Tuscany
3
Day Itinerary •
Italy
Tuscany is one of the most visited regions in the world and still one of the most extraordinary. The challenge is finding the real Tuscany beneath the tourist surface. The cypresses, hilltop villages, Renaissance art and extraordinary food are all real but they are best experienced away from the crowds that fill Florence and Siena's most famous streets. This 3-day route goes beyond the obvious. Florence's hidden courtyards and overlooked masterpieces that most visitors walk straight past. The extraordinary Val d'Orcia landscape at dawn before the tour buses arrive. Siena's forgotten contrade neighbourhoods and the hilltop towns of the Crete Senesi that look exactly like a Renaissance painting come to life.
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
Most visitors queue for the Uffizi and miss extraordinary art scattered throughout the city for free. The Cappella Brancacci in the Oltrarno neighbourhood contains Masaccio's frescoes that taught Michelangelo how to paint, visited by a fraction of the Uffizi's crowds. The Museo dell'Opera del Duomo contains the original Gates of Paradise by Ghiberti and Michelangelo's unfinished Pieta, with almost no queues. The Chiostro dello Scalzo has extraordinary Andrea del Sarto monochrome frescoes and is free. All three are within 30 minutes walk. Drive: 15 min walk to Oltrarno
MIDDAY
OLTRARNO, THE FLORENCE MOST VISITORS MISS
Cross the Ponte Vecchio and enter the Oltrarno, the neighbourhood on the south bank of the Arno where Florentines have lived for centuries. The Piazza Santo Spirito is the finest square in Florence for authentic local life, lined with artisan workshops and cafes visited almost entirely by locals. The Basilica di Santo Spirito has a remarkable Brunelleschi interior almost always empty. The Piazzale Michelangelo above provides the finest panoramic view of Florence. Drive: 15 min walk to San Miniato
AFTERNOON
SAN MINIATO AL MONTE AND THE HIDDEN FLORENCE
San Miniato al Monte is arguably the most beautiful Romanesque church in Tuscany, perched on a hilltop above the Piazzale Michelangelo with extraordinary views over Florence and the surrounding hills. Built in 1013 and almost entirely unknown to the day-trippers who photograph the city from below. The walk up through the rose garden is extraordinary. The Benedictine monks still chant Vespers at 5:30pm and the sound echoing in the medieval interior is unforgettable.
💎 HIDDEN GEM
The Corridoio Vasariano, the secret elevated corridor built by Cosimo I de Medici in 1565 to walk unseen from the Palazzo Vecchio to the Pitti Palace, runs above the Ponte Vecchio and through the city for nearly a kilometre. Currently undergoing restoration but portions are sometimes open. The corridor contains hundreds of self-portraits from the Uffizi collection.
🍽 WHERE TO EAT
Breakfast: Caffe Rivoire, Piazza della Signoria The most beautiful cafe terrace in Florence overlooking the Piazza della Signoria. Strong espresso and cornetti. | Lunch: Trattoria Sostanza, Florence The oldest trattoria in Florence, opened in 1869. The butter pasta and T-bone steak are legendary. Book well ahead. | Dinner: Buca Mario, Florence The oldest restaurant in Florence, founded in 1886. Traditional Florentine cuisine in a beautiful historic cellar.
DAY 2
VAL D'ORCIA
MORNING
MIDDAY
PIENZA, THE IDEAL RENAISSANCE CITY
Pienza is one of the finest small cities in Italy. Pope Pius II had his entire birthplace village rebuilt in 1459 as the first ideal Renaissance city, designed by Bernardo Rossellino to embody Humanist principles. The result is an extraordinary cathedral, episcopal palace and town hall arranged around a perfect trapezoidal piazza. The views from the city walls over the Val d'Orcia are extraordinary. Buy Pecorino di Pienza cheese directly from the producers in the main street. Drive: 20 min drive to Montalcino
AFTERNOON
MONTALCINO AND BAGNO VIGNONI
Montalcino is the home of Brunello di Montalcino, one of Italy's greatest wines. The 14th-century fortress at the summit has extraordinary views and still functions as a wine bar within its ancient walls. Then drive 15 minutes to Bagno Vignoni, one of the most extraordinary villages in Tuscany. The main square is not a square but a thermal pool, a great Renaissance bathing 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 is one of the most beautiful Romanesque abbeys in Italy, standing alone in a valley below Montalcino surrounded by olive groves and cypress trees. Gregorian chant is sung by the resident monks at 7am, 12:45pm and 7pm. Attend one of these services in the extraordinary 12th-century church for the most moving experience in Tuscany. Free.
