A Gary Janetti and Brad Goreski-Approved Italy Itinerary

Touch down in the Eternal City knowing everything’s been handled—SmartFlyer has partnered with trusted Italy-based partners to arrange a VIP greeter awaiting your arrival to whisk you through immigration, fast-track your luggage, and deliver you seamlessly to your private car. Within the hour, you’ll be pulling up to Bulgari Hotel Roma, a temple of Italian glamour where contemporary design meets the brand’s storied heritage. Settle into your suite, complete with marble bathrooms and the signature Bulgari touches (think: high-tech rooms including every Dyson product you can imagine) that’ll have you feeling right at home.

Ease into the evening with an aperitivo at La Terrazza, the hotel’s crown jewel overlooking Piazza Augusto Imperatore. Picture a chilled Negroni, the hum of surrounding Roman rooftops, and golden light bouncing off ancient ruins in the distance. When you’re ready to retire for dinner, homemade pasta awaits, whether you opt for Rocco Ristorante, Taverna Trilussa, or Pierluigi. Your Roman holiday has officially begun.

Start slow with breakfast in bed or beneath the dramatic arches of Il Caffè, Bulgari’s own chic dining room. (Editor’s Note: Dear reader, we’ll pretend like this wasn’t the part where Gary went to Starbucks). With only a few hours left in the city, sneak in a power lunch at Dal Bolognese, wander Via Condotti for a dose of retail therapy, or slip into a gallery before your driver whisks you to Roma Termini Station. VIP greeters will handle your bags and fast-track you to your first-class seats aboard Italo, Italy’s sleek high-speed train.

In under two hours, Florence greets you with Renaissance charm. Another SmartFlyer-arranged welcome is on deck to bring you from the train platform to Collegio alla Querce, an Auberge Resort Collection, a property that’s equal parts historic monastery and modern design sanctuary. Take in the attention to detail infused into every corner of your stunning signature suite, which just so happens to boast views of the Duomo. Freshen up, then head into town for dinner at Trattoria Cammillo—an old-school Florentine favorite where the bistecca alla fiorentina and the chocolate torte are non-negotiables.

Wake up in your suite surrounded by olive groves and terracotta rooftops. Start the morning slowly—savor a cappuccino (or, in Gary’s case, a meticulously concocted mocha) on your terrace before drifting down to the pool, where sun-dappled loungers and the scent of blooming jasmine set the tone for a day of soaking up dolce far niente.

Indulge in a treatment at the spa—perhaps a rosemary-infused massage or a restorative soak before returning back to lounge in the sun. A light poolside lunch calls for Cafe Focolare‘s prosciutto starter, the panzanella salad, the margherita and patate e tartufo pizzas. Obviously, this moment will warrant gelato for dessert.

As evening falls, savor the ephemeral high of a sun-kissed post-pool shower. Take your time getting ready for dinner, but know that La Gamella beckons. Here, every dish feels like a love letter to Tuscany, from vongole to grilled lamb chops kissed by local herbs. To cap off the night, order the off-menu dessert, the Biancomagiare—a traditional Sicilian almond milk pudding–before sipping a digestivo beneath a canopy of stars.

This morning, after savoring breakfast (don’t sleep on the homemade pastries at Collegio!), it’s time to head into town. Spend the morning meandering Florence’s cobblestone streets at your own pace. Whether you’re hunting for artisan leather goods or picking out new porcelain dishes at Ginori’s flagship store, the walkable city has a way of feeling like a real-life Renaissance painting. But we can’t have you wandering around on your own for too long—in typical SmartFlyer fashion, it’s time to link up with a local who can unlock otherwise closed doors.

Your time with your local guide begins at the Medici Chapels, where opulent mausoleums and Michelangelo’s marble masterpieces whisper secrets of Florence’s most powerful family. In partnership with our local partners at N2S Italia, we’ve scored you exclusive access to a private viewing of the chapel; be sure to soak up the sanctity of being solo in such a special place. Then, as golden hour bathes the city in light, your guide will whisk you off to board a private wooden barchetto for an Arno River cruise. Sip prosecco as you glide under Ponte Vecchio, the skyline glowing in soft pinks and golds. End the night at Atelier De Nerli, an intimate spot beloved by locals for its inventive twist on Tuscan classics.

