Arianna Occhipinti plucks a persimmon from a tree and passes it to me as we’re standing in the contrada of Santa Margherita, on the ancestral farmland that is now Chaza, her new hospitality project in southeastern Sicily. The sun is shining so bright that the fruit tastes like jam with a dash of Sicilian sunshine; sweet and sun-drunk, a moment that forced me to slow down. Later, by the pool at Casa Grande that looks over the entire span of Ragusa from a distance, the white stone of the Iblei mountains glowing in afternoon light, I open a bottle of her Grillo SM 2023 (grown on these very plots) and taste the same thing in the glass: minerality, warmth, and this specific place.
When I got wind that Arianna, who sparked the frappato grape’s renaissance, opened a hospitality project—and one in which I could lavishly overnight amidst her vines—I immediately booked a flight. Chaza (named after “la chaza,” the Sicilian word for piazza) is doing something more interesting than luring the cool kids: it aims to bring focus to Ragusa province, one of Sicily’s quietest corners. While much of the island battles overtourism, this southeastern stretch has remained overlooked.
“Chaza is an invitation to experience a different Sicily, far from stereotypes,” Arianna says. “A Sicily of earth, wind, seasons, and essential gestures. Here, time slows down, and the landscape is not a backdrop but a living presence.”
Book a flight to Catania (CTA), pick up your rental (Sixt is always a good idea), and plan for late spring through October when the countryside is at its most vibrant. From baroque towns to epic wineries and the best seafood eateries right by the sea, here’s everything to bookmark for Ragusa Province:
Chiaramonte Gulfi
Built from the white stone of the Iblei Mountains, Chaza sits in Contrada Santa Margherita, unfolding like a terrazza over Sicily’s most authentic self. “The architecture, inspired by tradition, blends harmoniously with the landscape, creating spaces that invite reflection and contemplation,” she says. “Every corner of Chaza is designed to offer a complete sensory experience, where the beauty of the territory is reflected in every element.” From her first hectare in Fossa di Lupo in 2004, Arianna has built a world rooted in respect; today her vines extend across ten contrade, with Santa Margherita being the latest. The Grillo SM vineyard spans across four plots: South Coast and North Coast yield salinity from chalk and fossils; Terrazza and Trefile bring flesh and acidity from stony clay-limestone.
There are two houses: Casa Grande, where I stayed, is a contemporary residence with a panoramic terrace and private pool. Casa di Pietra is more intimate, a restored stone house where original materials make every room atmospheric. The dispensa Occhipinti (estate products including pear jam, Tumminia wheat pasta, olive oil, wines, plus bottles from Arianna’s portfolio and from neighboring winemakers) arrives at your house. I preferred à la carte over the predetermined package; opening a bottle of mandarin juice or pulling a bottle off the wine shelf was never a bad idea. The Azienda Agricola Arianna Occhipinti online shop also means you can restock long after you’re gone. “Chaza is not just a place to stay, but a way of inhabiting the territory, of becoming part of it, even if only for a moment,” says Arianna.
There’s a notable contrada jeep tour to see how different soils produce distinct flavors, or the cooking class using ingredients from the vegetable garden. Winery visits let you taste her complete portfolio. For dining, Majore in the heart of the Iblei is a must. This family-run institution, established in 1896 and now in its fourth generation, has been perfecting the art of pork for over a century. The signature gelatina di maiale (pork jelly made with noble cuts set in clear aspic) is the dish everyone orders, though the risotto alla Majore, made with pork ragù and aged Ragusano cheese, and the stuffed pork rib run close seconds. Also worth visiting is Azienda Agricola Kalma, run by Waiata Kalma and Nikolas Resin, for their fresh, expressive wines.
Vittoria
A 30-minute drive south brings you to Frappato’s heartland, where Sicily’s only DOCG, Cerasuolo di Vittoria, named for its cherry-red color (“cerasa” in Sicilian), was born from the marriage of Frappato’s elegance and Nero d’Avola’s structure. “For me, Frappato is much more than a grape variety; it has been a traveling companion,” Arianna says. “I needed its elegance, its story to tell, its layered beauty, its oenological potential: Frappato took me by the hand and accompanied me as I built this path. At the same time, I believe it needed someone to harvest it with love and pride.”
It all started 22 years ago in Fossa di Lupo, where earth turns red in the evening and wind from the Iblei combs through the vines. That first hectare sits along the SP68, the oldest wine road ever recorded, connecting Gela to Kamarina three millennia ago. For generations, farmers walked it to bring wines to the coast. Her SP68 wine is named after this ancient road. From that single hectare, the estate has grown to 40 hectares across 10 contrade, including Bombolieri, where vines over two decades old stretch across limestone ridges (and why Il Frappato BB is so delicious), plus several hectares of ancient olive groves, Tumminia wheat, pear orchards, citrus, and vegetable gardens. It’s anything but just a winery.
The region's pioneering spirit lives at Azienda Agricola COS, founded in 1980 by Giambattista Cilia, Cirino Strano, and Arianna’s uncle, Giusto Occhipinti, where wines mature in terracotta amphorae rather than oak. After tasting my way through COS, I checked into Baglio Occhipinti, an eco-luxury retreat run by Arianna’s sister Fausta. I was handed freshly made almond milk at check-in instead of wine, which threw me off, but one sip explained everything—still the best almond milk I’ve ever tasted. It’s the kind of gesture that defines this place, serving what the land produces rather than what's expected. Book two nights for the Sicilian tiles, the pool shaded by fruit trees, and the restaurant that draws people from across Sicily. Breakfast is a regal event: freshly baked goods, local meats and cheeses, the most beautiful produce you’ve ever seen, and yes, a glass jar filled to the rim with the delicious almond milk.
