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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.
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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.
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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.
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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.
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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.
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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.
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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.
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& 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.
