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Holiday in Italy: Favorite Finds in Florence, Naples, Puglia and Rome

I've been traveling to Italy over the holidays with my family since I was a child, and while a visit during the winter season may mean no beach clubs or boating at the coastal beauties, or the odd raincloud hanging over the Duomo, I have always appreciated the relaxed warmth and authenticity that can be enjoyed there at that time of year. Below are some of my recommendations, including beloved spots and new discoveries, from our latest trip—which wandered down Italy's boot, beginning in Florence and ending in Rome, with stops in Orvieto, Naples and Puglia, along the way.


  • STAY: This year, we stayed at the Four Seasons, which is at least a fifteen-minute walk from central Florence and most popular attractions—but it wows with its palazzo location, beautiful gardens and pampering amenities. My favorite feature of the property is the beautiful frescoes that can be found throughout the lobby, especially in the chapel (the mansions the hotel occupies date back to the 15th and 16th centuries)—but the bespoke negroni menu in the Atrium bar and the pillowy beds are also highlights. (I also recommend drawing a bath in one of the clawfoot tubs and watching A Room with a View—and stash a few of the Angeli di Firenze hand soaps—from Officina Profumo-Farmaceutica di Santa Maria Novella—in your luggage to bring home.) The new hotels on my radar? The design-minded IL Tornabuoni, which opened in the fall of 2021 on Florence's primary luxury fashion street (just across from the Palazzo Strozzi), and Collegio alla Querce, an Auberge Resorts Collection property that will open later this year on the outskirts of the city, halfway to the Medici haunt of Fiesole.
  • EAT: If I could have only one meal in Florence (and only one meal left on this earth), it would be at Buca Lapi. This address is hardly a secret—it's alleged to be the oldest restaurant in Florence, dating back to 1880—and it's known to be a top spot for Bistecca alla Fiorentina, for both visitors and locals (and celebrities). The food is traditional and exceptional—and there are always daily specials worth making room for—but the real reason I continue coming back here is the chef and owner, Luciano Ghinassi, who has brought me to tears on more than one occasion with his one-of-a-kind hospitality. (Also, I love the vintage travel posters, postcards and doodles that plaster the cellar's ceilings.) The rigatoni at Trattoria 13 (Tredici) Gobbi, the pappardelle at Trattoria Sergio Gozzi and the bistecca (again) at Ristorante Buca Mario are the others I'd include if my last meal on earth permitted multiple courses. I did manage to squeeze in a visit to one new establishment—the latest opening from the brand behind Enoteca Pitti Gola e Cantina, another favorite spot on the other side of the Arno (directly facing the Pitti Palace). A more formal dinner in comparison to the Enoteca experience, Osteria dell'Enoteca presents a refreshing, contemporary take on Tuscan heritage—and (like at the original location) the wine selection is a standout (there's no list—instead, the sommelier will walk you through the offerings, literally).
  • DRINK: One of Florence's buzziest cocktail bars is Locale, which shook things up when it was named to the World's 50 Best Bars list in 2022 (and again this past year). In a city brimming with wine bars, Il Santino is intimate and lovely (it also has a sister restaurant next door). I did not make it to Gunè, but I hope to next time.
  • SHOP: The quality and authenticity of the San Lorenzo leather market has gone downhill in the last decade due to an influx of foreign vendors. Two family-owned boutiques with more unique Florentine designs are Pelletteria Artigiana Viviani and I'Mago (founded in 1965 and 1994, respectively); the Scuola del Cuoio, while touristy, is also a heritage establishment worth visiting. And for less expensive, typical gifts and souvenirs, the Mercato Nuovo (the smaller market, with the wild boar statue) is generally considered to be superior.
  • SEE/DO: The Palazzo Medici Ricciardi was an intriguing rediscovery, with its beautiful Cappella dei Magi (designed by Michelozzo and featuring frescoes by Benozzo Gozzoli) and Baroque Hall of Mirrors. The former seat of the Medici, today it is both a museum and the seat of the Metropolitan City of Florence. It also hosts rotating exhibitions, and the display of the Renaissance-style 20th-century paintings by Federigo Angeli was particularly interesting (the exhibition concluded in January). In the church of Santa Croce, Giotto's famous 14th-century frescoes decorating the Bardi Chapel are currently under restoration. Later this spring, the Fondazione Palazzo Strozzi will host a landmark exhibition of works by German artist Anselm Kiefer, "Fallen Angels" (on March 22 to July 21).


  • STAY: Orvieto is typically included as a day trip for an itinerary that is based anywhere between Florence and Rome. But a stylish new boutique hotel, Palazzo Petrvs, could change that. Located within a 15th-century mansion, the property contains nine rooms and suites and an inner courtyard with a restaurant and bar. As the name implies, a standout aesthetic element is local stone.
  • EAT/DRINK: Further afield in the Tuscany/Umbria region, Castello di Fighine is a cozy one-Michelin-starred restaurant from chefs Francesco Nunziata and Heinz Beck, housed in a medieval estate outside the town of San Casciano dei Bagni (the restaurant is temporarily closed and will reopen March 20). For a more rustic meal, also in San Casciano dei Bagni, Daniela is a beloved family favorite. This area of Italy is also a great place to try true farm-to-table cuisine—at one of the many family-run restaurants attached to agrotourism establishments.
  • SHOP: L'Orvietan is a historic boutique down the street from the Duomo sells local goods like olive-wood serving bowls and boards, linen towels, ceramics, olive oils and spreads—but it's also here that Orvieto's namesake herbal bitters tincture—dating back to 1603—is being revived for 21st-century ailments.
  • SHOP: One of Orvieto's true hidden gems, Orogami is an exquisite jewelry atelier run by husband-wife duo Massimo and Tiziana Aloisio and their daughter Angelica. Working primarily with gold, silver and gemstones, they design intricate, singular pieces that are inspired by time, the elements of nature and emotions like joy, hope and love.