🍽 WHERE TO EAT
Breakfast: Bar in San Quirico d'Orcia Stop for coffee in the village before driving the dawn landscape road. Leave by 6:30am for the finest light. | Lunch: Trattoria Latte di Luna, Pienza The most beloved restaurant in Pienza. Local pici pasta, lamb and the finest Pecorino in Tuscany. Book ahead. | Dinner: Osteria di Porta al Cassero, Montalcino Outstanding traditional Sienese cuisine. Local cinghiale ragu, pici and Brunello wine at honest prices.
DAY 3
SIENA AND CRETE SENESI
MORNING
SIENA BEYOND THE PIAZZA DEL CAMPO
Siena is extraordinary but most visitors see only the Piazza del Campo and the Duomo. The real Siena is its 17 contrade, the ancient medieval neighbourhoods that still function as rival city-states. Each contrada has its own church, museum, fountain and fierce identity. Walk the Terzo di San Martino, the Terzo di Citta and the Terzo di Camollia to find the neighbourhood museums, each containing extraordinary art and the Palio horse race silks that define Sienese identity. Most are free. Drive: 15 min walk to Duomo
MIDDAY
THE SIENA DUOMO AND THE LIBRERIA PICCOLOMINI
The Siena Duomo is one of the finest Gothic cathedrals in Italy. But the extraordinary secret is inside: the Libreria Piccolomini, a room commissioned by Cardinal Piccolomini in 1502 and painted entirely by Pinturicchio with 10 extraordinary frescoes of the life of Pope Pius II. Entry approx 8 euros and usually far less crowded than the main cathedral. The floor of the Duomo, only fully uncovered in August and September, contains the finest marble inlay work in the world. Drive: 30 min drive to Crete Senesi
AFTERNOON
CRETE SENESI AND SAN GALGANO
The Crete Senesi is the extraordinary lunar clay landscape south of Siena, bare rolling hills in grey and ochre with isolated farmhouses and cypress trees that look exactly like a background detail from a Duccio painting. 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, with a field of grass where the nave once was.
💎 HIDDEN GEM
The Palazzo Pubblico in the Piazza del Campo contains the Sala del Mappamondo, with Simone Martini's extraordinary Maesta fresco of 1315 and the famous Allegory of Good and Bad Government by Ambrogio Lorenzetti, the most important surviving example of secular medieval painting in Italy. Entry approx 9 euros and far less crowded than the Uffizi. ourhiddenearth.com
🍽 WHERE TO EAT
Breakfast: Caffe Fiorella, Siena The finest coffee in Siena, in a beautiful old bar near the Piazza del Campo. Local ricciarelli almond cookies. | Lunch: Osteria Le Logge, Siena The most celebrated traditional restaurant in Siena. Pici al ragu, ribollita and the finest Chianti Classico. Book ahead. | Dinner: Trattoria Papei, Siena Beloved neighbourhood trattoria near the Piazza del Campo. Extremely generous portions, honest prices and excellent local wine.
DAY 4
MORNING
MIDDAY
AFTERNOON
💎 HIDDEN GEM
🍽 WHERE TO EAT
DAY 5
MORNING
MIDDAY
AFTERNOON
💎 HIDDEN GEM
🍽 WHERE TO EAT
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. Outstanding farm stays from approx 120 to 200 euros per night. Budget Option Florence: Hotel Davanzati from approx 90 euros. Siena: Palazzo Ravizza from approx 110 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