Tuscany Self-Drive

  • Tours & Multi-centres in Italy

Roll the windows down and breath in that fresh Tuscan air as you drive through the rolling countryside of olive groves, pines, cypresses and vineyards. With this self-drive itinerary and detailed driving routes, you’ll get to see the very best of Tuscany and the greatest thing is all the planning’s been done for you – so you can relax and enjoy the drive. It’s one of the finest wine producing regions in Italy and we’ve included a tour of the Brunello di Montalcino vineyard while you’re here - so you can taste for yourself. We’ve also organised lunch for you in Panzano – it’s the best place to try the famous Florentine steak. When you’re not dreaming of which tasty local snack to have next, you’ll be exploring Tuscany’s medieval towns and towering cities like Lucca, San Gimignano, Siena, Chianti and Florence to name a few.  

Tour highlights

  • Explore Tuscany at your own pace, visiting ancient towns and taking in the beautiful landscapes as you go
  • Wine tasting in Montalcino, the home of Brunello wine
  • Visit the villages of Lake Trasimeno
  • Take the Chiantigiana road, known as the wine road, that runs all the way from Siena to Florence
  • Lunch with a Solociccino menu at a renowned butchers in Panzano, with wine
  • See Florence, the Renaissance city, with its fine art and architecture
  • Receive detailed maps and suggested itineraries with the top places to visit

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Day 1: UK to Tuscany

When you arrive at Pisa Airport, collect your hire car and set off to your first stop…Lucca.

Day 2: Lucca and Pisa

Enter Lucca through the medieval city walls, designed by Leonardo Da Vinci - walk along the top to get your bearings and views across the terracotta roofs. We think the city’s best captured form above, so if you’re up for it, climb the 230 steps to the top of Torre Guinigi – panoramic views await. Looking down you’ll see the oval shaped Piazza dell’Anfiteatro, so pick the best cafe for a well-deserved cappuccino. Pisa’s next on the cards, with its famous leaning tower. Of course, you’ll have to get the obligatory photo where you're single headedly supporting it. But after, explore the old town, the cloistered gardens of Campositano or see the art at the Museo dell’Opera del Duomo. 

Meals included: Breakfast

Day 3: San Gimignano, Monteriggioni and Siena

Pack up your bags because today you’ll make your way to the Cortona area. On route make your first stop in San Gimignano – you’ll spot the fourteen tower houses rising above the skyline as you approach. Cobbled streets, ivy covered medieval buildings, fresco paintings inside the 12th century Duomo and little trattorias with chequered table cloths, all make up this beautiful hilltop town. Continue on the road to Monteriggioni, another medieval citadel – you’re bound to feel like you’ve stepped into a bygone time. From the Borgo Stomennano you’ll have the most amazing views across the Chianti vineyards. Siena’s architecture towers into the sky too. It's is an open-air museum with colourful streets, renaissance Palazzi and artistic treasures. Take a look inside the Duomo di Siena – it’s one of the finest cathedrals in Italy.

Meals included: Breakfast

Day 4: Montalcino, Pienza and Montepulciano

Take the old Cassia road through the vineyard strewn hills of the Val d’Orcia until you reach Montalcino. Here the mild winters and hot dry summers, make for ideal wine growing conditions – so today we’ve organised a wine tour, with a local producer, for you to taste the bold and fruity Brunello di Montaclino wine for yourself. Arrive in Pienza in time for an afternoon passeggiata around the Renaissance town, designed to perfection by Pope Pius II. The tiny town’s known for its pecorino cheese – so you’ll see bars offering cheese platters and wheels of it being sold in the deli’s. Montepulciano’s a little further on. Wander through the hilltop town, with its churches and crumbling Renaissance palaces that cluster around little piazzas, catching glimpses of the beautiful countryside in between.

Meals included: Breakfast

Day 5: Cortona and Lake Trasimeno Villages

Having stayed in the Cortona area for a few nights you’ll no doubt be itching to get out and explore the town on the hill. Art lovers should begin in the Museo Diocesano's, where there’s a small intimate collection, including works by Fra Angelico, Pietro Lorenzetti and Luca Signorelli. The Etruscan Academy Museum, with its extensive collection of Etruscan artefacts, is the place to go if you’d like to delve into the regions history. Otherwise, just enjoy a leisurely stroll soaking up the atmosphere. Lake Trasimeno’s on the border between Tuscany and Umbria – with enticing clear waters, it’s the perfect place for a swim. Spend the rest of the day hopping between the villages of Castiglione del Lago and Passignano and Arezzo on the lakes shores, visiting castles and Etruscan forts along the way.

Meals included: Breakfast

Day 6: Radda in Chianti, Panzano, Greve in Chianti and Impruneta

Making your way to your next night’s accommodation in Florence, take the Chiantigiana wine road. The scenic route connects all the main towns in Chianti and snakes its way through the hills, olive groves and vineyards. Stop off in Radda, the ancient capital of Chianti and historic wine town – give the Consorzio di Chianti Classico a try here. For lunch, we’ve booked you a table at a top butcher’s restaurant in Panzano – famous for being the best place for bistecca alla fiorentina (Florentine beefsteak). Later, in Greve wander through the long arcades of the ancient market town before making your last stop on the journey in Impruneta. Spot the terracotta pottery, made from local soil, as you wander through the town soaking up the lively local atmosphere - you might even catch a concert in the town square.

Meals included: Breakfast

Day 7: Florence and Fiesole

Florence, the cradle of the Renaissance – it’s a pretty nice place to spend part of your last full day. The city’s an art lovers dream. Walking through the centre you’ll stumble upon museums and churches – the Ufizzi Gallery with the world’s largest collection of Renaissance art and the Duomo, topped by Brunelleschi’s famous terracotta dome are a must while you’re here. You’ll have plenty of time for catch ups and cuppacino’s in pretty piazzas as you go. Later take a scenic drive up to Fiesole, the lesser known Etruscan stronghold where you’ll find yourself surrounded by cyprus trees and spectacular gardens, looking down to Florence and its beautiful sky line.

Meals included: Breakfast

Day 8: Tuscany to UK

Enjoy your final breakfast before heading to the Airport to return your hire car and fly home.

Meals included: Breakfast

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Your holiday includes

  • Car hire with unlimited mileage
  • 7 nights bed & breakfast in 4* country houses & hotels 
  • Wine tasting in Montalcino on day 4 
  • Lunch at a renowned butchers with a “Solociccino” menu: 4 kinds of veal, vegetables, dessert, wine and water
  • Detailed driving instructions, maps and suggested itineraries

Your holiday excludes:

  • Any extras, drinks and personal expenses
  • Entrance fees 
  • Parking costs (where applicable) 
  • Tourist tax 

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Please note that these hotels are subject to availability at the time of booking. If these are not available, they will be changed to hotels of a similar standard and location.

★★★★ Villa La Principessa, Lucca Area (2 nights)

★★★★ Borgo Il Melone, Cortona Area (3 nights)

★★★★ Villa Pitiana, Florence Area (2 nights)

Departure dates

  • Any day departure (subject to availability)

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This accommodation is not available to be booked online, please call our Reservations Team on 01483 791111 to book or for further information

Due to the constantly changing nature of the COVID-19 crisis, we may need to change or withdraw at short notice some advertised accommodation facilities and resort services to help keep everyone safe.

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