  • STAY: The luxury hotel offerings in Naples are lacking—but a new opening on the horizon holds major promise: Rocco Forte just announced a new project in collaboration with fashion company Capri Group, Palazzo Sirignano, which is scheduled to open in 2027.
  • EAT: It's the million-dollar question: Who makes the best pizza in Naples? It may be one of life's great mysteries, but local consensus (if such a thing exists in Naples) left me with 50 Kalo, Ristorante Ciro and Antonio & Antonio as some of the top contenders. I will have to come back for 50 Kalo, but my personal favorite of the places I tried, which was also a local recommendation, was Concettina ai Tre Santi. The atmosphere was hip, there's a massive, fresh green salad on the menu that you can enjoy before the carbo-loading, and every table is christened with its own pot of basil for some DIY seasoning. For a break from pizza, La Scialuppa has wonderful fresh seafood and pastas.
  • DRINK: Caffè Gambrinus is the spot in Naples for a coffee. This historic café dates back to 1860 and is still popular with locals despite its fame. (And on the other side of the marina, I was told Chalet Ciro Gelato is the place to go for something sweet.)
  • SEE/DO: Naples does not get enough credit for its enormous artistic and architectural wealth. The National Archaeological Museum (Museo archeologico nazionale di Napoli) and the Sansevero Chapel Museum, with its lauded veiled Christ statue, are top sites. I was also impressed by the marble work and decorated arches of the church of Gesù Nuovo, and I hope to return to see the frescoes of the Giorgio Vasari Sacristy. Plus, says Indagare founder Melissa Biggs Bradley: "The Museo di Capodimonte is the largest museum in Italy and one of its least known. Built as a palace for Charles VII of Naples, it has more than 100 rooms containing an incredible collection, including Titians, Raphaels and many other Renaissance masterpieces, as well as period rooms and antiquities. It is an under-the-radar cultural powerhouse that cannot be missed."


  • STAY: Borgo Egnazia is a mini city of a resort, tucked away in a very quiet corner of Puglia, on the Adriatic Sea. Surrounded by fishing villages—but within an easy drive of towns like Alberobello, Monopoli, Ostuni and Bari—Borgo Egnazia has a main house with 63 rooms, from which radiate 28 pool villas and 93 borgos, one- and two-bedroom houses. Owner Aldo Melpignano, who is also an architect, designed his city from the ground up, with a blend of ancient-looking traditional structures and minimalist interiors that emphasize natural materials and the movement of light (from candles, glass lamps and the sunshine outside). There are three excellent restaurants—a fine-dining concept, a trattoria-style restaurant and a casual pizzeria—as well as a luxe spa and gym, a tempting boutique, tennis courts (and access to a nearby golf course), and, for the summer, a multitude of pools and terraces for lounging. The heart of the property is the central piazza, and over the holidays, the hotel hosts a magical Christmas market, with a truly lavish spread of olives (sourced on-property) and other typical snacks, as well as stands for wine, Pugliese artisans, performers and entertainments for children. It is one of the finest Christmas markets I've ever experienced—and it's another reason to come here in the off-season.
  • EAT: A favorite meal in Monopoli was Ristorante Lidobianco, where the squid ink risotto was perfectly portioned, the white wine was ice-cold and the views were bright blue.
  • SHOP: Ceramics shopping continued—with distinct Pugliese craftsmanship—at Artigianato Di Suma Maria (Suma Ceramiche) in Ostuni. In Locorotondo, N’Claud sells beautiful wool and silk shawls as well as clothing made from African fabrics.
  • SEE/DO: Memorable adventures are guaranteed with driver-guide Pino—who hosted Stanley Tucci when he filmed the Puglia episode of Searching for Italy—and history and wine specialist Mimmo, who leads a fascinating behind-the-scenes tour of the famous trulli houses. (Email info@indagare.com to learn more.)


  • STAY: We spent less than 24 hours in Rome—connecting to our flight home—which was nowhere near enough time to experience all that is new in the city, including the fantastic Six Senses, the brand’s first hotel in Italy, which opened last spring. Housed within a UNESCO-protected, 18th-century Baroque palazzo on the Piazza di San Marcello, just steps from the Trevi Fountain and the Pantheon, the hotel was designed by Spanish architect Patricia Urquiola, with 96 serene, modern guest rooms and suites (the best ones have their own terraces), an open-kitchen trattoria and bar, a rooftop terrace with prime views and a destination spa inspired by the ancient Roman baths (did you know "spa" comes from the Latin "salvus per aquam," or "health through water"?).
  • EAT/DRINK: I was surprised to discover an authentic Roman restaurant with excellent service on one of Rome's most touristed squares—facing the Pantheon. Ristorante Fortunato al Pantheon is a great place to have in your back pocket for a delicious meal during a busy day of sight-seeing.
  • SHOP: I always come home (from any trip) with a suitcase full of ceramics, and Flake's Arredo in Trastevere is one of my favorite places to stock up; they also have fun gifts for the home.
  • SEE/DO: The Indagare Ambassadors recently discovered a new highlight in Rome in Palazzo Colonna, "one of the oldest and largest private palaces in the city," writes Trey Ross. "And if you feel like playing Audrey Hepburn or Gregory Peck for the day? The ending scene from Roman Holiday was shot at the gallery." Read more here.

Explore the Indagare Guide to Italy for expert travel advice, itinerary ideas and hotel, restaurant and activity recommendations. Plus: Contact your Indagare Trip Designer or Indagare, if you are not yet a member, to start planning a trip.

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