Tuscany
5
Day Itinerary •
Italy
Five days in Tuscany allows you to explore the full extraordinary range of one of the world's most beautiful regions. From Florence's overlooked Renaissance masterpieces to the dawn landscapes of the Val d'Orcia, from Siena's rival medieval neighbourhoods to the Chianti wine hills, from the perfectly intact medieval city of Lucca to the Etruscan city of Volterra on its windswept ridge. This route covers the complete hidden Tuscany. Florence's secret courtyards and forgotten frescoes, the UNESCO Val d'Orcia landscape at golden hour, Siena's extraordinary contrade culture, the Chianti wine road through cypress-lined valleys, San Gimignano's medieval towers at dawn before the day-trippers, and the Etruscan heritage of Volterra that predates even Rome.
Best Time To Visit
April to June or September to October
Getting There
Fly into Florence (FLR) or Pisa (PSA)
Getting Around
Rental car essential throughout
Budget Per Day
Approx 100 to 160 euros per person per day
Difficulity
Easy, walking and driving
DAY 1
FLORENCE HIDDEN GEMS
MORNING
FLORENCE'S OVERLOOKED MASTERPIECES
The Cappella Brancacci contains Masaccio's frescoes that taught Michelangelo how to paint. The Museo dell'Opera del Duomo has the original Gates of Paradise and Michelangelo's unfinished Pieta with almost no queues. The Chiostro dello Scalzo has extraordinary free Andrea del Sarto frescoes. All three are within 30 minutes walk and collectively better than most of what the Uffizi contains. Drive: 15 min walk to Oltrarno
MIDDAY
OLTRARNO, THE FLORENCE MOST VISITORS MISS
Cross the Ponte Vecchio into the Oltrarno neighbourhood where Florentines actually live. The Piazza Santo Spirito is the finest square for authentic local life. The Basilica di Santo Spirito has a remarkable Brunelleschi interior almost always empty. The Boboli Gardens behind the Pitti Palace contain extraordinary hidden corners most visitors never find. Drive: 15 min walk to San Miniato
AFTERNOON
SAN MINIATO AL MONTE, VESPERS AT SUNSET
The most beautiful Romanesque church in Tuscany, built in 1013 on a hilltop above the city. The Benedictine monks still chant Vespers at 5:30pm and the sound in the medieval interior is unforgettable. Stay for sunset over Florence from the hilltop terrace afterwards.
💎 HIDDEN GEM
The Corridoio Vasariano, the secret elevated corridor built by Cosimo I de Medici in 1565, runs above the Ponte Vecchio for nearly a kilometre. Currently undergoing restoration but portions are sometimes accessible. The corridor contains hundreds of self-portraits from the Uffizi collection displayed in an extraordinary private passage.
🍽 WHERE TO EAT
Breakfast: Caffe Rivoire, Piazza della Signoria Most beautiful cafe terrace in Florence. Strong espresso overlooking the piazza. | Lunch: Trattoria Sostanza, Florence Oldest trattoria in Florence, opened 1869. The butter pasta is legendary. Book ahead. | Dinner: Buca Mario, Florence Oldest restaurant in Florence, founded 1886. Traditional Florentine cuisine in a beautiful historic cellar.
DAY 2
VAL D'ORCIA
MORNING
MIDDAY
PIENZA, THE IDEAL RENAISSANCE CITY
Pope Pius II had his entire birthplace village rebuilt in 1459 as the first ideal Renaissance city. An extraordinary cathedral, episcopal palace and town hall around a perfect trapezoidal piazza. Buy Pecorino di Pienza directly from producers in the main street. Drive: 20 min drive to Montalcino
AFTERNOON
MONTALCINO AND BAGNO VIGNONI
The home of Brunello di Montalcino. The 14th-century fortress still functions as a wine bar within its ancient walls. Then drive to Bagno Vignoni, where the main square is a thermal pool built by the Medici, still steaming with hot spring water. Lorenzo de Medici and Saint Catherine of Siena both bathed here.
💎 HIDDEN GEM
The Abbazia di Sant'Antimo near Montalcino stands alone in a valley surrounded by olive groves. Gregorian chant is sung at 7am, 12:45pm and 7pm. The 7pm service in the 12th-century church is the most moving experience in Tuscany. Free entry.
