Tuscany Self-Drive

  • Tours & Multi-centres in Italy

Road trip your way through the rolling Tuscan countryside, meandering the cultivated landscape, passing olive trees, pines, cypresses and vineyards of some of the finest wine producing grapes in the country. You’ll have the chance to sample some of the fruits, with a wine cellar tour and tasting of the world-famous Brunello di Montalcino. Explore some of Tuscany’s beautiful towns and cities such as Sienna and Florence home to magnificent examples of Renaissance art and architecture. Venture up to hill top towns like San Gimignano and medieval fortified villages like Cortona. Climb tall towers to catch birds-eye views of charming Tuscan towns and take in the hazed vistas across Tuscany.

2020 Departures on sale now!


Day 1: On arrival at Arrival at Pisa Airport make your way to the car hire desk to collect your car for the duration of the week. Set off from the airport in your hire car and head to your hotel in the Lucca area for your first nights stay.

Day 2: Wake up and enjoy a fresh and wholesome Breakfast at your hotel. Start your trip by exploring Lucca, the ancient fortified city set close to the Serchio river. Head for the sights, beginning at the Torre Guinigi to climb up the winding stairway to the top of the tower, you’ll be rewarded with incredible panoramic views over the city and the rolling Tuscan hills beyond. After, you’ll have earned a break, head for the oval shaped Piazza dell’Anfiteatro, surrounded by charming buildings and café terraces, the perfect spot for a cappuccino and watching the world go by. The heart of the city is pedestrianised, so take a stroll through the shaded arcades that run along each cobblestone street or wander along the tree lined city walls, designed by the one and only Leonardo Da Vinci, admiring the red roofed city as you go. Lucca, like many Tuscan towns, is dotted with ancient buildings and beautiful churches, we’d recommend visiting the basilica Chiesa di San Michele in Foro, with its intricate Romanesque façade. The building marks the point where the Roman Forum once was and is topped by a sculpture of Archangel Michael slaying the dragon. One you’ve taken in the sights continue on your Tuscan Journey to Pisa, the city known for its leaning tower. Of course, you’ll have to check out the world-famous landmark, but after, make your way into the old town where you’ll find the real local side to the city. It’s laden with architectural masterpieces such as the Duomo. Take some time out form sight seeing to enjoy the glorious Italian cuisine, choose from one of the local trattorias serving hearty Italian portions. Next, visit the cloistered gardens of Campositano or admire the intricate works of art at the Museo dell’Opera del Duomo or Palazzo Blu. Finally, make your way back to Lucca for your evening meal and a well-earned sleep!

Day 3: Pack up your bags and hit the road. Today, continue on your road trip to San Gimignano. The old town stands on the hilltop surrounded by 13th Century walls. As you approach, you’ll notice fourteen tower-houses rising above the town’s medieval buildings, that hark back to San Gimignano’s feudal past. The heart of the town is centred around the Piazza della Cisterna, where ivy covered medieval houses line the triangular piazza. Feel as though you’ve stepped into the past as you explore. Enter the 12th Century Duomo di San Gimignano to see the beautiful frescoes that adorn its walls. On route to your next stop, Sienna, visit the beautiful walled town of Monteriggioni. The walls form a perfect circular perimeter around the village and Medieval castle. Next to Sienna. Here too the architecture towers into the sky. This city is an open-air museum of renaissance Palazzi, artistic treasures and architectural masterpieces, where the colourful streets are dotted with artisanal boutiques, cafes, patisseries and restaurants. Home to one of the most striking cathedrals in central Italy, Duomo di Sinenna, its’s a strong contender as one of the finest Tuscan cities. The Gothic structure, built from the symbolic colours of Sienna in white and deep green almost black marble, is as stunning inside as it is out. Reaching the same height as the cathedral the Torre del Magna stands at 102m tall, symbolising the equal power between the church and the state. If you’re feeling energetic climb the narrow staircase to the top of the tower for spectacular views. Once you’ve taken in the sights head over to your new accommodation in the Cortona Area.

Day 4: Today your drive will take you on a journey through the cultivated landscape of vineyards and olive groves, rolling hills and towns of the Val d’Orcia. Make your first stop in Montalcino yet another enchanting fortified town. The town remains predominantly un changed since the 16th century with its ancient castle still standing pride of place. Montalcino has gained great wealth and fame for its bold and fruity Brunello wine over the years. According to wine critics it is some of the finest in Italy. Visit the wine cellars of a local producer, where you’ll have to opportunity to enjoy a glass of the fine Brunello. Continue on to Pienza, the perfect renaissance town, built by the ideas and visions of Pope Pious II. In the heart of the town is the central Piazza Pio II lined by the beautiful 16th century buildings including the popes summer residence Piccolomini Palace and the magnificent Cathedral, which was erected in the 15th Century and stood as a symbol of the Popes power. Not far from here, set on the hilltop, is the medieval village of Montepulciano. The Piazza Grande marks the heart of this charming village and remains the hub of village life to this day. Here stands the town hall, Palazzo Comunale, a castle like structure topped by a tall clock bell tower. After exploring this rural and romantic village return to your comfortable accommodation in the Cortona area.

