Tuscan Delights

This tour is for those wanting to experience the scenic heart of Italy and it’s gastronomic delights in luxurious style. The route will take you to classic Tuscan towns, lesser known hillside villages, architectural wonders, and out of the way local wineries and restaurants, all while motoring through the remarkable rolling Tuscan countryside on the region’s best roads. Your evenings will be spent in some of Tuscany’s finest hotels, including unique former hamlets (‘borgos’) that have been painstakingly restored and converted to first class, 5-star residences. 

The itinerary

  • Day Day 1: Florence

    Accommodation: 5 Star Helvetia & Bristol Hotel, Florence

    Arriving at the Helvitia Hotel in the centre of Florence’s cultural centre, you’re but a short stroll from the many rich cultural highlights this city is so famous for. The Cathedral of Santa Maria del Fiore (Duomo), Ponte Vecchio, the Uffizi Gallery, Palazzo Vecchio, the Basilica of San Miniato al Monte, and of course, Michelangelo’s statue of David.

    The obvious cultural and architectural attractions aside, Florence is also known as a food lovers paradise. Besides the 6 Michelin starred restaurants, famed traditional local cuisine including bistecca alla fiorentina, lampredotto, papardelle al cinghiale and the region’s special brand of Gelato are served in the countless rustic, family run restaurants that line the medieval streets and alleyways.

  • Day Day 2: Florence to San Felice, via Siena

    Accommodation: 5 Star Borgo San Felice, San Felice

    In the morning, one of our team will have your car ready at the hotel, and after a brief hand-over, you’ll head out of Florence and soon find yourself on the ‘Via Chiantigiana’. Winding its way through the Chianti region, this stretch of road is known around the world for its wine and landscapes. The road passes through charming villages, vineyards, olive groves, and castles, while offering stunning views of the Tuscan countryside.

    The first break on route is Greve in Chianti, where you’ll visit the unusual triangular-shaped main square and can also tour the famed wine museum. Continuing with a short, leisurely drive through the undulating countryside, the tour breaks in Panzano, a rustic town known for its dominating medieval fortress and church, and also where we recommend lunching on the fine native Tuscan cuisine at our favourite local restaurant.

    Later in the afternoon you’ll arrive in Castellina, a beautifully fortified town with the impressive tunnel-like Via delle Volte running alongside the main street. For those with a historical bend, you can also visit the town’s renowned archaeological museum. A short drive from Castellina is one of the area’s most awarded wineries where you’ll enjoy a well-earned break over a tasting on the terrace with its panoramic views across the rolling Tuscan countryside.

    The star of the day 1 is the small city of Siena with its UNESCO listed historic centre perfectly preserving the charm and character of the Middle Ages. Alongside the grand Piazza del Campo and Palazzo Publicco is the stunning Siena Cathedral (Duomo di Siena), a masterpiece of Gothic and Romanesque art, housing priceless works by Donatello, Michelangelo, and Bernini. If you’re feeling energetic you can also climb the Torre del Mangia, a 102-meter-high tower that offers panoramic views of the city and the surrounding countryside.

    The final drive of the day winds its way through local hamlets and a handful of local castle estates that often have their own vineyards and wineries. You can drop into any of these that grab your interest, although we’ll also suggest one or two of our favourites for those that prefer a recommendation.

    Your base for the next two nights is the wonderful Borgo San Felice. This luxuriously converted hamlet, immersed in vineyards, cypress and olive groves, has its own in-house vintages and Michelin starred restaurant on-site.

  • Day Day 3: San Felice to San Felice, via Val d'Orcia

    Accommodation: 5 Star Borgo San Felice, San Felice

    Today’s route will guide you through some of Tuscany’s most beautiful landscapes, including the UNESCO listed Val d’Orcia.

    Our first break will be the town of Montalcino, renowned for its medieval passageways and locally produced wines; Rosso and Brunello di Montalcino. From here you’ll motor south to the heart of Val d’Orcia and the classic Tuscan countryside of rolling hills, sunflower fields, vineyards, and cypress-lined roads. This is the Tuscany of postcard images known the world over.
    After a couple of short detours to some of the more iconic regional views, you’ll break for lunch in the hillside town of Pienza, a renaissance settlement built to embody the Humanist vision of the ‘ideal city’. The town’s architecture seamlessly blends into the landscape, and along with the charming alleyways and small piazzas, the views over the Orcia Valley are second to none.

