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5-Day VIP Italy Itinerary — Rome & Florence
Italy's two most essential cities, connected by high-speed train through the heart of the country. This five-day private itinerary begins in Rome, where skip-the-line access and expert guides open the Colosseum, the Vatican Museums, and the secret corners that most visitors never find. Then it carries you north to Florence, where the Renaissance comes alive in the Uffizi, the Accademia, and the Chianti vineyards just beyond the city walls. Every transfer is private, every museum entrance is pre-reserved, and your dedicated team ensures the only thing you need to think about is where to have dinner.
Your private driver meets you at Rome's airport and delivers you to your hotel in the historic center. After settling in, the evening belongs to Rome at twilight. A guided walking tour takes you through the illuminated heart of the city — the Trevi Fountain shimmering without the daytime crowds, the Pantheon's ancient dome glowing under soft light, and Piazza Navona's Baroque fountains mirrored in the darkness. Your guide weaves together two thousand years of stories as you walk streets that emperors, artists, and pilgrims have worn smooth. It's the perfect introduction to the Eternal City.
A day that covers Rome's greatest monuments with none of the hassle. Morning begins with skip-the-line entry to the Colosseum, where your licensed guide brings the gladiatorial arena to life — the mechanics beneath the floor, the spectacle in the stands, the engineering that still amazes architects today. You continue through the Roman Forum and Palatine Hill, tracing the footsteps of senators and emperors. After lunch at leisure, the afternoon belongs to the Vatican: priority access to the Museums, the Gallery of Maps, the Raphael Rooms, and the Sistine Chapel — Michelangelo's ceiling seen without being rushed. A reserved passage leads directly into St. Peter's Basilica. Your driver returns you to the hotel as the Roman sky turns gold.
Morning transfer to Roma Termini, where a first-class high-speed train whisks you to Florence in under ninety minutes. Your Florentine driver meets you at Santa Maria Novella station and delivers you to your hotel — likely with views of the Duomo or the Arno. After settling in, the afternoon belongs to the Accademia Gallery, where Michelangelo's David stands in person far more powerful than any photograph suggests. From there, your guide leads you on a walking tour through Florence's historic center: the Duomo and Baptistery, Ponte Vecchio's goldsmith shops, Piazza della Signoria's open-air sculpture gallery, and the narrow streets where Dante, Machiavelli, and the Medici once walked.
Morning at the Uffizi — skip-the-line entry and a private guide who knows exactly which rooms to linger in and which to move through quickly. Botticelli's Birth of Venus and Primavera, Caravaggio's dramatic chiaroscuro, Leonardo's unfinished Adoration — centuries of artistic genius concentrated in a single building along the Arno. After the galleries, the landscape changes entirely. Your private driver takes you into the Chianti hills for an afternoon of Tuscan wine tasting at a carefully selected estate. Rolling vineyards, centuries-old cellars, and wines you can't find outside of Italy, paired with local cheeses, cured meats, and olive oil pressed from trees older than the farmhouse. You return to Florence as the sun sets over the terracotta rooftops.
Your final morning offers one last Florentine treasure. The Pitti Palace — the Medici family's grand residence — houses the Palatine Gallery, where Raphael, Titian, and Rubens hang in ornate rooms that feel more like a royal apartment than a museum. Behind the palace, the Boboli Gardens stretch across the hillside: Renaissance landscaping at its finest, with grottoes, fountains, and panoramic views across Florence. After the gardens, a final passeggiata — perhaps a last gelato, a leather shop visit, or simply sitting in a piazza watching the city move around you. Your private driver handles the transfer to the airport or station. Italy stays with you long after the flight home.
Five days across Italy's two most culturally rich cities. From the Colosseum and Vatican in Rome to the Uffizi and Chianti vineyards in Florence, every day is privately guided with skip-the-line access, luxury transportation, and curated experiences that go beyond the obvious. A high-speed train connects the two cities, and your dedicated team handles every reservation, transfer, and detail along the way.
5-Day VIP Italy Itinerary — Rome & Florence