Day 5: After staying in the Cortona area for the past few nights you’ll already have witnessed the stunning views from the walled hilltop town and be itching to get out and explore. Art lovers should begin in the Museo Diocesano's, home to a small and intimate collection, including works by Fra Angelico, Pietro Lorenzetti and Luca Signorelli. If its history you’re interested in the Etruscan Academy Museum is the place for you, with its extensive collection of Etruscan artefacts. Later make your way to the boarder between Tuscany and Umbria to the waters of lake Trasimeno. On the peninsula that juts out in to the lake lies the town of Castiglione del Lago. Etruscan temples once stood on these shores, which through history have been developed into equally significant structures. You’ll see the Corgna dynasty’s court palace, Palazzo della Corgna, which was built in the 16th Century to incorporate the original Baglioni Palace that dates back to 500. Today it houses a museum which celebrates the family’s history and is a hub for cultural events. Zig zag your way throught he cobbled streets to the far tip of the peninsula where you’ll find Rocca del Leone (the lion fortress) on the waterfront. The formidable fortress stands on the remains of an Etruscan site and was considered one of the most difficult to concur in Europe in the 16th century. Arch around the north of the lake to reach the historic fishing village of Passignano sul Trasimeno. It’s terracotta coloured architecture creates a vibrant contrast to the clear blue lake and lush green landscape behind. Wander through the cobbled streets and you’ll stumble upon the Rocca, yet another castle, but this one houses a boat museum. The final suggested stop for the day is Arezzo, which sits quietly in the Tuscan hills. The Piazza Grande was the towns market place in the middle ages, today it still acts as the hub of the town. Surrounded by beautiful buildings including a loggia designed by artist and architect Georgio Vassari. Stop in the square for a glass of local wine or take a look around some of the small antique shops. Finally, take a leisurely drive back to your accommodation in the Cortona area.

Day 6: Today we suggest you drive through the Chianti region over the awesome Chiantigiana road, stopping by Radda, the ancient capital of Chianti. Today the medieval town is most famous for its wine. Back on the Chiantigiana road drive on to Panzano with its towering Castle. The town is home to a renowned local butcher, where you can stop for lunch to enjoy the likes of bistecca alla fiorentina (Florentine beefsteak). Once your stomach is full get back to the road and meander your way to Greve to explore the ancient towns centre, its long arcades and ancient marketplace. Your last stop on the journey will be the charming Tuscan town of Impruneta. Spot the terracotta pottery, which is made from the local soil, as you wander through the town soaking up the lively local atmosphere. In the summer months you might even catch a concert in the town square. Make the last leg of your panoramic drive to the Florence area.

Day 7: On the final full day of your trip, spend the morning exploring the stunning city of Florence, also known as the cradle of the renaissance, home to so some of the finest examples of renaissance art and architecture in the world. Walk amongst it in the historical centre, starting with Piazza San Giovani taking a moment to admire the beautiful Italian Gothic façade of the City’s Duomo, topped by Brunelleschi’s famous terracotta dome. Using innovative design and techniques Brunelleschi’ had created the largest in the world. Seek out one on the many picturesque terraces lined by cafes, where you can enjoy a cappuccino, with a view. Next for the art. The Ufizzi Gallery holds one of the largest collections of renaissance art in the world. This may sound overwhelming, so why not choose a few rooms to explore. Spend a quiet moment admiring masterful works such as Botticelli’s ‘The Birth of Venus’ or  Michelangelo’s ‘Doni Tondo’. Once you’ve had a taste for what Florence has to offer take a scenic drive up to Fiesole. Set high above Florence this lesser known Etruscan stronghold was once a powerful rival to Florence. Wander through the walled town seeing stunning villas. Find yourself surrounded by cyprus trees and spectacular gardens, looking down to Florence and its beautiful sky line.

Day 8: Enjoy your final breakfast before heading to the Airport to retunr your hire car and fly home. 

What’s included

  • 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

Tour Excludes:

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

Your Hotels

Lucca Area - Villa La Principessa (2 nights)

Cortona Area - Borgo Il Melone (3 nights)

Florence Area - Villa Pitiana (2 nights)

Departure Dates

  • Any day departure (subject to availability)
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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