Italy has been part of my life since I was 17, when my mother moved from London to live in Florence to manage a shoe company. I ended up studying there: learning Italian culture, taking art classes at the Uffizi Gallery, and paying my way as the “British DJ” in a basement disco. My family bought a small pensione (Italian boarding house) near the train station and my love for the country and Florence was ignited. Subsequent hotel jobs in Rome and Sardinia solidified that connection until today. It’s a love affair for life with the architecture, the food, the design, the creativity, and the absolute pervasive craziness of the Italian people.

Stay

Hotel Lungarno
Open since 1967 and recently renovated, this quirky 64-room hotel belonging to the Ferragamo family with interiors by Michele Bönan sits on the Arno river with spectacular views of the Ponte Vecchio. Watch the river activity from the breakfast room (or a river view room, a must) with steaming aromatic coffee and homemade brioche, or from the terrace at aperitivo time with an Aperol or white peach Bellini—it doesn’t get much better.

Four Seasons Hotel Firenze
With 72 rooms and 44 suites, and a 10-minute walk from the Duomo, the hotel resides in the 15th-century Palazzo della Gherardesca and a 16th-century former convent and boasts a park-like setting of 11 acres. This is an extraordinary hotel that took some 10 years to realize and, rather than mention the great spa and F&B, seek out my dear friend, the illustrious, elegant, and mischievous GM Patrizio Cipollini, who will tell you everything you need to know about Florence (and elsewhere). It’s a unique hotel in this precious city.

Castel Monastero
About 50 miles from Florence and 17 from Siena, bordering Chianti, this village is the absolute Tuscan countryside retreat or bolthole, especially if you’re attending the Palio di Siena horse race (highly recommended and a feature article in its own right). With 360-degree views of the rolling hills and adjacent vineyards, this spectacular property has one of the finest and most comprehensive spas and wellness programs in Italy, along with its own piazza and gorgeous church if you feel like renewing vows or being meditative (or praying, for that matter).

Eat

Osteria del Cinghiale Bianco
This osteria delivers the traditional Tuscan salumi and crostini, wild boar (that’s the cinghiale in the name) in several ways, tasty pasta, and is heavy on meat. But just as important is the coziness of the space and the friendliness of the staff, including owner Massimo Masselli. The welcome is always warm, and I feel like I’m going home.

Il Mercato Centrale
In 2015, the central market in San Lorenzo was renovated, adding 32,000 square feet of restaurant space (think an amazing Italian food court predating Eataly), tasting stands, a cooking school, and shops. Whenever I’m in Florence, it’s here that I buy my 4.5 pounds of fresh Parmesan and Tuscan truffle salami to take home. On the ground floor, hidden in a corner with the various food vendors is Da Nerbone—a place to visit for only one reason: the workmen’s staple sandwich of lampredotto (braised beef) and salsa verde bagnato (a green garlic salsa) in a chewy panini for about $3.50.

Buca Lapi
The oldest restaurant in Florence, opened in 1880, is in the basement of the Palazzo Antinori. Without a doubt, it serves the best dry-aged Florentine steak in town, to be eaten medium rare. Don’t eat too much during the daytime if you’re coming here for dinner. You could sample a fresh artichoke salad with Parmigiano beforehand, but go easy.

Il Canto del Maggio
Family run by Simona and Qui Qui, this wonderful farm-to-table osteria (complete with apartments to stay in and a pool) an hour or so from Florence is the real deal. A set menu is offered based around what’s grown on the farm and in the orchard. Tuscany is famous for its vegetables, and at Canto del Maggio, they’re meant to be savored. On the website, there’s a quote from Dorothy in the Wizard of Oz, which says “no place like home,” and this sentiment shows up in the care and love shown toward the homegrown produce.

Vivoli
At college in Florence in the ’70s, Vivoli was at least a twice a week event, and today the ice cream in this gelateria is as good as ever, with artisanal concoctions that are often more mousse-like in texture than your standard gelato.

Shop

Cellerini
Handmade in Florence, this beautiful leather goods store on Via del Sole is still run by the Cellerini family. Exquisite skins, meticulous workmanship, and interesting personal customization to their products continues to bring success after more than 30 years in business.

Space and the Mall
The Prada outlet is called Space and is in Montevarchi, about a 45-minute drive from Florence. It showcases a huge selection of everything for men and women at half the price or less. Then there’s the Mall in Leccio (also about 45 minutes from Florence); every great Italian brand or Italian-owned brand is there. Go early in the morning or slightly offseason, as it gets packed.

Umberto Chiappe
This men’s clothing store on Borgo San Jacopo just across the Ponte Vecchio makes the best linen shirts ever (reasonably priced, too), as well as terrific cotton pants and jeans. My annual visit there is to stock up for the Southeast Asian weather. If you go, ask for the owner, Massimo. When you’re done, cruise the street for shoes, cashmere, wool, bags, etc. It’s a great street.

Officina Profumo-Farmaceutica di Santa Maria Novella
Founded in 1612, a visit to this famous and iconic establishment near the main station is a sensory experience. From ancient preparations, extracts and essences, fragrances, cosmetics, and even dog and cat products, this architecturally striking building should be on any must-see list.

Todo Modo
This old yet modern book shop, café, and theater sells and restores books, offers food and drink, and puts on all types of shows. It has a good selection of books in English, too, the perfect place to get lost while browsing.