🍽 WHERE TO EAT
Breakfast: Bar in San Quirico d'Orcia Leave by 6:30am. Coffee after the sunrise shoot. | Lunch: Trattoria Latte di Luna, Pienza Most beloved restaurant in Pienza. Local pici pasta and finest Pecorino. Book ahead. | Dinner: Osteria di Porta al Cassero, Montalcino Traditional Sienese cuisine. Local cinghiale ragu and Brunello at honest prices.
DAY 3
SIENA AND CRETE SENESI
MORNING
SIENA BEYOND THE PIAZZA DEL CAMPO
Siena's 17 contrade are ancient medieval neighbourhoods that still function as rival city-states. Walk the Terzo di San Martino, Terzo di Citta and Terzo di Camollia to find the neighbourhood museums, each containing extraordinary art and Palio horse race silks. Most are free. Drive: 15 min walk to Duomo
MIDDAY
THE LIBRERIA PICCOLOMINI
Inside the Siena Duomo, the Libreria Piccolomini was painted entirely by Pinturicchio in 1502 with 10 extraordinary frescoes. Far less crowded than the main cathedral. The Palazzo Pubblico contains Simone Martini's Maesta and Lorenzetti's Allegory of Good and Bad Government. Entry approx 9 euros. Drive: 30 min drive to Crete Senesi
AFTERNOON
CRETE SENESI AND SAN GALGANO
The extraordinary lunar clay landscape south of Siena, bare rolling hills in grey and ochre. Drive the road between Asciano and Buonconvento at golden hour. Then visit the Abbazia di San Galgano, a Gothic abbey whose roof collapsed centuries ago, leaving an extraordinary skeleton of stone arches open to the sky.
💎 HIDDEN GEM
The Palazzo Pubblico Sala del Mappamondo contains the finest surviving example of secular medieval painting in Italy. Simone Martini's 1315 Maesta and Lorenzetti's extraordinary Allegory of Good and Bad Government. Entry approx 9 euros and far less crowded than the Uffizi.
🍽 WHERE TO EAT
Breakfast: Caffe Fiorella, Siena Finest coffee in Siena near the Piazza del Campo. Local ricciarelli almond cookies. | Lunch: Osteria Le Logge, Siena Most celebrated traditional restaurant in Siena. Pici al ragu and the finest Chianti Classico. | Dinner: Trattoria Papei, Siena Beloved neighbourhood trattoria. Generous portions, honest prices and excellent local wine.
DAY 4
CHIANTI AND SAN GIMIGNANO
MORNING
SAN GIMIGNANO, THE MEDIEVAL MANHATTAN AT DAWN
San Gimignano is one of the most extraordinary medieval townscapes in the world, its 14 surviving towers rising dramatically above the Chianti hills. Visited by millions but almost always in the afternoon. Arrive before 8am and walk the empty tower streets in complete solitude. The Collegiata church contains extraordinary 14th-century fresco cycles of the Old and New Testament covering every inch of the interior walls. Entry approx 6 euros. Drive: 30 min drive to Chianti
MIDDAY
THE CHIANTI WINE ROAD
The strada del vino between Greve in Chianti and Radda is one of the most beautiful wine drives in Europe, winding through cypress-lined hills, medieval castles and villages completely unchanged since the 15th century. Greve in Chianti has an extraordinary triangular main piazza and the finest butcher in Tuscany, Macelleria Falorni, which has been curing meat since 1729. Buy finocchiona salami and lardo di Colonnata. Drive: 25 min drive to Castello di Brolio
AFTERNOON
CASTELLO DI BROLIO, THE BIRTHPLACE OF CHIANTI CLASSICO
The Barone Ricasoli estate at Castello di Brolio is where Bettino Ricasoli invented the Chianti Classico blend in 1872. The castle on its hilltop has extraordinary views over the Chianti landscape. The enoteca offers tastings of the current releases from approx 10 euros. The castle gardens and towers can be visited independently. One of the finest hilltop landscapes in all of Tuscany.
💎 HIDDEN GEM
The village of Volpaia, perched on a high hill in the Chianti between Radda and Gaiole, is one of the finest and most overlooked medieval villages in Tuscany. An extraordinary fortified village with intact walls, an ancient church, a single wine bar and almost no tourists despite being one of the most beautiful villages in Italy.
