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La Dolce Vita

Immerse yourself in Italian-style luxury—from Sicily’s seaside retreats to Sorrento’s charming side streets, Rome’s grandeur to Tuscany’s vineyards.

Located in Montaione, a village in the province of Florence, Toscana Resort Castelfalfi contains a mountain golf course, clay tennis courts, two restaurants, a restored medieval village, a hotel, and working olive groves and vineyards.

Prior to embarking on our first transatlantic trip together, my husband and I had a series of negotiations before we determined where to go. Finally, we were able to agree on a few musts: a beautiful place to relax; a place where we could explore beaches, sweeping rural landscapes and bustling city streets; and, most important, a place to indulge in decadent cuisine. Ciao, Italy.

The first stop on our 12-day trip is Rocco Forte’s Verdura Resort (S.S. 115, Km 131, Sicily, +, a 6-year-old golf and spa resort in southern Sicily, set on the Mediterranean Sea near Sciacca, a historic port town. From the moment we step out of our rental car, memories of our long flight disappear. The salty sea air combined with striking ocean views, vibrant greenery and modern architecture is the perfect introduction to our vacation.

Before long, a golf cart transports us to our room, an impressive grand suite ($775 per night) that leads out to a double terrace with sea and golf-course views. An unexpected treat is the huge, gorgeous bathroom made out of pale stones, which overlooks another private patio and comes with its own daybed. After taking in the richly hued room’s offerings—including a selection of paperback mysteries by Sicilian writer Andrea Camilleri, prosecco on ice and fresh-baked Sicilian almond paste cookies—we relax on the four-poster bed to contemplate our luck, patio door wide open as the sea breeze gently blows in.

Our time at Verdura Resort is spent enjoying all it has to offer—activities range from golf on the seaside course to riding bicycles across the expansive property to authentic Italian cooking classes—plus an afternoon drive to Sciacca for exploring and lunch at the outstanding slow-food restaurant Hostaria del Vicolo (Vicolo Sammaritano, 10, Sciacca, + Here, we sample perfectly tender octopus caught right in the bay and dip homemade bread into rich local olive oil. Verdura Resort has four restaurants on-site, offering everything from a fresh and varied buffet breakfast at Buon Giorno to fine Mediterranean dining at Zagara. Our favorites, however, are Liolà, a friendly Sicilian trattoria serving rustic homemade pastas, salads and hearty mains; and Amare, a casual waterfront spot that specializes in fresh grilled fish and pizza baked in a wood oven.

The beautifully appointed rooms at the Grand Hotel Excelsior Vittoria in Sorrento contain a chic mix of antiques and modern furniture.

When not dining—rare, this is Italy, after all—we’re at the extensive spa. Situated around an open-air courtyard, there are four outdoor thalassotherapy pools with stunning views of the rolling landscape, a double-height hammam, a lap pool, a fitness studio and 11 treatment rooms. We spend one afternoon indulging in the Ritual for Couples ($360 for 90 minutes). The treatment includes a full-body rubdown and an energizing head massage, and concludes with an essential oil-infused bath with views of the Sicilian countryside.

After three relaxing days, we set off for our next adventure. A two-hour drive back to Falcone–Borsellino Airport in Palermo, a short Alitalia flight to Naples and an hourlong drive south along the coast eventually brings us to the Grand Hotel Excelsior Vittoria (Piazza Tasso, 34, Sorrento, +, the 181-year-old crown jewel of Sorrento. Set in the historic town center and surrounded by a grove of orange trees, the elegant hotel has been run by the Fiorentino family since 1834, as is evident in its undeniable character and impeccable service.

From the moment we arrive, we are treated like royalty by the experienced staff, namely, the head concierge, Antonio Galano Jr., who has been at the hotel for more than 40 years, his father having led the charge before him. The hotel is currently rolling out a renovation, and our base, room 549 ($1,352 per night), is one of the first to have been updated. The spacious deluxe suite is filled with a mix of old and new decor—blending antique furniture with modern black-and-white paintings, smooth wood floors, crisp white linens, hardcover design books and glossy new magazines—that reminds me of a tastefully appointed Manhattan apartment, albeit one with a huge terrace overlooking the Bay of Naples and Mount Vesuvius.

We spend our time wandering narrow streets and curvy back alleys, all lined with linen and leather stores; souvenir shops selling limoncello, coral jewelry and inlaid wood decor; and an array of trattorias, ristorantes and gelato stands. My favorite treat: scoops of organic hazelnut gelato at Momi (Corso Italia 127, Sorrento, + When we need a break, we relax at the hotel, either on our balcony with newspapers and cappuccinos or in one of the welcoming seating areas on the hotel’s beautifully manicured property.

A highlight has to be an afternoon spent at La Serra, the hotel’s spa, which offers a variety of treatments incorporating local citrus fruits and olive seeds, all in a calming greenhouse-style setting adjacent to the pool area. The experience begins with one of the best massages I’ve had in my life ($360 for 90 minutes, for two), performed on a heated table, followed by a fragrant hydrotherapeutic bath and herbal teas in the private garden of the treatment suite.

