Tuscany & Umbria: Ravishing Hotel Discoveries in Italy


The trouble with Tuscany is that it’s so picturesque it can take hours to get anywhere. On my recent journey, I resolved not to stop the car again unless I saw a view significantly more inspiring than the one I’d just pulled over to photograph. And then, around the next bend, there it was. It didn’t matter that I’d been to the region multiple times before. The combination of vineyards, olive groves, lines of cypress trees, old stone farmhouses and ancient hill towns remained as intoxicating as when I first saw it decades ago.

My delight was enhanced by having been deprived of Italy for the better part of two years. I’d come to take my frequent visits almost for granted. Thankfully, on this trip, hotels, restaurants, shops and sites were generally open to visitors, and COVID-19 protocols proved minimally intrusive. Italy felt rather normal; and normal in Italy is very good indeed.

In spite of everything, hotel standards in Tuscany only continue to improve. Property after property impressed me with exceptional accommodations, high levels of service and myriad amenities and activities. Twenty years ago, I looked for charm more than luxury. Now the region can boast some of the world’s finest full-service resorts. Moreover, they did not seem understaffed, like many properties in the United States, and they haven’t experienced the same degree of price inflation.

Belmond Castello di Casole

Entrance to Belmond Castello di Casole, Casole d'Elsa
Entrance to Belmond Castello di Casole, Casole d'Elsa - Photo by Andrew Harper editor

We rented a car at the Florence airport and made an easy hourlong drive down into the Chianti Colli Senesi wine region. Opened in 2018, the 39-room Belmond Castello di Casole is set on a 4,200-acre estate, centered on a hilltop village and castle. The oldest construction on the hill, a stone watchtower, dates from the late 10th century, but archaeological discoveries indicate occupation since at least the Etruscan era, between the eighth and third centuries B.C. (Notable local finds are displayed in the archaeological museum in nearby Colle di Val d’Elsa). The main palace dates substantially from the 19th century, but it was at its most glamorous in the mid-20th, when owner Conte Edoardo Visconti di Modrone, brother of the famous film director, hosted star-studded parties there.

We pulled up to the sandy-hued structure, fronting a large and fragrant rose garden. As one valet took care of our car and luggage, another escorted us to the front desk, passing first through a flower-filled entry hall with an extravagant onyx floor. Flutes of sparkling wine in hand, we followed a staff member on a short tour of the property before heading up to the second floor of the castle.

At Castello di Casole, the staff passed up few opportunities to impress us with their thoughtful and anticipatory service.

There, our Executive Junior Suite had a strong sense of place, with original terra-cotta floors, tall beamed ceilings and a décor of carved wood and wrought iron. In the separate living room, we found a velvet sofa and armchair. A small walk-in closet off the large bedroom provided plenty of storage, but the best feature of our accommodations was the capacious white-marble bath, stocked with Acqua di Parma products. I also appreciated the suite’s contemporary touches, including USB charging ports above the nightstands, an outlet inside the room safe, window screens and effective air-conditioning. Wooden shutters and heavy drapes ensured that the bedroom remained dark until well after sunrise, and it was a pleasure to open them each morning to flood the room with light and fresh air. On one side, we overlooked the rose garden, and on another, we had more sweeping views of the valley below.

We started each day with breakfast in the broad courtyard beside its central fountain. A buffet was laid out, but a waiter served us from it. One morning, we took a short hike, passing the contemporary Oliveto Suites, which have terraces with splendid views, before heading into shady oak forest. There, we spotted numerous birds and even startled a deer. Later, we lunched on a covered terrace, surrounded by geraniums, sharing a prosciutto-and-burrata-topped pizza while taking in the panorama of unspoiled countryside.

