Our Tuscany & Porto Ercole luxury driving holiday is a magnificent journey of discovery through the famous wine regions and terroir of Tuscany. On your journey you will experience four of the finest hotels Italy has to offer, allowing you time to rest, indulge in the exclusive surroundings and absorb the true taste of Tuscany. Tuscany is world-famous for its elegant cypress-lined avenues, and roads winding through gentle green hills with lines of vineyards stretching to the horizon – an unforgettable driving experience you will enjoy throughout your journey. But Tuscany’s stunning coastline is also one of the most beautiful littorals in the Mediterranean.

On the day of your arrival in Florence you will check in to the first hotel of your trip, the stunning Villa La Massa, sister hotel of the famous Villa d’Este by Lake Como. The next morning after a sumptuous breakfast on the banks of the river, you will find your chosen supercar in front of the hotel ready for your first day’s driving. As you set off, your journey will take you deep into the Montepulciano region with its famous picture postcard vistas, following the wide sweeping country roads towards Porto Ercole, a charming seaside town on the Tuscan coast. The three other hotels you’ll be staying in on this Tuscan driving adventure – Il Pellicano in Porto Ercole, Belmond Castello di Casole in Casole d’Elsa, and Villa Cora in Florence – are exclusive hideaways situated in some of the best locations in the whole of Tuscany.

A true foodie or wine lover will appreciate the tasting experiences we’ve chosen for this adventure. Savour authentic Tuscan cuisine on our traditional lunch stops, explore tasting menus in Michelin starred restaurants in the evenings, and sample some of Tuscany’s best wine labels on our recommended winery visits during the day.

Our Tuscany & Porto Ercole supercar driving tour takes you on a wonderful adventure through elegant countryside that echoes with centuries of history and culture, combined with the luxury and indulgence of some of Europe’s most exclusive country retreats. Tuscany is one of the most perfect places in Europe for a road trip, with its rows of sun-drenched vines and honey-coloured fortified farmhouses, and behind the wheel of your supercar or classic car you will have the chance to enjoy the open roads and rediscover true driving pleasure, as you travel through this fabulous landscape.

Each stop on your itinerary is another opportunity to discover the charm of this world-famous region of Italy – be prepared to fall in love with a view, or a taste, or a feeling.

Day 1Day 2Day 3Day 4Day 5Extend your tour
Tuscany & Porto Ercole driving tour - Day 1Upon arrival in Florence you’ll transfer to the fabulous Villa La Massa and check in from 2 PM.

Perched on the banks of the Arno River, Villa La Massa is a 16th Century estate surrounded by 22 acres of lemon trees and olive groves, nestling among the rolling hills on the edge of Florence’s city limits. Walk in the grounds or stroll by the river, take a dip in the heated pool, or just enjoy a poolside drink overlooking the meandering Arno river, the hotel is a true oasis of calm on the edge of this bustling ancient city. Villa La Massa has a spa to die for, with separate rooms and chambers revealing hidden sunken baths, ice barrels, Turkish bath, sauna and full spa and treatment facilities. It’s the perfect place to revitalise and prepare yourself for the driving adventure of a lifetime. Of course, for those who would like to go exploring, Villa La Massa offer a shuttle service to the beautiful ancient center of Florence.

Once fully revitalised, you can begin to explore Villa La Massa’s extensive wine cellar. Enjoy an hour or two wandering around the authentic wine cellars, enjoy cheese and cold cuts with wine pairing, or simply browse the thousands of bottles in this mecca for any wine connoisseur. Villa La Massa’s beautiful vaulted restaurant Il Verrocchio has a stylish and intimate atmosphere with views out across the river to the famous Rufina hills beyond. Enjoy fresh local produce and imaginative cuisine in one of Florence’s finest restaurants.

Hotel: 5* Villa La Massa, Florence – 43 m² prestige double room

Tuscany & Porto Ercole driving tour - Day 2This morning your car will await you in front of the hotel following a sumptuous breakfast, and after a short personal tour briefing with our team you´ll be ready to begin your driving adventure. The first leg of your journey will take you south from Florence into the countryside to Montepulciano, where you’ll stop for lunch in a charming restaurant surrounded by ancient Florentine monuments. You’ll tour along elegant avenues flanked by cypress trees, through the fabulous Val d’Orcia region – now a UNESCO World Heritage site – with its world-famous honey coloured fields and rolling hills, towards your final destination – Monte Argentario on the Tuscan coast.