    Leaving Pienza, we’ll guide you to another spectacular viewing point before a short drive through the rolling hills to the walled hillside town of Montepulciano. The town’s terraces require a bit of uphill walking, but the views and delightful café lined main street and alleyways make it well worthwhile.

    We break-up the relaxing drive back to the Borgo San Felice with one last stop for you to put your feet up and take in the rolling countryside while basking in the afternoon sun. You can also take this chance to pick up some local delicacies to take back to the hotel with you.

  • Day Day 4: San Felice to Pignano

    Accommodation: 5 Star Borgo Pignano, Pignano

    Farewelling Borgo San Felice, today’s tour starts with a drive through some Chianti backcountry. For those with an eye for local ceramics, or if you just feel like a mid-morning coffee while taking an easy stroll through a sleepy Tuscan village, you can choose to pull over in Gaiole.

    From Gaiole, a gently winding drive will see you arrive nearby Radda, a picturesque town with a history of human settlement dating back to 2000 BC. Within its stone walls you can admire the Palazzo del Podestà and the Church of San Niccolò before making your way cross country along a local, driver-oriented back road to one of the jewels of Tuscany, San Gimignano.

    San Gimignano, a stand-alone UNESCO listed world heritage site, is one of the many notable medieval hillside towns of Tuscany however, what makes it unique is the number of skyscraping towers that mark its skyline. These structures were built around 700 years ago with as many as 70 soaring over the city at one time. These days there are only 10 or so left standing, but they still make a huge impression. Towers aside, the town has a Duomo with a stunning fresco lined interior, historic piazzas and alleys to explore, and the foodies can enjoy a plethora of options for lunch. “Dessert” today will be on the terrace of a nearby winery overlooking the endless hills surrounding San Gimignano.

    A further half hour drive through the Tuscan hills is the ancient town of Volterra, with structures still standing from the Etruscan period (5th and 6th century BC), as well as more prominent Roman era remnants such as the ancient spa and theatre ruins in the town centre. The historic main street of the town is home to handicraft vendors and shops selling the town’s modern claim to fame, hand-made alabaster carvings.

    Following a short, leisurely drive from Volterra, you’ll arrive at the magnificent Borgo Pignano, with it’s beautifully restored interiors, stone carved outdoor pool with distant Tuscan views, and their signature Green Michelin Starred restaurant.

  • Day Day 5: Pignano to Pignano, via San Galgano

    Accommodation: 5 Star Borgo Pignano, Pignano

    Today’s tour starts with a coffee break in one of the small cafés in the authentic hillside town of Radicondoli. The views here are typical Tuscan, albeit with the occasional accompanying geothermal smoke rising out of the ground in the distance.

    After passing through the town of Montieri, take a break to wander the unique, roofless remains of the Gothic Abbey of San Galgano, before lunching in one of our team’s favourite Tuscan restaurants nearby.

    Following a leisurely lunch, the drive turns north and on to the cascades and crystal blue rock pools outside Colle di Val d’Elsa, before entering the walled town itself. Besides its fortress, unique viewing points and impressive Old Town, Colle is known for its crystal glass, with the town accounting for over 90% of Italy’s production.

    Leaving Colle, you can look forward to a final, relaxing winery stop where you can sip on a wine or aperitivo while gazing out across the vineyards and countryside, knowing the Borgo Pignano is literally just around the corner.

  • Day Day 6: Pignano to Florence, via Pisa

    Accommodation: 5 Star Helvetia & Bristol Hotel, Florence

    Our final day touring begins with some fine backroads; both the scenery and the road itself are first class. Coffee in the morning will be taken in one of the quieter, less touristed towns along our route in a café very much favoured by the locals.