Ristorante Tosca terrace, Belmond Castello di Casole, Casole d’Elsa - Photo by Andrew Harper editor
Rose garden, Belmond Castello di Casole - Photo by Andrew Harper editor
Infinity pool overlooking the town of Casole d'Elsa - Photo by Andrew Harper editor
Bedroom of our Executive Junior Suite - Photo by Andrew Harper editor
Bath of our Executive Junior Suite - Photo by Andrew Harper editor
Bar Visconti - Photo by Andrew Harper editor
Pizza with burrata, arugula and prosciutto - Photo by Andrew Harper editor
A pillow of zuppa Inglese topped with raspberries and alchermes liqueur gelée, Ristorante Tosca - Photo by Andrew Harper editor

We spent that afternoon beside the wide infinity pool, pausing from our novels to gaze at the nearby hill town of Casole d’Elsa. On another day, I took advantage of the spa, which occupies a former winery next to an old church. In the cellars, hallways lined with contemporary marble sculptures and ancient Etruscan pieces led to men’s and women’s lounges (currently available only by advance reservation for private use, as at most hotel spas in Tuscany). I had the hot and cold pools, steam room and relaxation room all to myself, both before and after my restorative Signature Essere Massage performed by a talented therapist.

We returned to the terrace each evening for sunset cocktails. A pianist who accompanied our aperitifs moved into the Ristorante Tosca at dinnertime, playing a mix of jazz standards and Italian classics. The starburst chandeliers and colorful glassware — nearby Colle di Val d'Elsa is known for its crystal — provided an eye-catching counterpoint to the space’s exposed stone walls. I relished the pici pasta (like thick hand-rolled spaghetti) with sweet Sienese garlic and savory tomato sauce and the suckling pig topped with crunchy crackling and accompanied by dollops of sauerkraut and carrot purée. A glass of the Castello di Casole’s own Super Tuscan paired well with both.

At checkout, we were presented with a bottle of the wine to take home. When I requested that the valet bring our car around, I learned that it was already at the entrance — the concierge knew approximately when we were departing and had arranged for our vehicle to be ready for us. Overall, the staff passed up few opportunities to impress us with their thoughtful and anticipatory service.

- Hotels at a Glance -

Belmond Castello di Casole    97Andrew Harper Bird


The warm and anticipatory service; the strong sense of place; the opulent bath in our roomy Junior Suite; the sensational views from the pool and dining terrace; the well-marked hiking trails.


Glasses and plates accumulated on a table outside our room and remained there for half a day.

Good to Know

Suites in the Limonaia building are adjacent to the castle, but contemporary Oliveto Suites are a five-minute walk downhill; the hotel is within an hour of Siena, Monteriggioni, Colle di Val d’Elsa, San Gimignano and Volterra.

Rates: Executive Junior Suite, $1,400; Grandiosa Suite, $1,900
Address: Località Querceto, Casole d’Elsa, Siena
Telephone: (39) 057-796-1501

View Belmond Castello di Casole Listing

Il Borro

Main infinity pool, Il Borro, San Giustino Valdarno
Main infinity pool, Il Borro, San Giustino Valdarno - Photo by Andrew Harper editor

Whereas the Castello di Casole is a palazzo with additional buildings, Il Borro, just northwest of Arezzo, is a larger village turned resort. In 1993, Ferruccio Ferragamo, a scion of the famous shoe and luxury goods empire, purchased the small hill town, as well as the adjacent palace (now a 10-bedroom villa) and 2,700 acres of land. He and his son set about refurbishing the property, transforming it into a 58-room resort, complete with a spa, organic kitchen garden, winery, stables and three-hole golf course. Given its owners, one might expect Il Borro to be fashion-forward, but its style is mostly quite traditional, in keeping with the historic nature of the buildings.

At check-in, we were upgraded from a Junior Suite to a Deluxe Suite in the 38-room medieval village. (Guests can also book villa-like farmhouses or accommodations in the 18-room Aie compound, which has its own pool, but the village is more convenient to the amenities of the resort.) We left our car in the parking lot by reception, and a driver took us past the complex containing the spa, main pool, bar and two restaurants, up to the village itself. In addition to lodgings, the village has its own smaller infinity pool, though because it was unstaffed during our stay, we didn’t linger there. It also contains shops selling high-quality local textiles, jewelry and shoes.

