La Dolce Vita, Perfected

Arrive in Rome and check into Chapter Roma—with early check-in as one of the perks of booking through a Fora Advisor—then head out for an easy first taste of the city with a hop-on, hop-off Big Bus tour. It’s how my family loves to start in a new place: You cover so much ground without having to walk it all after a long travel day, and it’s the perfect way to get your bearings.

If you happen to arrive early and still have energy to spare, add a short guided stroll through Trastevere or Campo de’ Fiori for a more personal introduction to Roman life. And whatever you do, make sure your first plate of cacio e pepe finds its way to the table—just pasta, Pecorino Romano, black pepper, and a little magic from the starchy pasta water. Delicious.

The next day is all about ancient Rome, starting with a private Colosseum tour that includes exclusive arena floor access through the Gladiators’ Gate, followed by time at the Roman Forum and Palatine Hill to wander the ruins that once shaped an empire.

Your final day is dedicated to the Vatican, where skip-the-line access and an expert guide lead you through the Vatican Museums (including the Raphael Rooms and the ancient Laocoön), the awe-inspiring Sistine Chapel, and the grandeur of St. Peter’s Basilica. End your Roman adventure at Castel Sant’Angelo, where you can linger over sweeping views of the Tiber and the city—the perfect spot to pause, reflect, and say your own heartfelt goodbye to the Eternal City.

Make your way south to the stunning Amalfi Coast, where the pace shifts to the laid-back elegance of seaside life. Arrive in Praiano and settle into the serene luxury of Casa Angelina, perched high above the sea, before spending the afternoon with a spritz in hand, soaking in those endless views.

The next morning, set out on a private boat to the glamorous island of Capri, cruising past dramatic cliffs and sea caves, with time to swim in turquoise coves, circle the iconic Faraglioni rocks, or dock for a chic lunch in town—prosecco and sea breeze included. It’s the kind of day my family and I will want to relive over and over, forever etched in memory for its beauty, joy, and pure magic. Be sure to try a plate of spaghetti alle vongole (spaghetti with clams), a coastal classic that tastes like sunshine and sea air in every bite.

On your final day along the coast, take the scenic drive to Ravello, winding past pastel-hued towns and jaw-dropping cliffs. Perched high above the water, Ravello’s elegant gardens and sweeping vistas invite you to linger over a long lunch before returning to Praiano to watch the evening light dance across the sea.

Head north to the rolling hills of Tuscany, trading the coast for the golden countryside. Arrive in the charming hill town of Cortona and settle into Monastero di Cortona, your luxurious base for the next few days. Spend your first evening with a slow stroll through cobbled streets, followed by dinner in the piazza as you ease into the unhurried rhythm of Tuscan life.

The following day, set out to explore some of southern Tuscany’s most picturesque villages: Montepulciano, with its Renaissance architecture and world-class Vino Nobile wines; Pienza, a UNESCO-listed gem famous for its pecorino cheese, sweeping Val d’Orcia views, and romantic streets named after love, like Via dell’Amore (Street of Love) and Via del Bacio (Street of the Kiss); and perhaps Montalcino or a countryside estate for a late-afternoon tasting before returning to Cortona for dinner.

On your final day in the region, immerse yourself in a private wine experience, visiting acclaimed wineries producing the bold blends that redefined Tuscan reds. With guided tastings, behind-the-scenes cellar tours, and a long, lazy lunch paired with local wines, it’s the perfect way to explore the real Tuscany.

Make your way to Florence, the cradle of the Renaissance, for a jam-packed two days of art, history, and unforgettable views. After checking in at the stylish Gallery Hotel Art, spend the afternoon wandering across the Ponte Vecchio, pausing in Piazza della Signoria, and maybe ducking into a café for an espresso while you people-watch. If there’s time, stop by the San Lorenzo leather market—touristy, but worth it for the buttery-soft bags and jackets Florence is known for.

As evening falls, enjoy dinner steps from the Duomo at Cantina De’ Pucci, a cozy spot with classic Tuscan dishes and a historic wine window—one of the quirky little Florence traditions I can help you seek out all over the city. If you’re up for it, try bistecca alla fiorentina—a thick-cut T-bone that’s a true local tradition.

The next day, join a guided walking tour that takes in Florence’s icons: the Accademia to see Michelangelo’s David, the Uffizi Gallery, and even a climb to the top of the Duomo for breathtaking views. Pause for a gelato (Florence claims to have invented it), then head up to Piazzale Michelangelo for a sunset over the rooftops—a view you’ll carry with you long after the trip ends.

Say arrivederci to Florence as you board the train to Venice—a scenic, comfortable ride into one of Italy’s most iconic cities. After checking in at Palazzina Grassi, settle into the slower rhythm of life on the canals. Spend your first evening wandering quiet alleyways, crossing arched bridges, and enjoying dinner in a tucked-away campo where locals linger over plates of fresh seafood.

The next day, step into the heart of Venice with a private tour of St. Mark’s Basilica and the Doge’s Palace, skipping the lines and diving straight into the city’s political intrigue and artistic treasures. Wander through grand halls, cross the Bridge of Sighs, and stand in awe beneath glittering golden mosaics. In the late afternoon, glide through the quieter canals on a private gondola ride—a peaceful, timeless way to see the city from the water. As night falls, consider a canal-view dinner at Osteria alle Testiere or Lineadombra, or toast your final Venetian evening with cocktails at Terrazza Danieli while the city sparkles around you.

Trade Venice’s winding canals for the crisp air and alpine elegance of Lake Como. Whether you arrive by train and driver or private transfer, the journey north unfolds into a landscape of shimmering water framed by dramatic mountains. Arrive in Menaggio and check in at the Grand Hotel Victoria, where refined comfort meets panoramic lake views. Spend the evening unwinding by the water and soaking in the quiet charm of this lakeside escape.

The next day, explore the lake by private boat—the most unforgettable way to take in its elegant villas, lush gardens, and postcard-perfect villages. Cruise past Villa del Balbianello and Villa Carlotta, with time to stop in Bellagio or Varenna for a stroll and gelato. Your captain can tailor the day to your style, whether that means history, gardens, or simply drifting in the sun.

On your final morning, visit the elegant town of Como, riding the funicular up to Brunate for sweeping views, or lingering lakeside to explore charming streets, boutiques, and the impressive Duomo. If time allows, stop at one last villa—perhaps Carlotta or Melzi—for a peaceful garden walk before beginning the final leg of your journey.

Arrive in Milan and check in at Speronari Suites, just steps from the Duomo. In the afternoon, see Leonardo da Vinci’s Last Supper—an intimate, moving finale to your art-filled journey through Italy. As evening approaches, head to the Duomo rooftop for sweeping sunset views over the city’s iconic spires, then toast your final night with an aperitivo and a plate of risotto alla milanese, the city’s saffron-infused signature dish, at Ristorante Galleria, an elegant spot tucked inside the stunning Galleria Vittorio Emanuele II.

The next morning, enjoy one last Italian breakfast before making your way to the airport—bags full, heart fuller. Grazie, Italia.