An Artful Italian Escape: A Journey Through Culture, Cuisine & Creativity

At TL365, we love showcasing the expertise of our travel advisors, who craft seamless, well-balanced itineraries tailored to every traveler’s desires. This exquisite Italian journey was designed by Jeanne Langlo, blending world-class art, immersive cultural experiences, and indulgent culinary moments. If you dream of Italy as a masterpiece—where Renaissance frescos meet plates of handmade pasta and ancient ruins whisper their stories—this itinerary offers the perfect blend of art, culture, and cuisine.

Day 1: Arrival in Rome – A Walk Through the Centuries

Your flight touches down in Rome and a private transfer whisks you to Hotel Virgilio, your home for the next three nights. Shake off jet lag with a slow, deliberate walk through the Centro Storico, where every piazza feels like an open-air museum. Make your way to the Pantheon, its vast dome an engineering marvel, before tossing a coin into the Trevi Fountain—a timeless ritual for those who wish to return to the Eternal City. As the sun sets, indulge in cacio e pepe at a tucked-away trattoria, where Roman tradition lives on in every twirl of pasta.

Day 2: The Soul of Rome – Ancient Wonders & Bohemian Corners

Start your morning in Trastevere, where ivy-clad buildings frame cobblestone streets. Visit the Basilica of Santa Maria in Trastevere, its golden mosaics glowing in the morning light, before wandering through the neighborhood’s artisan boutiques. Then, step into antiquity at the Colosseum and Roman Forum, where emperors once walked. For lunch, head to Testaccio, Rome’s historic food district, and sample supplì (fried rice balls) from a local market stall. As evening falls, sip a Negroni at a hidden rooftop bar, gazing over the city’s warm-hued skyline. 

Day 3: Vatican Grandeur & Local Delights

Today, you stand beneath Michelangelo’s Sistine Chapel, absorbing the breathtaking frescoes that changed the course of art history. Climb to the top of St. Peter’s Basilica for an unrivaled view of Rome, then reward yourself with a slice of pizza bianca from Forno Campo de’ Fiori. The afternoon calls for a deep dive into Galleria Borghese, where Bernini’s sculptures seem almost alive. Cap off your last night in Rome with a carbonara dinner in Monti, the city’s most stylish and intimate neighborhood. 

Day 4: Florence Beckons – Renaissance Reverie

Board a high-speed train to Florence, watching the Italian countryside unfold through your window. Rolling vineyards and charming hilltop towns pass by, each one a glimpse into Tuscany’s timeless beauty. Arrive in Florence and settle into your accommodations before spending the afternoon strolling through the city’s historic streets, crossing an iconic bridge lined with artisan shops. As the sun sets, take in panoramic views from a scenic overlook before indulging in a classic Tuscan dinner, complete with a perfectly paired regional wine.

Day 5: Michelangelo’s Masterpiece & Artisan Secrets

This morning, you skip the line at the Accademia Gallery, stepping into the presence of Michelangelo’s David—every sinew and muscle a testament to genius. Inspired, explore San Lorenzo Market, where leather artisans craft timeless pieces. Spend the afternoon at Santa Maria Novella Pharmacy, where monks have blended perfumes and elixirs since 1221. For dinner, let a truffle-tasting menu at a local enoteca immerse you in Tuscany’s earthy flavors.

Day 6: The Duomo & Florence’s Hidden Corners

This morning, your Duomo Express Tour includes a climb to Brunelleschi’s Dome—a physical and artistic feat rolled into one. Afterward, explore Oltrarno, Florence’s quieter, bohemian quarter, where artisans hammer out gold filigree and hand-bind books in centuries-old workshops. As dusk falls, slip into the cozy embrace of a vin santo and cantucci tasting, celebrating the simple sweetness of Tuscan life. 

Day 7-10: “On Your Own” – Tuscany’s Culinary & Cultural Heart

With a rental car in hand, you’re free to explore Tuscany at your own pace. Here’s how to make the most of it: 

• Pienza & Pecorino – Meander through Pienza, a town designed as the “ideal city” of the Renaissance. Sample aged pecorino cheese, best paired with a glass of local Brunello di Montalcino. 

• Montepulciano & Wine Caves – Descend into ancient cellars for a private wine tasting, where oak barrels line centuries-old vaults. 

• Siena & Its Contradas – Step into the world of the Palio, exploring the neighborhoods that fiercely compete in the world’s most thrilling horse race. 

• San Gimignano & Saffron Gelato – Wander the medieval towers of San Gimignano, stopping for the world’s best saffron-infused gelato at Gelateria Dondoli.

Day 11: To the Coast – Sorrento’s Limoncello Kiss

After returning the rental car, you step aboard a sleek high-speed train, settling in as the landscape shifts from rolling countryside to dramatic coastal vistas. Hilltop villages and ancient ruins flash by, each hinting at the rich history ahead. Arriving in Naples, a private transfer whisks you toward Sorrento, where the scent of lemon groves lingers in the warm air. From your terrace, a spritz in hand, you take in the shimmering Bay of Naples, knowing that the best of the Amalfi Coast awaits.

Day 12-15: Amalfi’s Coastal Treasures

From Sorrento, you can embark on some of Italy’s most stunning adventures: 

• Positano’s Cliffside Beauty – Wander the pastel-hued streets of Positano, where staircases lead to secret boutiques and sun-drenched cafés. 

• Capri’s Timeless Glamour – Take a boat to Capri, where the Blue Grotto shimmers like a sapphire and the Garden of Augustus offers views worthy of emperors. 

• Ravello’s Enchanted Villas – Step into a fairy tale at Villa Cimbrone, where gardens spill over into the sky. 

• Limoncello & Cooking Class – Learn the art of handmade gnocchi and sip limoncello straight from the source. 

Day 16: A Roman Farewell

A private transfer winds through the lively streets of Naples, delivering you to the station just as the evening sky deepens. You board a sleek high-speed train, watching the city lights flicker past as you journey toward Rome. The hum of travel lulls you into reflection—memories of sun-drenched coastlines, ancient ruins, and indulgent meals filling your thoughts. Upon arrival, your hotel near the airport offers a quiet retreat, a peaceful pause before the journey home. 

Day 17: Arrivederci, Italia

With one last espresso, you board your flight, carrying home not just memories, but the taste of truffles, the glow of frescoed ceilings, and the echo of ancient streets beneath your feet. 

Inspired to Craft Your Own Italian Masterpiece?

From Michelangelo’s Florence to Capri’s shimmering coastline, Italy is best experienced through its art, flavors, and stories. Let TL365’s expert advisors—like Jeanne Langlo—design your dream itinerary, where every stop is a brushstroke on your perfect Italian canvas. Contact us today to begin your journey!