From Rugged Hilltops to Coastal Oases, Here’s How to Explore Tuscany From Top to Tail

The dream of luxuriating under the Tuscan sun has endured for decades—from vineyard-lined hills to hilltop hamlets and rolling olive groves, Tuscany remains an icon of northern Italian charm. There is perhaps no better place to indulge in three of life's greatest pleasures: art, nature and of course, pasta.

While I'm well acquainted with the region's famous cities (Florence and Siena continue to surprise and delight each time I visit), I've never roamed the countryside that flanks them. Long immortalised in literature and film—most notably by Under the Tuscan Sun, starring Diane Lane, which sparked a wave of global interest—if you want Italy at its most authentic, with lashings of soul and extra helpings of food, then you will find it in droves in Tuscany.

Ahead, the best hotels to explore the region from top to bottom.

Hilltop luxury: Borgo Pignano, Volterra

The vibe

Boasting perhaps the most charming (and photographed) pool in the whole region, this biodynamic, country estate is jaw-droppingly exquisite. Perched above the ancient Etruscan town of Volterra, Borgo Pignano's preserved stone walls and 750 acres of biodynamic farmland—from olive groves to rolling vineyards—evoke the timeless charm of rural Tuscany.

What stands out immediately is the layout of the estate: an outdoor bar and seating area is perfectly positioned for knocking back Negronis, while you watch the tumbling plains shift from lush green to umber and ochre at sunset.

The service is impeccable—this is luxury at its most unfussy, with a generous helping of heart. The estate is overseen by Gigi, longtime Head of Guest Relations, who was born just over the hill. He's a true character, picking up guests in his caddy to tour them around the expansive grounds, where he will then invite them to feed the livestock and pluck ripe tomatoes straight from the vine.

The rooms

There are 14 rooms and suites in the main villa, as well as 10 authentically restored maisonettes and six private villas, including a farmhouse, which sleeps 20, and a former medieval priest's house, which houses two. The team takes bookings strategically to ensure that the estate never feels crowded, but if you're keen for more privacy, consider the private villas, which are nestled by the woods, vineyards, and lakes.

The interiors are unique to each room, and are a masterclass in olde worlde Tuscan design. I was so taken with the pale, duck-egg blue of my room that I had to ask for the exact paint shade (it's long out of production, sadly)—but the view of Volterra laid out in all its glory, from my perch in the tower, more than made up for it. All the rooms are expansive, and many come with original frescoes and four-poster beds.

Food and drink

Dining is split between two main restaurants, though you can have light bites poolside. Al Fresco offers relaxed fare, like wood-fired pizza and hearty pasta dishes, in the estate's garden, replete with a gelato truck, which dishes out free scoops all day long.

On the other end of the spectrum, their Michelin-starred Villa Pignano elevates traditional Tuscan staples. The views are breathtaking; guests can watch the sunset disappear between the hills as they feast on inventive dishes, conjured up by Chef Stefano Cavallini. Highlights include a deceptively simple fusilli pasta, cooked in fish stew extraction, and elevated through "onion air" and "seaweed bread crumble", as well as their highly decadent signature dish: papardella filled with a umami-rich rabbit ragu.

If you want something more laid back, book in for the bi-monthly barbecue that the staff puts on in the estate's vineyard—it's a great chance to connect with other guests in a relaxed setting, if that's your thing.

All produce hails from the estate—those tomatoes I sampled with Gigi? Very likely on my plate by nightfall. The team rear free range pigs, hens and bees, and cultivates overflowing herb and vegetable gardens. They also mill their own flour at their on-site bakery.

Industrious guests can blend their own organic lavender soaps and skincare tinctures, though if you're less creative, you can buy them and their excellent olive oil to take away.

Activities and Amenities

As for amenities, the infinity pool is a thing of beauty, carved directly into the hillside and complete with its own dedicated bar and staff. The spa is equally considered. Guests can book private slots in the spacious hammam to enjoy saunas, steam baths, and cold plunges, followed by locally harvested loose-leaf teas. Don't skip the treatments, too: my full-body massage was so good I drifted off.

There are a plethora of activities for the adventurous, ranging from apiary tours, forest bathing, horse riding, truffle hunting, and artisanal workshops—I personally went for the pasta making class with head chef Stefano Cavallini.

Borgo Pignano offers rooms from €350 per night based on two adults staying in the Villa, on a B&B basis. borgopignano.com

Costal calm: L'Andana Resort, Castiglione della Pescaia

The vibe

A couple of hours downstream, and you'll arrive in the seaside town of Castiglione della Pescaia in Maremma—one of southern Italy's most discreet coastlines. It's ancient fortress overlooks the pale twinkling shores of the Tyrrhenian sea, an expanse bordered by miles of sandy beaches and pine groves.

La Andana is the former hunting lodge of the last grand duke of Tuscany, Grand Duke Leopold II, and certainly the first impression of the estate—a half-mile driveway lined with cypress trees—is befitting of royalty.

The resort is sprawling and excellently turned out; the design marries Medici excess with French influences. But the layout is decidedly unfussy, and guests are allowed to roam as they please, ideally with a spritz in hand, or off into the countryside on one of their baby blue e-bikes.

The rooms

L'Andana has 50 rooms and suites in the main villa and farmhouse building. It also has a private villa, La Scuderia—the former stable of the Grand Duke's hunting reserve—which sleeps four, and has its own private pool.

Rooms are spacious, with ample space for clothing and absolutely gigantic bathrooms, finished with tubs and waterfall showers, big enough for two. The interiors here are elevated—it's not exactly the rustic Tuscan design that you may expect; instead, Ettore Mochetti, the chief editor of Architectural Digest Italy, designed the interiors, opting for more of an opulent feel.

Food and drink

The food at L'Andana was some of the best I had in the region. Don't skip out on La Villa, the more relaxed, all-day restaurant—sit outside on the veranda if you can; the light her, is jaw-dropping. Breakfast is excellent, but dinner—in that glimmering, pink-red light before sunset—is a must. Go for the taglioni with prawns, lemon and buratta. It's so good I had it three nights in a row.

If you're celebrating something special, ensure you book a table in advance at the resort's Michelin-starred fine dining restaurant, La Trattoria Enrico Bartolini, which fuses regional dishes with Mediterranean zest. While you can order à la carte, the tasting menu and accompanying wine pairing are beautifully crafted and worth the resulting heaviness.

There's also the option to order a picnic and dine amongst the vineyards—or if you fancy a trip to the nearby beach, staff can prepare a takeaway lunch. Wine and olive oil are produced on site—you can sample some of the former at the resort's Tenuta La Badiola Wine Shop, where you have a tour of the vineyard or partake in a tasting.

Activities and amenities

Ensure you pack a good book to read by the pool, which is nestled near a throng of shady pine trees. Inside, you'll find top-tier spa facilities, including a Turkish hamaam, and ESPA face and body treatments.

Feeling active? Begin your mornings with yoga or pilates underneath swaying pines, and then follow it with a few rounds of tennis, golf, or horseback riding. There's also biking, hiking, and Nordic walking trails through the sun-dappled hills, as well as cooking classes with the resort's chefs. Ensure you take the daily shuttle to the beaches of Castiglione della Pescaia, or if you fancy a city break, Maremma is just a stone's throw from the likes of Siena or Pitigliano.

L’Andana, Tuscany, offers double rooms from €440 per night based on two sharing, including breakfast. www.andana.it

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