    Motoring west, the route will make its way to the famed Tuscan coast and the port city of Livorno. Lunch alongside the canals surrounding the 16th Century Fortezza Nuova and if you’re feeling energetic, take a walk to the seaside and the city’s other famous fort landmark, the 800-year-old Fortezza Vechhia.

    After lunch we visit one of Italy’s most famous landmarks, the Leaning Tower of Pisa. The famous, dubiously built structure located in the impressive Piazza dei Miracoli, is actually the freestanding bell tower of the neighbouring Pisa Cathedral and it’s Baptistry, which themselves are actually very much worth a stopover on their own.

    Making your way back towards Firenze, you’ll make one final stop in a historic hillside village before the final stretch to the Helvetia & Bristol Hotel. The remainder of your evening and tomorrow are yours to continue to explore the many Florentine attractions on your doorstep.

  • Day Day 7: Florence

    Enjoy a morning in the world class spa of the Helvetia & Bristol or check-out and further wander the galleries, cafes and Renaissance streets of this elegant city. 

  • & more

    If you’d like to extend or customise any part of the above tour, please let us know and we’ll tailor this itinerary to suit you.


This tour is a true indulgence for the senses, including your time spent behind the wheel. The tour features iconic Tuscan roads, such as the Via Chiantigiana, but also a series of hand-picked driver-focussed, secondary roads where the sinewy tarmac is so often complemented by jaw-dropping Tuscan panoramas.

The convertible version of the Vantage sports the same twin turbo V8 under it's sculpted bonnet, combined with cutting edge dynamics making it a complete open-air supercar.

Aston Martin V8 Vantage Convertible

Audi's first supercar, the R8 encompasses all the marque has learned via it's successful racing program, culminating in the superb, naturally aspirated V10. Inside, the R8 has the best interior in the business.

Audi R8 V10

A typically special Audi interior filled with the aural delight of that raucous twin turbo V8, the RS6 estate is our choice as the perfect touring all rounder.

Audi RS6

The ultimate in luxury British convertible touring, the Bentley Continental GTC pampers it occupants while still providing an extremely capable sports driving experience when called on.

Bentley Continental GTC

The understated coupe body of the most compact of the M cars conceals 335 horsepower, making it the perfect choice for tackling the flowing forest roads and passes of the Alps.


A technological tour de force that maintains the impeccable tactility expected of a Ferrari. The 296 GTB is a truly sensory experience; blistering acceleration, sublime mid-engined handling, and an addictive aural scream.

Ferrari 296 GTB

The most powerful Ferrari convertible ever produced has an epic 800 horsepower of naturally aspirated V12 at it's heart. Even for a V12 Ferrari, this striking machine is outrageously fast.

Ferrari 812 GTS

The most powerful normally aspirated Ferrari road car ever produced has an epic 800 horsepower V12 at it's heart. Even for a Ferrari, this striking machine is outrageously quick.

Ferrari 812 Superfast

The F8 Tributo is Ferrari's ultimate expression of usable supercar performance. The F8 is quite likely the most intoxicating way to cruise both The Alps & autobahns.

Ferrari F8 Tributo

The F8 Spider is Ferrari's ultimate expression of usable open-top supercar performance. The F8 is quite likely the most intoxicating way to cruise both The Alps & autobahns.

Ferrari F8 Spider

The potent twin turbo v8, the retractable hard top and sublime neutral handling of the Portofino make it one of the great touring supercars.

Ferrari Portofino

The Roma is considered by many to be the best looking Ferrari available today. It's 2+2 fastback layout, luxurious interior, precise balance and the performance of the twin turbo V8 make it an unrivalled choice as an alpine touring car.

Ferrari Roma

If Lamborghini has a 'user-friendly' car, the charismatic Huracan Evo is it. With it's high revving V10, the all-wheel-drive successor to the Gallardo is a manageable, yet thrilling supercar.

Lamborghini Huracán Evo

The Huracan Evo Spyder has all the performance and charisma of the fixed-roof Huracan but with the notable advantage of absorbing its occupants in the open-air acoustics of that howling V10.   

Lamborghini Huracán Evo Spyder

The pinnacle of the Aventador range, the Aventador SVJ is the ultimate Lamborghini experience in every way; open air motoring immersed in the thunder of a 6.5 litre, mid-engined V12.

