ITALY — where every region feels like a different trip

WHY IT’S ON OUR RADAR

Everyone is going to Italy. Everyone has always been going to Italy. And honestly? The obsession is completely justified. Rome, Florence, Venice, the Amalfi Coast — these places are iconic for a reason, and seeing them in person still delivers. The Colosseum at golden hour. The Grand Canal at dusk. The view from above Positano. None of it is overhyped.

But here’s the thing: Italy is so much more than its greatest hits. And the travelers who come back the most satisfied are almost always the ones who went somewhere they didn’t expect to fall in love with. The hilltop towns of Umbria. The thermal seas of the Aeolian Islands. The truffle roads of Piedmont. The Maremma coast, where Hotel Il Pellicano — the original and most storied property in the Pellicano Hotels portfolio — has been setting the benchmark for Italian coastal elegance for decades, long before anyone needed an algorithm to tell them it was good.

Italy also happens to be one of the rare destinations that works equally well for every kind of traveler. Couples and honeymoons, milestone celebrations, solo trips, and multi-generational families — the country bends to whatever kind of trip you need it to be. Children who have no interest in museums will still stand inside the Colosseum completely speechless. That’s the kind of place this is.

AT A GLANCE

• The Vibe:

  • Timeless, layered, and better every time you go. Art, architecture, coastline, countryside, food culture — and somehow, it all still surprises you.

• Who It’s Perfect For:

  • Honeymooners, couples, families, and anyone who thinks they’ve already seen enough of Europe to be impressed.

• Time Well Spent:

  • 10–14 days if you want to move through multiple regions. 5–7 days if you’re committing to one area and doing it properly.

• When To Go:

  • High season: June–August & December–January (ski regions)

  • Shoulder season: April–May & September–October — the sweet spot for weather, crowds, and price.

• If You’re Into:

  • Art & architecture, food & wine, history, coastal scenery, or countryside estates.

THE LFTD TRAVEL PERSPECTIVE

The biggest mistake we see in Italy planning is the Grand Slam itinerary: Rome, Florence, Venice, and the Amalfi Coast — all in ten days. It sounds incredible on paper and exhausting in practice. You end up spending half your trip moving between cities, eating at tourist restaurants near your hotel because there’s no time to explore, and returning home having seen a lot but absorbed very little.

How we plan Italy depends entirely on who’s going and what they want. For couples or honeymooners, we often build around one city — Florence is the sweet spot — paired with a stint in Umbria at a property like Castello di Reschio, where you can slow down, eat well, and actually feel the countryside. For the coast, Porto Ercole and the Maremma are dramatically underrated compared to the Amalfi crowds. For those doing a longer multi-region trip, we map it so the travel days make sense and the transition points are interesting in themselves, not just logistics.

Italy is also genuinely exceptional for families — arguably one of the best family destinations in the world. Italians adore children, the food is never a problem, and the range of experiences that work across generations is unmatched. A cooking class, a truffle hunt, a boat day off the Aeolian Islands, a working vineyard — these land just as well for a curious child as they do for their grandparents. We build family Italy trips regularly, and they’re some of the most rewarding itineraries we put together.

WHERE WE’D SEND YOU

STAY

• collegio alla querce

• Hotel Il Pellicano, Porto Ercole

• Castello di Reschio, Umbria

• Rosewood Castiglion del Bosco, Tuscany

• Borgo Egnazia, Puglia

INDULGE

• Osteria Francescana in Modena — one of the most celebrated restaurants in the world, worth planning a trip around

• The unbothered lunch culture of Bologna, Italy’s unofficial food capital

• Small-producer wine tastings in Barolo and Barbaresco that never make travel magazine lists

• Hand-rolled pasta in a farmhouse kitchen in Emilia-Romagna

• Seafood the way it’s done in Sicily — simple, perfect, caught that morning

EXPERIENCE

• Private access to the Vatican before public opening hours — the difference is indescribable

• A boat-only village on the Amalfi Coast with no road access and no tourist crowds

• Sailing the Aeolian Islands on a private charter — volcanic islands, thermal waters, and almost no one else around

• Private guided Pompeii at dusk

• Shopping the Quadrilatero della Moda in Milan with someone who knows where Italians actually buy

You already know you want to go to Italy. Let’s make sure you do it in a way that actually lives up to it.