cheap, always busy)
Uffizi · Botticelli · Leonardo · €25 · Book ahead · Or Mercato Centrale food shopping
🎟 Uffizi
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Departure from Tuscany
✈️ Florence · Pisa · Or train from Florence SMN
✈️Florence Peretola (FLR): 15 min from centre · Ryanair, easyJet, Vueling to Europe · Return car at FLR
✈️Pisa Galileo Galilei (PSA): 1h from Florence · More routes · Better if driving from south end of loop
🚄Train: Florence SMN to Rome 1h 30min · Milan 1h 45min · Venice 2h (Frecciarossa)
💡Buy before leaving: Brunello di Montalcino at direct price from the Fortezza, Pecorino di Pienza vacuum-packed, estate olive oil from your agriturismo. None of this is available at this quality outside the region.
Toscana Italian Phrases

Tuscan Italian is the purest form of the language — Dante wrote the Divine Comedy in Florentine Tuscan in the 14th century and established it as the literary standard. The Accademia della Crusca (the academy that defines correct Italian, founded in Florence in 1583) still operates here. Tuscan people are proud of their food, wine and art in a way that is direct without being aggressive. Salute!

Greetings
Good morning
Buongiorno!
bwon-JOR-no
Good morning — always when entering any shop, cantina or restaurant. In Tuscany, especially in Siena and smaller towns, this greeting exchange is still taken seriously.
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Thank you
Grazie mille!
GRA-tsyeh MEE-leh
A thousand thanks — the warmest Italian expression of gratitude. Response: "Prego" (you're welcome) or "Di niente" (nothing at all).
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Wine & the Cantina
May I do a tasting?
Posso fare una degustazione?
POS-so FA-reh OO-na deh-goos-ta-TSYO-neh
May I do a tasting? — the correct request at a Tuscan estate. Ring the gate bell, say Buongiorno and ask this. Most estates in Chianti, Montalcino and Montepulciano welcome visitors; tastings are often free with a purchase.
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A glass of Chianti Classico
Un bicchiere di Chianti Classico, per favore.
un bik-KYEH-reh dee KYAN-tee KLAS-si-ko
A glass of Chianti Classico please — look for the Gallo Nero (Black Rooster) seal on the bottle neck. Ask for a Gran Selezione if available — the finest tier of the appellation.
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I will take six bottles
Ne prendo sei bottiglie.
neh PREN-do SEH-ee bo-TEE-lyeh
I will take six bottles — direct estate prices for Brunello, Vino Nobile and Chianti Gran Selezione are 30-50% below restaurant prices. A mixed case in checked luggage is worth the excess baggage charge.
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Food — The Tuscan Table
The Tuscan pasta
Pici cacio e pepe, per favore.
PEE-chee KA-cho eh PEH-peh
Pici with cheese and pepper please — pici are thick hand-rolled pasta (flour and water, no eggs), the defining pasta of the Siena and Val d'Orcia area. Order this everywhere in the region.
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A Florentine steak
Una bistecca fiorentina, per favore.
OO-na bi-STEK-ka fyo-ren-TEE-na
A Florentine steak please — a T-bone of Chianina beef, minimum 1.2kg, grilled over oak charcoal, served rare. Never well done — Dario Cecchini refuses. Priced by the etto (100g), typically €8-12/etto.
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The bill please
Il conto, per favore.
il KON-to per fa-VO-reh
The bill please — it will not arrive uninvited in Italy. "Coperto" (cover charge, €1.50-3) covers the bread and is separate from tipping. 10% is appreciated in sit-down restaurants.
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Toasts & the Tuscan Character
Cheers!
Salute!
sa-LOO-teh
To health! — the standard Italian toast. Eye contact before drinking. With Brunello: swirl the glass, nose it for 30 seconds before tasting. A wine that took 5 years to mature deserves more than 3 seconds of your attention.
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What a beautiful landscape!
Che bel paesaggio!
keh bel pa-eh-ZAH-jo
What a beautiful landscape! — you will need this constantly in the Val d'Orcia. The cypresses on the ridge are planted by the farmers, not by nature — their presence is a deliberate aesthetic choice maintained for centuries.
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Toilet
Dov'e' il bagno?
do-VEH il BAN-yo
Where is the bathroom? — in restaurants always at the back or downstairs. Many Italian public toilets require a €0.50 coin.
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Copiato!