Bid farewell to Florence with a final breakfast at Collegio’s garden terrace before your SmartFlyer-arranged driver whisks you back to the train station. First-class seats, a smooth ride, and by mid-afternoon, you’re back in Rome—this time for a deeper dive. Check into your suite back at the Bulgari Roma and maybe sneak down to the spa for a thermal ritual before the evening begins.

Start with an aperitivo (because when in Rome, always aperitivo!) back at La Terrazza, then get ready to make a little detour before heading to dinner. We’ve sent a vintage Alfa Romeo for a little cruise around town before making your way to Trattoria al Moro, a gem just a stone’s throw from the Trevi Fountain. Here, you can expect old-world charm meets serious culinary chops with a crowd of predominantly locals. Order the spaghetti al Moro, the slightly lighter cousin to carbonara. Don’t miss out on a little tourist moment by stopping at the Trevi to make your wish before ending the evening.

This morning, it’s time to head back to Fiumicino for wheels up on a quick ITA Airways hop to Palermo. From the tarmac to your suite at Villa Igiea, a Rocco Forte Hotel every detail is seamless, thanks to SmartFlyer amenities like early check-in, upgrade based on availability, daily breakfast for two, and a resort credit. Settle into your jaw-dropping suite—we love the Donna Franca Suite or Tower Suite—and enjoy the pleasures of indoor-outdoor living thanks to multiple balconies and terraces.

Perched above the Tyrrhenian Sea, this Rocco Forte jewel is the definition of grand Sicilian elegance—think frescoed salons, sweeping terraces, and a pool that practically begs you to cancel plans. But…plans you have. After settling in, slip into your best linens and head to Osteria dei Vespri, a Palermo institution serving inventive takes on Sicilian classics in a historic palazzo setting. Expect bright citrus notes, just-caught seafood, and desserts that turn, “I’ll just have a bite” into a lie not even worth uttering.

Today, after luxuriating in a slow breakfast on Villa Igiea’s stunning terrace, you’re trading Palermo’s city streets for soft white sand at Lidó Addaura, Palermo’s most polished beach club. With your loungers reserved and an umbrella perfectly positioned, the day is yours to bask, swim, and sip chilled rosé with toes in the sand. Break for a lunch of grilled swordfish and caponata, then linger just a little longer—because Sicilian afternoons were made for languor.

Back at Villa Igiea, freshen up for dinner at Florio back at the hotel, where chef Fulvio Pierangelini has designed a  menu is inspired by his philosophy of simplicity, generosity, and ultimate quality. This is real cuisine, sincere and natural. The tasting menu here is a stunner, especially when paired with a glass (or two!) of Etna Rosso as the Mediterranean hums outside.

There are boat days, and then there are yacht days. Today, you’ll cruise the Palermitan coast aboard the latter, exploring secret coves, sea caves, and waters so clear they beg for a plunge. Between swims, savor a spread of Sicilian bites and crisp local wines as the sky melts from gold to blush. This is la dolce vita at its peak.

Return to shore just in time for a late dinner—if you have room—back at Isgrò, a fish market and restaurant, or alternatively, a tucked-away trattoria your concierge has on speed dial. Either way, expect fresh seafood, flickering candlelight, and that deep contentment only a day spent in salt air can bring.

Your final full day calls for a cultural deep dive. We’ve paired you with one of Palermo’s most legendary guides to take you through the foodie highlights of this coastal city. She’ll having you climbing into into an Ape Calessino (a darling three-wheeled car) for a guided whirl through Palermo’s Arab-Norman jewels, from the glittering Palatine Chapel to the rooftop of Santa Caterina with its jaw-dropping panoramas.

Then, trade monuments for markets as you nibble your way through the city’s street food icons: arancine, sfincione, panelle, and of course, a cannolo that will ruin you for all others. For your final evening,  with a dinner at Ciccio Passami l’Olio, a local favorite where seasonal simplicity steals the show. Toast with a final glass of grillo and let the flavors—and memories—linger.

Savor one last cappuccino on the terrace at Villa Igiea before your driver escorts you to Palermo airport for a smooth SmartFlyer departure experience, complete with VIP assistance and lounge access. As you board your flight, it hits you: this wasn’t just a trip. It was another chapter of your love affair with Italy—and it’s only a matter of time before you’re back to write the next one.