Il Borro's 10-bedroom villa - Francesca Pagliai
View of the resort from our Principessa Suite - Photo by Andrew Harper editor
Bedroom of our Principessa Suite - Photo by Andrew Harper editor
Bath of our Principessa Suite - Photo by Andrew Harper editor
Spa pool - Francesca Pagliai
Pasture outside the stables, Il Borro - Photo by Andrew Harper editor

Our second-floor suite was just off the village square. From our bedroom, we enjoyed fine views of the forested ravine below. Inside, the wood-floored suite had hand-smoothed plaster walls and a pleasing color scheme of neutrals and pastels. The bedroom featured a woodburning fireplace facing the comfortably firm bed. An entry hall contained an espresso machine, a bottle of complimentary Il Borro rosé and a couple of armchairs. It connected to the spacious bath, which had closets on either side of the tub. The shower stall in a separate room was large, but it drained rather slowly.

Bar tables along the pool had the best views and provided an agreeable place in which to read and indulge in a treat from Il Borro’s gelato truck.

We could have called for a car to bring us back down to the wine cellars, but it was an easy enough five-minute walk. The cellars combine an original section dating from 1800 with new tunnels dug out in 2004. A guide led a small group of us on a short tour, before inviting us to a tasting. I was quite taken with the 2013 Bolle di Borro sparkling wine as well as the 2015 Alessandro dal Borro, a full-bodied Syrah poured from a magnum. We sampled additional Borro wines with dinner in the nearby Tuscan Bistro. I’d intended the Polissena Sangiovese to pair with spelt casarecce (whole-grain pasta) and a ragu of beef and mushroom, but the dish arrived topped with shredded rabbit instead. Fortunately, the combination still worked well. And the Bordeaux-style Il Borro blend also proved a good match for grilled poussin with chopped spinach. (The hotel’s other dining option is the more formal Osteria del Borro, which has well-spaced tables surrounding a central fireplace.)

The bistro’s terrace overlooked one end of the main infinity pool, which itself faced a leafy ravine. Bar tables along the pool had the best views; the loungers unfortunately faced away from the water. Still, they provided an agreeable place to read and indulge in a treat from Il Borro’s gelato truck. Nearby was an airy fitness room connected to the spa. There, I had a “Candle Massage With Wine Therapy.” Employing melted shea butter, the treatment was both pleasant and hydrating. Alas, I wasn’t able to relax in the spa lounge either before or after my massage, as I was sent on my way without so much as a glass of water.

- Hotels at a Glance -

Il Borro    93Andrew Harper Bird


The feel of staying in a private hill town; the traditional décor; our well-laid-out suite; the excellent wines made on-site in impressive cellars; the numerous amenities and activities, including horseback riding; the two infinity pools.


Our shower’s slow drain; the poolside loungers were inconvenient to the pool itself, and service there could be slow; the lack of lounge access in the spa.

Good to Know

It’s a scenic drive of about an hour and 15 minutes to La Verna, the tranquil mountainside retreat of St. Francis of Assisi.

Rates: Junior Suite Medieval Village, $500; Prestige Suite Medieval Village, $640
Address: Località Borro 1, San Giustino Valdarno
Telephone: (39) 055-977-053

View Il Borro Listing

Castello di Reschio

Castello di Reschio, Lisciano Niccone, Italy
Castello di Reschio, Lisciano Niccone, Italy - Philip Vile

Despite a few minor problems, I regretted departing our little private village and wished we’d had time to explore more of the estate. Driving southeast, we passed by the ever-popular towns of Arezzo and Cortona, before serpentining down a mountainside into a valley filled with forests and tobacco fields. Abutting Tuscany on the Umbrian side of the border is the 3,700-acre estate of Castello di Reschio, arguably the most anticipated resort to open in Italy this year. Its Instagram account has more than a quarter-million followers, due in no small part to its social media-friendly Gatsby-esque décor. On the way to reception in the circular 10th-century castle, I remarked that the jewel box of a bar looked quite stylish. “Yes,” my escort replied, “you’ll find that many things here are quite stylish.” And so they were.

