Italy is a bottomless destination, everywhere you turn there is something beautiful. And unless you’re giving yourself an Instagram detox, you’ll particularly see Tuscany blowing up your social feeds right now.
But everyone’s looking for that part of Italy they haven’t seen yet.
We’ve sorted a Tuscan itinerary to inspire your next trip, with guaranteed highlights you didn’t know existed.
5 Tuscan must-dos off the beaten path:
1. Explore little-known towns like Arezzo
Like Milan, Arezzo is an industrial city that isn’t usually on the generic tourist route but it’s a hidden gem. The peach-hued town centre has a noteworthy medieval square and many beautiful churches still baring Renaissance oil paintings and stained-glass windows.
I found out about Arezzo as it is a dear friend’s hometown, she shares this trait with many famous historic artists such as Michelangelo. This is where the luxury label Prada and Miu Miu were born, people! The local advice is to dine at Ristorante Il Cantuccio, a cozy restaurant, serving native cuisine to, well, locals.
Think wild boar ragu, rabbit, truffle with fresh pasta and fried creamy porcini mushrooms. I fell in love with a hole-in-the-wall deli called Antica Bottega Toscana on the main drag Corso Italia. Don’t forget the Prada outlet just outside the city – one of the best stocked in the country.
Arezzo borders the region of Umbria, famous for its roasted pork porchetta. Look out for places serving freshly caught, slaughtered and roasted pig from the hillside. Divine.
2. Stay in an old Catholic Monastery
The nuns practicing their faith at Castel Monastero more than 900 years ago would not recognise it today. Nestled in a lush green valley in the Tuscan hills, the out-of-the-way and silent monastery housed the faithful connected to the nearby Berardenga Abbey from circa 1044.
Since then, noble families have carefully restored the Medieval castle shrouded by cypress trees and it is one of the most unique stays in Italy.
Come for dinner at Gordon Ramsay’s gourmet Contrada restaurant or stay in one of the 74 rooms and suites or the on-site country villa in the thriving Chianti vineyard. Every detail glows with Tuscan style. Terracotta potted colour peppers the sun-drenched piazza where you have your breakfast by an ancient well and the stone walls are the same that were standing nearly 10 centuries ago.
The renaissance-era charm spills into the rooms, decorated with old woods, and marble-like fireplaces to set the rustic yet elegant scene of an authentic Tuscan dwelling.
The Ancient hamlet spoils its guests with three pools cascading into one another and a wellness spa that has landed the resort its place as a member of The Leading Hotels of the World.
The Chianti region is a two-hour drive from Rome and Castel Monastero is a hop and skip from the popular town of Sienna.
3. Take a dip where Sophia Loren spent her summers
Many flock to Cinque Terre and Lake Como for that Insta-worthy beach holiday but the Tuscan coast boasts many just-as-turquoise spots.
Firstly, the one-hour ferry ride to Isola del Giglio (in the province of Grosseto) will fulfil your crystal-clear seaside dreams.
If you’d rather stay on the mainland, Hotel il Pellicano is an iconic option for a ‘spoil yourself’ accommodation choice. If you don’t want to stay, you can pop in for cliffside lunch overlooking the Tyrrhenian Sea at the hotel’s Pelligrill Tuscan Grill.
Actress Sophia Loren, Josh Hartnett and Queen Juliana of the Netherlands have been frequent visitors in its 50-year history. The famous yellow and white-striped towel deck and jetty make for the perfect swim.
4. Hit the spa.
The largest ESPA center in Italy can be found at a true 12th-century castle on 300-hectares of the private estate Castello del Nero.
Signature treatments use homemade extra virgin olive oil from the on-site groves but if you’re after something on the cheaper side, pay €35 for the spa’s famous heat experience.
The five-step program starts with a gentle sauna, before properly sweating it out in a Turkish Bath (caldarium), followed by an ice scrub, infrared shower and a dip in the vitality pool (with five different pressure stations!)
The grounds at Castello del Nero boast some of the finest landscaping in Europe, so exploring the property and gobbling down as much prosciutto as you can at “La Taverna /by the pool” Tuscan Restaurant is also a must on this stop.
5. Hot air balloon excursion
Road tripping the Tuscan hills is the best way to get around the region but floating over the countryside is the supreme way to take in the view.
With villages perched on hillsides, landscape molded with olive trees, farm crops and Florence in the distance, most local hot air ballooning companies guarantee very happy customers.
Just make sure you wait for a clear day. Most tour companies in Florence can organise day trips over San Gimignano and Sienna but our pick would be seeing the Chianti countryside.
Balloon in Tuscany is a five-minute drive from Castello del Niro and the hotel can organise transfers and experiences.
6. Find a sunflower field
From June to August sunflowers are in full bloom. You’ll easily spot the bright fields while driving around Chianti, the trick is to pull over safely without causing traffic chaos. My favourite crop was located about 15-minutes drive out of Sienna on the Strada Provinciale 73 bis towards Sovicille.
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