Lamborghini Aventador SVJ Roadster

The pinnacle of Lamborghini's range, the Aventador 'hypercar' is an extreme experience in every way; fighter jet lines, a thundering mid-engined V12, all wheel drive, and that undeniable Italian charisma.

Lamborghini Aventador S

Stronger, lighter and faster than it's predecessor, the 720S is McLaren's most advanced iteration of an F1 derived supercar.

McLaren 720S Spider

The convertible version of Mercedes ultimate 2-seater compliments its enigmatic shape with the finest of AMG’s power units wedged under its shapely hood.


Arguably the most dramatic of all German sports coupes, this charismatic 2-seater compliments its enigmatic shape with the finest of AMG’s power units wedged under its shapely hood.


The current iteration of this most iconic of sports cars will captivate you with its ability to effortlessly consume autobahn miles and then precisely scythe its way across twisting mountain passes.

Porsche 911 Carrera Coupe

For those who prefer to immerse their senses in the crisp, fresh alpine air, the 911 cabriolet provides a unique open-top touring experience.

Porsche 911 Carrera Cabriolet

The GTS is the next step up the 911 performance ladder. The same classic shape and engineering of the 911 S but with a bit more of everything.

Porsche 911 GTS

The closest Porsche get to a race car that can be driven on the road. The GT3 RS is Porsche's most focused, uncompromised version of the 911.

Porsche 911 GT3 RS

If you haven't driven the turbo, you haven't yet experienced what a 911 is capable of. Just take a glance at the specification figures. As impressive as the are, the figures still don't do justice to the tactile experience that is an unleashed 911 turbo.

Porsche 911 Turbo

The Turbo S is ultimate road focussed 911. The cabriolet version takes an unparalleled performance experience and adds the elements. This is simply one of the best ways to take on the great alpine passes of Europe.

Porsche 911 Turbo S Cabriolet

Porsche's take on the accessible roadster, the Boxster combines all the marque's engineering know-how into a practical, mid-engined sportscar that never fails to entertain..

Porsche Boxster (718)


Simply choose the car you’d like to drive on this tour, fill out the short enquiry form with your details, preferred dates and any questions you might have and we’ll come back to you within 48 hours.

Prefer to talk to someone about your options?
Get in touch

The Tuscany Tour

7 Days/6 Nights.
The Car
Price / Couple
  • Aston Martin V8 Vantage Convertible
  • Audi R8 V10
  • Audi RS6
  • Bentley Continental GTC
  • BMW M2
  • Ferrari 296 GTB
  • Ferrari 812 GTS
  • Ferrari 812 Superfast
  • Ferrari F8 Tributo
  • Ferrari F8 Spider
  • Ferrari Portofino
  • Ferrari Roma
  • Lamborghini Huracán Evo
  • Lamborghini Huracán Evo Spyder
  • Lamborghini Aventador SVJ Roadster
  • Lamborghini Aventador S
  • McLaren 720S Spider
  • Mercedes AMG GT C
  • Mercedes AMG GT S
  • Porsche 911 Carrera Coupe
  • Porsche 911 Carrera Cabriolet
  • Porsche 911 GTS
  • Porsche 911 GT3 RS
  • Porsche 911 Turbo
  • Porsche 911 Turbo S Cabriolet
  • Porsche 718 Boxster

The map

Start in Florence, the Renaissance and artistic capital of Italy. Tour the heart of Tuscany through wonderfully preserved medieval hillside villages, visually stunning landscapes and wonderfully scenic backroads. From the rolling green hills we turn towards the Mediterranean and Pisa, with it’s famed leaning tower, before the short drive back to Florence.

  • 105 kms / 65 mi
    Florence, Italy
  • 165 kms / 105 mi
    San Felice
  • 200 kms / 125 mi
    Val d'Orcia, Italy
  • 75 kms / 48 mi
    Pignano, Italy
  • 150 kms / 95 mi
    San Galgano
  • 120 km / 75 mi
    Livorno, Italy
  • Florence, Italy