Not to be missed is the hotel’s incredible breakfast. Held in a large room with vaulted, painted ceilings and overlooking the sea, the generous buffet is presented in grand Italian style. Fresh baked goods mingle with every type of fruit imaginable; delicate eggs are made to order; and coffee is poured from a silver pitcher. A special dinner at the hotel’s Michelin-starred fine dining restaurant, Terrazza Bosquet, is equally impressive. Our mouths water over beautifully presented homemade seaweed pasta with Venus clams, sea urchins and chives; blue lobster served on a tartare of San Marzano tomatoes; and tender lamb chops in mushroom crumbs with pomegranate jelly, baby vegetables and star anise sauce. The wines—including a full-bodied 2008 Caprili Brunello di Montalcino—complement the food perfectly.

Next up on our journey: Rome! After a private car takes us to the Naples train station, we hop on a high-speed train and arrive in the Eternal City in less than two hours. A quick taxi ride from Termini station takes us to our home for the next two evenings, Rocco Forte’s elegant Hotel de Russie (Via del Babuino, 9, Rome, + Adjacent to the Piazza del Popolo and a short walk to all of the major historic sites—the Spanish Steps, Trevi Fountain, the Vatican, the Colosseum and more—the 88-room property is not only the perfect base for exploring the busy metropolis, but also a gorgeous respite.

Long known as a destination for aristocrats, movie stars and Russian royalty, the hotel has a classic exterior, with modern interiors executed in calming, muted shades. When not out exploring or relaxing in our room, an executive suite ($1,887 per night), we spend plenty of time in the hotel’s enchanted hidden garden, home to the storied Stravinskij Bar—known as one of the most exclusive meeting places in Rome—and Le Jardin de Russie Italian restaurant. We also spend time soaking in the turquoise-tiled baths at the spa, a truly soothing treat after walking around all day.

In a city filled with endless food options, it can be tough choosing just the right place. But we find perfection one night at Osteria da Fortunata (Via del Pellegrino, 11, Rome, +, a bustling neighborhood gem located 10-minutes away by taxi from the hotel. The aromas of garlic roasting and fresh tomatoes draw us in immediately, as does the sight of a woman, seated by the window, rolling out fresh pasta. Unlike many restaurants located in the city center, this one is filled mainly with locals, a sign that it’s the real deal. After finishing a delectable bowl of al dente pasta with spicy arrabiata sauce, my only regret is that we didn’t eat here for every meal.

Our last day in Rome is spent strolling around and taking in the undeniable beauty of the ancient city. Two streets of note, the superchic Via Borgognona and Via dei Condotti, remind me of NYC’s Fifth Avenue or L.A.’s Melrose Place. Tucked away behind the busy shopping street Corso Como and open only to pedestrians, they are lined with designer shops (Balenciaga, Gucci, Fendi) and beautiful cafes. We take a break from traditional Italian food with fresh salads and smoothies at Ginger (Via Borgognona, 43-44, Rome, + before checking out of the hotel. From there, we taxi over to Rome’s Fiumicino Airport, where we pick up a rental car—we heeded advice to avoid driving in the city center—en route to our final destination, Tuscany.

It’s nearly four hours before we arrive at the Toscana Resort Castelfalfi (Loc. Castelfalfi, Montaione, Florence, +, located in Montaione, about an hour southwest of Florence by car. It’s a unique property, an 800-year-old medieval hamlet that covers more than 2,700 acres of vineyards, olive groves, woods and lakes; since 2007 it has been in the process of being developed by TUI, a European-based tourism company. There are plans for a five-star, 120-room hotel, spa and restaurant to open in summer 2016, but we stayed in the charming 31-room La Tabaccaia (standard rooms from $224 per night, suites from $302 per night), which opened in 2013.

A few steps from La Tabaccaia is the Borgo, or ancient village, which contains a fully restored town with 12 boutiques, including Gelateria II, a new homemade ice cream shop; the castle, where a fine dining restaurant, La Rocca di Castelfalfi, opened in June 2014; and 48 apartments boasting off-the-charts Tuscan charm, some of which are available to purchase. Also walkable is Il Rosmarino restaurant (Via Castelfalfi, Montaione, Florence, +, opened in the summer of 2011, with a focus on locally sourced ingredients, a seasonal Tuscan menu and a warm, relaxed atmosphere. We ate most meals here during our time in the area.

We spend one day touring the impressive grounds, taking in views of the challenging golf course and getting glimpses of the 57 acres of vineyards (producing Chianti DOCG, Rosso Toscano IGT and an IGT red Tuscan wine) and extensive olive groves. We also take two daytrips. One to Florence, where we ogled Michelangelo’s “David” and the Duomo, and another to San Gimignano, a famous walled medieval town inhabited by artists selling their wares. Sprinkled among shops selling postcards and T-shirts are boutiques offering handmade scarves, beautiful leather shoes, hand-carved olive wood bowls and unique jewelry. Surprisingly, it’s in this small city where we both purchase our bigger-ticket souvenirs. I splurge on a navy blue leather motorcycle jacket, while my husband buys a gorgeous pair of hand-stitched oxfords.

Our final night in Italy is spent back at Il Rosmarino, where we linger over a bottle of Chianti and indulge in homemade bread and incredible local olive oil, letting the taste of the region and the experiences of the past two weeks sink in. We toast to the memories, to each other and, most important, to returning to this magical place again and again.