Italy

Nobody plans “a trip to Italy.” You plan a coast trip, a wine trip, a cities trip, a lakes trip — or, with enough days, a route that strings two of them together without spending half the vacation in transit. That’s the real work of an Italy itinerary: choosing which Italy this trip is for.

The shapes I plan most

The coast. Positano for charm, Amalfi town for history, Ravello for quiet — the Amalfi Coast earns its reputation for romance and scenery, and it rewards travelers who settle into one base rather than hopping nightly. Fresh seafood, limoncello, slow afternoons.

Wine country. Tuscany and Piedmont are the two anchors. Tuscany means Chianti vineyard lunches, Brunello in Montalcino, and the hilltop villages of the Val d’Orcia; Piedmont means Barolo, Barbaresco, and truffle season. The best versions pair a countryside estate with a nearby city — Florence with Tuscany is the classic — and move slowly on purpose.

The lakes. Como is the elegant one; Garda is the more historic, more affordable one. Both are at their best as summer trips, and both suit multigenerational groups: the older generation gets the terrace, the kids get the lake.

Venice as a gateway. Venice is extraordinary — and it’s also the front door to Prosecco country, Lake Garda, and the Dolomites, with Slovenia, Croatia, and Austria within reach. If you have ten days or more, starting in Venice and moving onward makes a far better trip than treating it as a two-day finale.

Why book Italy through an advisor

Italy in high season is a supply problem: the well-located hotels, the drivers worth hiring, the vineyard visits that aren’t tour-bus operations. Booking through my hotel partnerships regularly adds breakfast, upgrades when available, and property credits — at the same rate you’d pay booking alone. And for milestone trips — anniversaries, big birthdays, a whole family traveling together — I build the itinerary around the people, not the checklist.