ICONIC ITALY

EXPLORE THE MOST ICONIC REGIONS IN NORTHERN ITALY

Trip Style: Explore

Including Milan, Cinque Terre, Tuscany, Florence, Siena & ROME

trip highlights

Italy has a way of making even an ordinary day feel memorable. A morning espresso in a neighborhood café, a train winding through the countryside, a long lunch at a family-run farm, or an evening passeggiata through a medieval town can become as memorable as the famous sights themselves.

Our 10-day Iconic Italy itinerary combines the places you came to Italy to see with the experiences that help you understand the country beyond its postcard images. Begin in Milan, then travel by train along the coast to the colorful villages of Cinque Terre and onward to Florence. From there, pick up a car and head into the Tuscan countryside, where you'll explore hilltop towns, stay in distinctive farmhouses, taste local olive oil and wine, and experience the agricultural traditions that have shaped the region for generations. Your journey concludes in Rome, where ancient history, art and everyday Italian life come together.

The route is designed to give you the best of both worlds: the freedom of independent travel without the burden of planning every detail yourself. We've mapped the route, selected the accommodations, arranged transportation and curated experiences along the way, while leaving you plenty of room to linger over lunch, wander down an unfamiliar street, or change your plans when you discover somewhere you want to stay a little longer.

And because this is a custom itinerary, the 10-day journey you see here is a starting point—not a fixed formula. Want more time in Tuscany? Add another night. Prefer to skip Rome? We can reshape the route. Want to add a cooking class, winery visit, or more time in the countryside? We'll build it around you.

Book our 10-day Iconic Italy itinerary with custom dates year-round, starting at $2,995 per person. See all inclusions, itinerary details and complete pricing in the drop-downs below.

why this trip?

Italy has no shortage of famous places. Florence, Cinque Terre, Tuscany, Rome and Milan are famous for good reason. But the most memorable Italian experiences often happen in the spaces between the headline attractions: a farm lunch beneath the olive trees, a small producer explaining how this year's harvest compares to last year's, a quiet village where you stop for coffee, or a farmhouse where the landscape becomes part of the experience.

That's why we've built Iconic Italy around both the places you want to see and the places that help you understand them.

You'll experience the grandeur of Florence and Rome, but you'll also have time in the Tuscan countryside. You'll walk the coastal villages of Cinque Terre, then trade the train for a car and follow winding roads through vineyards and olive groves. And rather than treating food as simply another thing to consume, you'll have opportunities to connect it to the land—from olive oil tasting at a Tuscan orchard to meals shaped by local and seasonal ingredients.

That connection between food, land and culture is deeply woven into Italian life. In fact, Italy's contemporary conversations around regenerative agriculture and the Slow Food movement are rooted in much older traditions of small-scale farming, biodiversity and seasonal production.

The result is a trip that gives you the icons but doesn't stop there.

With this self-guided Iconic Italy itinerary, we handle the architecture of the journey; you get to experience it your way. Your accommodations, transportation, key activities and local recommendations are arranged in advance, so you're not spending your vacation figuring out where to stay, how to get from one place to the next, or which restaurant reviews to trust.

That's the beauty of a well-designed self-guided journey: structure where it helps and freedom where it matters.

Italy rewards different ways of moving through it. In the cities and along the coast, train travel keeps things easy. You can settle into your seat, watch the landscape change outside the window and arrive in the heart of the next destination without worrying about traffic or parking. Once you reach Tuscany, having a car gives you a completely different kind of freedom. The countryside is where you'll find winding roads, hilltop towns, vineyards, olive groves and farmhouses that aren't always accessible by public transportation.

We've designed the route around that distinction—train where trains make the most sense, driving where having a car makes the journey better.

And of course, Italian food is inseparable from the landscape that produces it. On this journey, you'll have the opportunity to experience that relationship firsthand with an olive oil tasting and farm lunch at a Tuscan orchard, along with regional wines and local specialties throughout the trip. It's a small example of what we mean by traveling beyond the obvious. You're not simply tasting olive oil; you're seeing where it comes from, meeting the people who produce it, and experiencing the agricultural landscape behind something that might otherwise arrive on your table without a story.

Rather than defaulting to interchangeable hotels, we look for boutique accommodations, distinctive farmhouses and places with a sense of connection to their surroundings. You can stay with our boutique 3-star base package selections, or upgrade for a more luxurious experience. Every Iconic Italy journey can be adapted around your travel dates, interests, pace and priorities. Add nights, change the balance between cities and countryside, include additional food and wine experiences, or extend the journey beyond the route shown here.

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