Destination Guide

Where to go in Italy for the first time

Italy is not one trip, it is a dozen. The Amalfi Coast and Tuscany could be different countries. The question is never really where to go in Italy, it is which Italy fits the trip you are dreaming of. Here is how I help clients choose, region by region, so the first trip is right and the second one is already forming.

Kay JonesTravel Advisor & Retreat Curator · Destination Guide · 6 min read

The pastel cliffside village of Positano tumbling down to a turquoise sea on the Amalfi Coast — Positano, on the Amalfi Coast. The Italy most people picture first.

The Amalfi Coast, for romance and drama

Cliffside villages, lemon groves, long lunches above the sea. The Amalfi Coast is the postcard, and it earns it. This is the choice for honeymoons, anniversaries, and anyone who wants beauty turned all the way up. It is also busy and vertical, so pacing matters. I build in boat days and quiet mornings so the glamour never tips into exhaustion.

Tuscany, for the slow, golden version

If the Amalfi Coast is a crescendo, Tuscany is a long exhale. Cypress-lined roads, hilltop towns, vineyards, and food that tastes like the place it came from. Come here to drive, to linger over wine, to stay in a converted farmhouse and do gloriously little. It is my pick for travelers who want Italy to slow them down rather than dazzle them.

Rolling Tuscan hills with a winding cypress-lined road at golden hour — Val d'Orcia, Tuscany. The Italy that teaches you to slow down.

The mistake first-timers make is trying to see all of Italy in ten days. The magic is in choosing one or two regions and letting them unfold.

The great cities, for art and appetite

Rome, Florence, Venice. History you can walk through, the best meal of your life around an unmarked corner, and museums that reorder what you thought you knew. A first trip often threads two cities together. My only rule is to leave room between the sights, because the unplanned hour, a piazza at dusk, a wine bar you did not mean to find, is usually the one you remember.

Early morning light on a quiet Venice canal with gondolas moored along the water — Venice at dawn, before the day crowds arrive. Timing is everything here.

The Italian Lakes, for elegant calm

Lake Como and its neighbors are grand and serene at once: villa gardens, mountain backdrops, and a refined, unhurried pace. This is Italy for travelers who want water and beauty without the heat and bustle of the coast. It pairs beautifully with a city or with Switzerland just over the border.

Sicily, for the Italy fewer people know

I lived in Sicily for seven months, and it left a mark. It is wilder, older, and more layered than the mainland: Greek temples, Baroque towns, Mount Etna, and food that draws from every civilization that ever landed there. Choose Sicily when you have done the highlights and want the version of Italy that surprises you.

Ready to go deeper? I have published full insider guides for Fora, a Virtuoso agency, on the Amalfi Coast, Tuscany, the Italian Lakes, Italy's wine regions, and Sicily, with the hotels and towns named.

Planning a milestone trip or bringing a group along? See how the levels of support work, or start with my Group Travel Planning Guide.

Start Planning Your Italy Trip

Photography via Wikimedia Commons: Positano (Italy) 04 by Bernard Gagnon (CC BY 4.0); Val D Orcia In Autumn (179351679) by Fabrizio Lunardi (CC0); Venice awakes (20618763815) by Benh LIEU SONG (Flickr) (CC BY-SA 4.0).