One morning, we walked around the estate with a biologist guide, Marco. He proved equally knowledgeable about plants and the agricultural history of the region.

Between the vaulted reception lounge and the bar was the Palm Court, a plant-filled conservatory that provided an ideal place in the evening to relax with a barrel-aged Negroni. Upstairs was the indoor-outdoor gourmet restaurant, with a terrace overlooking a lush valley. Many items on the tasting menu were superb, including the fresh tagliolini with eel and smoked butter and the rich shredded venison topped with creamy dollops of eggplant. However, I’m not sure a Michelin star is in the restaurant’s immediate future. Certain courses, such as the bland and slightly overcooked turbot, were unsuccessful; a couple near us had to request missing silverware; and I overheard a waiter tell diners, incorrectly, that there were no Umbrian wines on the by-the-glass list.

Dinner at the more casual Ristorante Alle Scuderie, across from the world-class stables and riding ring, was an unqualified success. I started with egg tagliolini bathed in a sort of smoked soubise (onion sauce) and dressed with crunchy hazelnuts and shredded black truffle, before moving on to exceptionally tender pork ribs with sweet barbecue sauce and housemade potato chips. We dined on the covered patio, while being entertained by a jazz combo, before decamping to the bar inside for nightcaps.

Although it’s possible to use Castello di Reschio as a base for sightseeing, making day trips to places like Assisi (38 miles) and Perugia (25 miles), we contented ourselves with the on-site amenities. One morning, we walked around the estate with a biologist guide, Marco. He proved equally knowledgeable about plants and the agricultural history of the region. For example, he pointed out a species of maple that farmers once grew in their vineyards, using its branches to train the vines. The walk also gave us the chance to see some of the old stone farmhouses around the property, transformed into luxurious villas. Later, we relaxed on cushioned loungers beside the extravagantly lovely pool, a dark mirror reflecting mature umbrella pines and ancient castle walls. A centuries-old watchtower by the pool now functions as a bar, serving coffees, cocktails and panini.

Swimming pool, Castello di Reschio - Photo by Andrew Harper editor
Palm Court, Castello di Reschio - Photo by Andrew Harper editor
Terrace at Ristorante Al Castello - Photo by Andrew Harper editor
Bedroom of our Castello Suite - Photo by Andrew Harper editor
Daybed in our Castello Suite - Photo by Andrew Harper editor
Salad with mixed greens, flowers and fresh herbs - Photo by Andrew Harper editor
Seabass carpaccio with zucchini, ice plant and sesame - Photo by Andrew Harper editor

We reserved a 45-minute slot of private time in the spa’s wet area, which contains a sauna, steam room and two refreshing “experience showers.” And although we didn’t take advantage of the single treatment room, with its stone walls, dual soaking tubs and woodburning fireplace, I couldn’t resist booking a Watsu session in the wondrously atmospheric “Roman bath.” A stone barrel vault rose above a large saltwater pool, surrounded by glimmering candles. My therapist led me into the water, attached floats to my ankles and proceeded to move me about, gently stretching my limbs and sometimes swirling me around. The meditative experience induced a deep sense of relaxation. When it was finished, I waded through a narrow tunnel into an extraordinary second section of the pool, set beneath a three-story stone tower. There, a button activated a giant rainfall showerhead.