Set within its own estate on a majestic hilltop is one of the jewels of the Tyrrhenian coastline – Il Pellicano – where you can enjoy a Michelin starred meal by lamplight, or take an elevator cut into the hill from the clifftop pool, down to a breathtaking private beach to watch the sunrise. Facing the perfect blue sea, between hills tipped with medieval forts, Il Pellicano perches above one of the most breathtaking seafront locations in Europe.

For your dinner you might want to consider treating yourself to the hotel´s Michelin starred Il Pellicano Restaurant. In this fine dining restaurant chef Sebastiano Lombardi serves up the best of Italian cuisine made with top quality organic ingredients. Enjoy a stylish gastronomic experience with an unbeatable view and unforgettable atmosphere.

Hotel: 5* Hotel Il Pellicano, Porto Ercole – 35 m² sea view double room
Driving time: 4 hours plus stops

Tuscany & Porto Ercole driving tour - Day 3Wake up to the view of a glistening sea and enjoy an irresistible breakfast on Il Pellicano’s elegant terrace overlooking the silvery blue waters of the Mediterranean.

Today’s drive takes you on a varied landscape, on coastal roads overlooking the calm waters, into the hinterland behind the coast, pausing at the fortified village of Bolgheri, where you can visit the world-famous vineyards and wineries, meet local producers, and sample delicious wines over a typical Tuscan lunch using fresh, locally sourced specialities. This afternoon you head deeper into the countryside on the twisting remote back roads and on to your next overnight stop, the fabulous Belmond Castello di Casole in Casole d’Elsa. This historic castle is set deep in the Tuscan countryside, and has been converted into an exclusive boutique hotel – now considered by many to be among the best in the world – with breathtaking views over the rolling hills and bucolic panoramas. Castello di Casole is the perfect place to immerse yourself in the true spirit of Tuscany.

Tonight you´ll be able to enjoy a magnificent dinner in the hotel´s Tosca restaurant under the leadership of Executive Chef Daniele Sera. The focus is pure Italy – homemade pasta, locally sourced meat, exceptional seafood, garden-fresh produce, and of course, endless fresh bread and estate-grown extra virgin olive oil.

Overnight hotel: 5* Belmond Castello di Casole – 37 m² deluxe double room
Driving time: 4 hours plus stops

Tuscany & Porto Ercole driving tour - Day 4For the last day of your Tuscan driving adventure you will travel through some of the most dreamy picture perfect landscapes – on thrilling driving roads perfect for your supercar – following the famous wine route Via Chiantigiana through the Chianti vineyards towards Florence. Your route can best be described as ‘everyone’s dream of Tuscany’, and will take you past two of the most beautiful medieval villages in the region, both perched high on hilltops dominating the historic landscape, and providing an unforgettable backdrop for your journey. You’ll be able to stop for wine tasting in one of the area’s most famous wineries, and sample a huge selection of exclusive labels and purchase the best local produce.

In the late afternoon, as you wind back through the Florentine hills towards the ancient city, you’ll be heading for your final – and perhaps most elegant – destination, the exquisite Villa Cora in Florence. Once a splendid aristocratic residence, Villa Cora is located inside a centuries-old park that overlooks the famous Boboli Gardens, a short walk from the Piazzale Michelangelo with its unrivalled views over Florence’s historic skyline.

For your final night in Florence we’ll be able to reserve a table for you in one of Florence´s most sought after restaurants, depending on your mood – from Michelin starred fine dining to unforgettable ‘eat like a local’ experiences, we can recommend the very best on offer in this ancient Renaissance city.

Hotel: 5* Villa Cora, Florence – 24 m² deluxe double room
Driving time: 4 hours plus stops

Tuscany & Porto Ercole driving tour - Day 5Check out from Villa Cora is at 12:00, or if you wish you can extend your stay in Florence
Tuscany & Porto Ercole driving tour - Day 5If you would like to extend your tour to include more than 3 days of driving in Tuscany please contact our team for more information


Tour price calculator
Select the car of your choice for the perfect Tuscany & Porto Ercole driving tour, and submit the brief form below to receive a bespoke tour quotation. We’ll check availability for the car and hotels for your requested dates, and reply to you by email or phone.

Included in the tour price – the price is for two people sharing:
3 days car rental with insurance (all 700 kms included for the tour)
4 nights accommodation for two in a shared room, including breakfast
Preprogrammed GPS with a route for each touring day, bespoke roadbook & map
Personal meet + tour & car briefing with a member of our team
Full tour support by phone / WhatsApp & email

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Duration:
5 days / 4 nights
Touring:
3 days / 700 km
Available:
April-October
Tour start:
Florence
Price from:
€5299