My love of Italy began with a tour when I was a student. I’ve been back more than 20 times as a travel professional, now in the ultra-luxury style that Italy affords those in the know, and I’ve planned countless trips for clients, with interests ranging from art and history to wine and pure indulgence. You could go to Italy every year for the rest of your life and have a different experience every time. 

For food and wine, my favorite region is Tuscany, where you are surrounded by vineyards, olive groves and farmlands so your food can be literally farm-to-table. Strolling in Florence, Italy’s center for Renaissance art, you can’t cross a bridge or walk down a street without seeing amazing sculptures and art. Even non-art enthusiasts will benefit from a personally guided tour of the Uffizi Gallery, which houses masterpieces by Raphael, Michelangelo and others. One of the fascinating bits of history is revealed by the Vasari Corridor connecting the Palazzo Vecchio (Old Palace) with the Palazzo Pitti (Small Palace). This covered walkway allowed the 16th century Duke Cosimo I de' Medici to move safely between his residence and his home, an illustration of the tumultuous politics of the era. 

For romance and scenic beauty, I often suggest the island of Capri, which is like the Martha’s Vineyard of Italy. Here, the charming Mediterranean style Capri Palace Hotel & Spa offers a private beach club, Michelin-starred dining and a holistic wellness spa. The 70-room hotel, built in the style of an 18th century Neapolitan palace, has an amazing art collection, and at your doorstep is the famous Blue Grotto and the timeless village of Anacapri, where you can shop for handmade sandals and other crafts. I also suggest chartering a private boat to motor around the craggy cliffs of the Gulf of Naples. Back on the mainland, Le Sirenuse makes a great home base for exploring Positano and the Amalfi Coast. In addition to a Michelin starred restaurant and sumptuous room with terraces overlooking Positano and the Bay, the hotel has a spa designed by the same architect who created the Musée d’Orsay in Paris. Nearby, you also visit postcard-perfect coastal towns like Amalfi and Ravello, Mt. Vesuvius National Park, and the well-preserved baths, theatres and villas of Herculaneum, buried in mud by Mt. Vesuvius in 79 AD. And there is so much more, from the Italian Lake District to the hiking and ski resorts of the Dolomites.

In addition to the museums and historic sites of Italy’s cities, there are lesser known sites that provide insights into the past. Many of my clients enjoy seeing the Jewish quarters in cities like Rome and Venice, and wine lovers often add a side trip from Venice to Slovenia. Everywhere, visitors receive a friendly welcome and are amazed at how this nation has managed to preserve not only its historic sites but its unique culture. Most clients I send to Italy want me to plan another trip to this amazing country—and another.