Back in our Castello Suite, we enjoyed the same chic 1920s and ’30s-inspired décor as in the rest of the hotel, with green and gold velvets, brass and original oil paintings contrasting the old terra-cotta floors and wood-beamed ceilings. A white-marble wet bar was topped with a gleaming espresso and cappuccino maker, while items in the minibar were all complimentary, including a bottle of gin infused with botanicals harvested on the property, as well as mixers, salty snacks and a chocolate cake. Through a thick arch was a clawfoot tub, and just beyond it, the rest of the bath. A dual vanity of gray marble and brass faced the shower stall in a cleverly converted window niche. Antique portraits and wooden dress forms enhanced the vintage feel of the bedroom, as did a dressing table resembling a cabinet of curiosities. It was a sublime place to sleep. Unfortunately, the ground-floor suite was not perfect. Its large windows faced the courtyard, making it necessary to draw the sheer curtains in order to have even minimal privacy.

Small caveats aside, Castello di Reschio is a wonderful place at which to relax for two or three days, enjoying hikes, horseback rides, cooking classes and spa treatments. It has an aristocratic feel, fostered by its impeccably attired owner who routinely made the rounds. Our fellow guests also tended to be well dressed, even at breakfast. But the atmosphere felt convivial, not aloof or snooty.

- Hotels at a Glance -

Castello di Reschio    95Andrew Harper Bird


The glamorous 1920s and ’30s-inspired décor; the magnificent spa treatment room and Roman bath; the romantic drinking and dining venues; the formal but amiable service; the impressive views; the world-class stables and riding ring; the striking pool.


Our ground-floor Castello Suite’s lack of privacy (San Michele suites are smaller but have better views); its slightly inconvenient furniture arrangement; the minor service issues in the main restaurant.

Good to Know

The usual roster of on-site activities — hiking, biking, cooking workshops, wine tasting, truffle hunting — is available, in addition to beekeeping, fishing and tennis on well-kept AstroTurf courts; “obsessively filming and taking photographs” is discouraged.

Rates: Suite San Michele, $1,480; Grand Suite, $2,160
Address: Tabaccaia di Reschio, Lisciano Niccone
Telephone: (39) 075-844-362

View Castello di Reschio Listing

Castello di Velona

View from our Junior Suite patio, Castello di Velona, Castelnuovo dell’Abate
View from our Junior Suite patio, Castello di Velona, Castelnuovo dell’Abate - Photo by Andrew Harper editor

Winding our way back up the mountainside, we emerged high above the shore of Lake Trasimeno. After skirting its northern shore, we paused for a tour and delicious lunch at Avignonesi, one of Montepulciano’s top wineries. We continued past Pienza, famous for its Renaissance square, and entered the stupendously scenic Val d’Orcia. This is the home of one of Italy’s greatest reds, Brunello di Montalcino, and some of its finest resorts, including the Rosewood Castiglion del Bosco, Castello Banfi – Il Borgo and, most convenient to the town of Montalcino and dramatic Romanesque Abbey of Sant’Antimo, the Castello di Velona.

From our patio, a vast sweep of countryside extended for miles: an iconic Tuscan patchwork of fields dotted with villas and slashed by a gleaming river.

Although portions of this 45-room resort date back a millennium, it nevertheless feels quite contemporary, perhaps because the property spent centuries in ruins before extensive restorations began in the late 1990s. A cypress allée led up through steep olive groves and vineyards surrounding the castle. A valet met us at the entrance, and the helpful concierge ushered us to the main lounge, a glassed-over former courtyard furnished with leather armchairs and sofas, where we completed check-in.

I had reserved a UNESCO View Terrace Junior Suite on the preferred side of the castle, but the views in every direction were magnificent. (On the opposite side was a wide valley backed by Mount Amiata.) From our patio, a vast sweep of countryside extended for miles: an iconic Tuscan patchwork of fields dotted with villas and slashed by a gleaming river, all bracketed by two hill towns. We took care not to miss the sunset.