🍽 WHERE TO EAT
Breakfast: Bar in San Gimignano at dawn The village has several cafes that open early. Coffee and a cornetto before the towers empty again. | Lunch: Macelleria Falorni deli, Greve Buy cured meats, local cheese and Chianti Classico for a picnic in the vineyard. The finest Tuscan picnic possible. | Dinner: Osteria di Passignano Outstanding restaurant in a 12th-century wine cellar inside Passignano monastery. Extraordinary setting and food. Book ahead.
DAY 5
LUCCA AND VOLTERRA
MORNING
LUCCA, THE MOST PERFECT WALLED MEDIEVAL CITY IN ITALY
Lucca is one of the great hidden gems of Tuscany. While Florence and Siena attract millions, Lucca receives far fewer visitors despite being arguably the most perfectly preserved medieval city in Italy. The 16th-century Renaissance walls, 4km in circumference, are so wide that a park runs along the top and locals cycle them every evening. The Duomo di San Martino contains the extraordinary Volto Santo, a wooden crucifix said to have been carved by Nicodemus who was present at the Crucifixion. Free to enter. Drive: 20 min walk around city
MIDDAY
LUCCA'S HIDDEN SQUARES AND ROMAN AMPHITHEATRE
The Piazza dell'Anfiteatro is one of the most extraordinary urban spaces in Italy, a perfect oval piazza built on the foundations of a Roman amphitheatre, with the oval shape still entirely preserved in the ring of medieval buildings. The Torre Guinigi has a garden of holm oak trees growing from its battlements at the top. The Basilica di San Frediano has an extraordinary 13th-century mosaic facade and a Romanesque interior almost always empty. Drive: 45 min drive to Volterra
AFTERNOON
VOLTERRA, THE ETRUSCAN CITY ON THE WINDSWEPT RIDGE
Volterra is one of the most extraordinary and overlooked cities in Tuscany. An ancient Etruscan city on a dramatic ridge 550 metres above the surrounding valleys, with views stretching 60km in every direction. The Museo Etrusco Guarnacci contains the finest collection of Etruscan funerary urns in the world, over 600 alabaster urns from the 4th to 1st century BC. The Roman theatre on the edge of the cliff is extraordinary and partially free to see from the public road.
💎 HIDDEN GEM
The alabaster workshops of Volterra have been producing carved alabaster objects since the Etruscan period. Several workshops still operate using traditional techniques and can be visited for free. The Cooperativa Artieri Alabastro on the Piazza dei Priori is the finest and offers free demonstrations of the ancient carving techniques.
🍽 WHERE TO EAT
Breakfast: Caffe di Simo, Lucca The most historic cafe in Lucca, where Puccini (who was born in Lucca) used to compose. Open since 1846. | Lunch: Ristorante Buca di Sant'Antonio, Lucca The finest traditional restaurant in Lucca. Tordelli lucchesi pasta, local rabbit and excellent Colline Lucchesi wine. | Dinner: Enoteca del Duca, Volterra Outstanding wine bar and restaurant in a medieval cellar. Local boar, truffle dishes and the finest local Vernaccia wine.
Where To Stay
Florence, Night 1 Hotel Lungarno, boutique hotel on the Arno in the Oltrarno. Approx 180 to 280 euros per night. Val d'Orcia, Night 2 Agriturismo near Pienza or Montalcino. Extraordinary farm stays from approx 120 to 200 euros. Chianti or Lucca, Nights 3 to 5 Rural agriturismo in the Chianti hills or Hotel Palazzo Alexander, Lucca. Approx 110 to 200 euros.
Top Tips
1. Book the Cappella Brancacci in Florence in advance online. Entry is timed and limited to 30 people.
2. Val d'Orcia sunrise requires leaving accommodation by 6am. The light lasts only 30 minutes.
3. The Abbazia di Sant'Antimo chants Gregorian at 7am, 12:45pm and 7pm. The 7pm service is most beautiful.
4. Siena Duomo floor is only fully uncovered in August and September. Check dates before visiting.
5. Book Trattoria Sostanza and Osteria Le Logge at least 2 weeks ahead. Both fill up extremely fast.
6. Tuscany restaurants close between lunch and dinner, typically 2:30 to 7pm. Plan accordingly.
Total Budget
110 to 180 euros/day