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.

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. Perched on the banks of the Arno River, this 16th Century estate is surrounded by 22 acres of lemon trees and olive groves, nestling between the rolling hills on the edge of Florence’s city limits.

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.

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. 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. Facing the perfect blue sea, between hills tipped with medieval forts, Il Pellicano rests on one of the most breathtaking seafront locations in Europe.

Wake 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. On today’s drive you will head towards the Tuscan hinterland, 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 for your next overnight stop, the fabulous Castello di Casole in Casole d’Elsa. This historic castle is set deep in the Tuscan countryside, having been converted into an exclusive boutique hotel – 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.

For 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 – as you follow the famous wine route Via Chiantigiana through the vineyards towards Florence. Your route will take you past two of the most beautiful medieval villages in Tuscany – Volterra and San Gimignano – perched high on the hilltops dominating the historic landscape. In the late afternoon, as you wind back through the Florentine hills into Florence, you will be heading for your final – and perhaps most elegant – destination, the exquisite Villa Cora. This aristocratic residence 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.

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 – and perhaps eat one more gelato.

Day 1Day 2Day 3Day 4Day 5
Tuscany & Porto Ercole - Day 1
Arrive in Florence and check in to Villa La Massa from 14:00, and spend an evening at leisure

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

Tuscany & Porto Ercole - Day 2
Your car will be delivered to the hotel after breakfast and we will do a short car and tour briefing before you start the first drive. This will take you south from Florence to the Montepulciano, from where the drive continues towards the coast. Arrive in Porto Ercole and check in to a hotel with the most astonishing sea view in the whole Tuscany – the luxurious Il Pellicano with an old authentic Tuscan charm.

Hotel: 5* Hotel Il Pellicano, Porto Ercole – 35 m² sea view double room
Driving time: 4 hours without stops

Tuscany & Porto Ercole - Day 3
After breakfast start your drive to Castello di Casole, one of the most beautiful hotels in the whole Tuscany. To get there you will drive a scenic route that also includes a stop in Bolgheri for lunch, where you will have the opportunity to stop at several local vineyards. Then the drive passes by Volterra, with some very enjoyable driving roads around it. Every time we go to Tuscany we fall in love even more with the roads, the scenery, and the people. Now it is your turn!

Overnight hotel: 5* Belmond Castello di Casole – 37 m² deluxe double room
Driving time: 3½ hours without stops

Tuscany & Porto Ercole - Day 4
For your final drive we have prepared a nice route through the Chianti regions of Tuscany. First stop is in San Gimignano, where we suggest you park the car and take a walk in this charming Tuscan town. From there the drive continues to Via Chiantigiana, the famous “Chianti route”, that takes you back to Florence through some picture perfect landscapes and towns. Spend your last evening at leisure exploring Florence city.

Hotel: 5* Villa Cora, Florence – 24 m² deluxe double room
Driving time: 4½ hours without stops

Tuscany & Porto Ercole - Day 5
Check out from Villa Cora is at 12:00, or if you wish you can extend your stay in Florence

Tour price calculator
Select the car you want to tour in and fill out the form to submit it to us to receive a bespoke tour quotation. We will check availability for the car and hotels on your requested dates, and reply to you by email or phone.

Included in tour price:
3 days car rental with insurance (680 km included)
4 nights accommodation for two, including breakfast
Programmed GPS with daily routes, roadbook & map
Personal meet + tour & car briefing with a member of our team
Full support by phone & email

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3 days / 680 km
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