A glass door led into our visually striking Junior Suite, where a travertine floor set off black-framed furnishings with burgundy fabrics. An elaborate rocaille floor lamp illuminated the writing desk, while opposite was a comfortable black linen sofa. Closets flanked the entrance to the bath. Unfortunately, the large shower stall’s doors didn’t quite meet the floor, resulting in puddles. The deep travertine tub — almost a plunge pool — was set into the floor and had a special tap allowing us to fill it with thermal spring water.

Main swimming pool, Castello di Velona - Photo by Andrew Harper editor
Bar terrace, Castello di Velona - Photo by Andrew Harper editor
Thermal hot tub in the spa - Castello di Velona
Bedroom of our UNESCO View Terrace Junior Suite - Photo by Andrew Harper editor
Bath of our UNESCO View Terrace Junior Suite - Photo by Andrew Harper editor
Housemade pappardelle with ragu of game at Settimo Senso restaurant - Photo by Andrew Harper editor
Terrace of the UNESCO View Terrace Suite, Castello di Velona, Castelnuovo dell’Abate - Castello di Velona

Naturally warm thermal spring water also fills Castello di Velona’s dramatic bilevel swimming pool, which has a tunnel connecting it to a smaller indoor pool. The upper section of the outdoor pool affords vistas of the hills leading up to Mount Amiata, while a higher terrace offers yet more loungers overlooking both pool and mountain. Nearby, we discovered a surprisingly well-equipped covered outdoor fitness center. The spa below was being used mostly for treatments — I enjoyed a rejuvenating “Brunello Ritual” including a wine-based scrub followed by a massage — but in normal times, the cellar spa lounge, steam room and thermal hot tub would be appealing places in which to relax.

We dined one night at Il Brunello, Castello di Velona’s intimate gourmet restaurant, trying the five-course Menu Amiata, which focused on regional products. I loved the chef’s complex combinations of rich, earthy flavors and aromatic herbs. Trout with roe and fresh herbs, quail grilled over beechwood and pine, and wild boar with parsnip were all attention-grabbing and delicious. Only the one-note cappellacci pasta, sauced with unappealing “porcini water,” missed the mark.

At the more casual Settimo Senso restaurant, both my housemade pappardelle with a ragu of game and the moist and smoky ombrina (drum) fish, served tableside from skewers atop an ember-filled log, were thoroughly satisfying. The experience was marred only by occasional shouting from the kitchen. Breakfast on Settimo Senso’s terrace was my favorite meal, however. What a way to start the day: sipping thick double espressos and dining on farm-fresh eggs with grilled local tomatoes, watching the early morning sun turn the timeless Val d’Orcia to emerald and gold.

Getting into Italy requires a bit more paperwork than before, but the reward for persistence is a treasure trove of incomparable moments like these. I’ve already started planning a return trip.

- Hotels at a Glance -

Castello di Velona    94Andrew Harper Bird


The stupendous view from our patio (and the fine views in all other directions); the location convenient to numerous wineries and sights; the bilevel outdoor thermal pool with panoramic views; our bath’s huge tub with a thermal water tap; the mostly excellent gourmet restaurant; breakfasting while overlooking the Val d’Orcia.


At checkout, there was no offer to help with luggage or retrieve our vehicle from the parking lot; our view wasn’t easy to see from inside the room; the poor seal of the shower door.

Good to Know

The resort has a dine-around program with a half-board package at eight restaurants outside the property, including two with Michelin stars.

Rates: UNESCO View Terrace Junior Suite, $1,070; Suite With Panoramic Terrace and Private Thermal Pool, $2,890
Address: Strada Provinciale della Badia di Sant’Antimo, Castelnuovo dell’Abate
Telephone: (39) 057-783-9002

View Castello di Velona Listing

Read more about our editor’s trip to Tuscany and Umbria

By Andrew Harper Editor Andrew Harper editors travel the world anonymously to give you the unvarnished truth about luxury hotels. Hotels have no idea who the editors are, so they are treated exactly as you might be.

Keep Reading