For some of the best seafood in all of Sicily, head to reservation-only Ristorante Enogastronomico Sakalleo in Scoglitti, a fishing hamlet of Vittoria. This tiny 30-seat, no-menu spot serves fresh catch until you say basta. The vibrant French-Sicilian owner, Giada, is a highlight, making every trip feel like dining at a friend’s house.
Ragusa Ibla
A city with two souls: modern Ragusa Superiore above and baroque Ibla below. Rebuilt after the catastrophic 1693 earthquake, the most powerful in Italian history, the town produced Sicilian Baroque so magnificent that eight towns earned UNESCO status in 2002. At least 50 churches line the hillside. After gazing out at the panoramic views at Giardini Iblei, I deemed it one of the most breathtaking places I’ve ever visited. “Living in a baroque Sicilian town in 2025 is a gift in itself,” says Ciccio Sultano, the wildly talented chef behind two-Michelin-starred Duomo. “The time, the weather, the people allow for a quality of life that’s unmatched in cities like London and Milan.”
At Duomo, Sultano has spent years redrawing Sicily’s culinary cartography through what he calls “Cucina Educata,” or mindful cuisine. “It’s impossible to reduce everything to a single recipe; I’d rather talk about a food and wine cartography I’ve redrawn over the years, starting with the Sicilian Dominations, spanning 3,000 years of history,” he explains. “People and culture, that landed on the island at the center of the Mediterranean, not only plundered but also left behind flavours, ingredients, and techniques.” Dinner is full of edible theatrics. “Whoever sits at the table begins a journey through history and Sicily,” Sultano adds. Red prawn served three ways, pigeon with tonka bean, the greatest vegetable lasagna you’ve ever tasted; each dish is a lesson on Sicily.
Down the way, Gabriella Cicero, general manager of Ciccio Sultano Group, can often be found at I Banchi, where Sultano’s same philosophy can be enjoyed in a more casual setting. One taste of his arancino, and it’ll be hard to eat them anywhere else. “One of the dishes that captures the charm of these places is ricotta ravioli with festive meat sauce—handmade ravioli with ricotta from Masseria Ventosa, a filling that smells of the Hyblaean meadows, and the meat sauce that once graced family holidays,” says Cicero.
Beyond the restaurants, Cinabro Carrettieri is the only remaining workshop in Italy preserving the art of the carretto siciliano, those vibrantly painted Sicilian carts. Run by Damiano Rotella and Biagio Castilletti, the workshop caught Dolce & Gabbana’s attention; the duo hand-painted furniture for Domenico Dolce’s villa. It’s a living link to the patterns that have inspired the fashion house since its inception. In nearby Marina di Ragusa, Vossia il Mare pairs fish with thoughtful wines, Vota Vota offers refined food and wine, and Eretico is the wine bar you can't skip.
Stay at A.D. 1768, a boutique hotel whose origin story reads like fate. Owner Giusy Donato offered the same sum for an apartment in Milan and this crumbling palazzo; when Milan fell through, she poured everything into restoring the building. (The numbers 1768 have recurred throughout her life.) Walking through feels like stepping into someone’s art collectsion: paintings by Max Ferrigno, sculptures by Mariano Franzetti, and a room honoring her grandfather Don Nino, “[He was] the man I loved most and who inspired my way of life, even though he was just a farmer,” says Donato. The breakfast alone justifies the trip, a full-on, artsy sit-down affair with Donato’s homemade yogurt with Modica chocolate bits and candied mandarins that I’m still thinking about.
Modica
Modica is built down two valleys, with church domes rising from the descent. The town kept its medieval street plan after the 1693 rebuild, creating a vertical labyrinth where staircases become streets. It’s what captured the attention of Milanese architects Marco Giunta and Viviana Haddad all the way back in 2001. “It seemed like a city frozen in time; for us, it was love at first sight,” Giunta recalls. So they established Casa Talia, offering 12 suites arranged around a secret garden, and prompting slow living for all those who check in. My room opened onto a terrace with stairs leading to quiet coves. I spent an entire afternoon at the pool overlooking Modica, watching the town turn from gold to rose-pink at sunset while fig trees dropped fruit and church bells were the only way I kept track of the time. There’s a bar for guests, with a restaurant coming soon, and the most idyllic setting for breakfast one could imagine.
For dinner, Radici serves elevated Sicilian cuisine; Hemingway Bar handles the nightcap. And then there’s the chocolate, cold-processed below 40 degrees Celsius using a 16th-century Spanish technique, the only place preserving this ancient method. The sugar crystals never fully melt, creating a grainy texture and intense cocoa flavor that earned Europe's first PGI for chocolate in 2018. Antica Dolceria Bonajuto is the most famous shop, but Arianna and I swear by Sabadì. Bars studded with ginger, chili, and mandarin taste too good to be true (and you can also find them at Chaza in case you don’t make it to Modica).
Scicli
If you recognize Scicli’s honey-colored facades, you’ve probably seen Inspector Montalbano. Via Mormino Penna is one of Sicily’s most theatrical streetscapes, lined with facades adorned with apotropaic masks, grotesque faces meant to ward off evil. Cicero, originally from Scicli, suggests bookmarking the Church of San Bartolomeo’s Neapolitan nativity, or the curious Cristo con la gonnella. The Chiafura caves and San Matteo hill offer glimpses into Sicilian life, while Sampieri beach provides the perfect excuse to do nothing. Some of Arianna’s recommended eating stops are Prosit Sicilian Bistro, a favorite in town serving food that tells stories of family, and Mezzaparola or Carmelo down by the sea in Donnalucata. For local dishes, Cicero notes to keep an eye out for specialties like impanata di seppie e patate (cuttlefish and potato pie), impanata di lampuga (breaded dolphinfish), and cudduredde in musto (grape must dumplings).