This itinerary is for the traveler who wants Italy done right the first time. For the couple celebrating something meaningful. For the first timer who wants the icons, but doesn’t want to feel like they’re running a marathon between them. For the traveler who values beautiful train rides, well located hotels, seamless transfers, and experiences that actually make the places come alive.
Day 1–2: Venice
You land in Venice and are met and transferred directly to your hotel no navigating vaporetto lines with luggage, no guessing games. Just arrival, handled. Venice is the perfect beginning. It’s romantic, walkable and cinematic. A thoughtfully placed hotel means you step outside and you’re already in it.
One morning, you join a small group food tour tasting your way through cicchetti, local wines, and tucked away corners you wouldn’t find alone. It’s the kind of experience that turns a city from beautiful to personal.
Day 3–4: Portofino & the Ligurian Coast
From Venice, you glide south by rail, a route that’s scenic, efficient, and far more enjoyable than airports. I plan these connections intentionally, minimizing stress while maximizing views. Portofino adds romance combined with nature to the itinerary. Here, you hike privately to San Fruttuoso, a hidden abbey reachable only by foot or boat. It’s dramatic, coastal and absolutely unforgettable.
Day 5–6: Rome
You arrive by train and are taken by private transport to your hotel.
Your hotel location makes it easy to explore on foot and that changes everything. You’re not commuting to the magic you’re staying in it. One evening, you join a pasta making class with gelato. It’s immersive without being overwhelming. Structured, but still fun. This is what I mean when I say balance.
Day 7–8: Florence (with Cinque Terre)
A quick, seamless train brings you to Florence, compact, artistic, endlessly walkable. From here, a day trip to Cinque Terre adds color and coastline without forcing a hotel change. This is intentional design to experience more, move less. Florence gives you Renaissance beauty. Cinque Terre gives you pastel villages clinging to cliffs.
Day 9–12: Positano & Capri
Then you head south.
Florence to Naples by high speed train, followed by a private transfer straight to your hotel in Positano, because the Amalfi Coast is not the place to wing logistics. This is where thoughtful planning makes the biggest difference. Positano is for slowing down. Long lunches. Sea views. Evenings that stretch. One day is dedicated to Capri with its dramatic cliffs, blue water, and that unmistakable Italian glamour. And because you’re not bouncing hotels every night, you actually get to enjoy it.
Departure
A private transfer back to Naples airport closes the loop no scrambling, no last-minute stress.
Why This Route Works for a First Trip to Italy
It moves logically from north to south. It blends icons with intimacy. It balances guided experiences with breathing room. It uses Italy’s rail network beautifully. It reduces friction at the right moments (arrivals, coastal transfers).
And perhaps most importantly, it feels adventurous without feeling exhausting. This isn’t “see everything Italy has to offer.” It’s get a taste in the right order, at the right pace.
If you’re dreaming of Italy and want it to feel seamless, connected, and deeply memorable, this is exactly the kind of trip I design. When you’re ready to turn an idea like this into your version of Italy, I’d love to plan it with you. Click here to get started!
