I Grew Up Hearing My Father's WWII Stories About Italy—Now I Plan Dream Trips There

Travel + Leisure

4 days ago

As the youngest child of a WWII veteran, I grew up hearing about the beauty of Italy, where my father spent the majority of his time in the army. While he never shared details of the battlefield, he would often tell me about the amazing places and people he met while stationed there.
I first visited Italy in my 30s, and it continues to call me back decades later; I now have a home in the mountains of northwest Tuscany, just north of Lucca, and have been in the luxury travel business for nearly four decades.
As a travel advisor, I help people plan their dream trips, and Italy is the top destination they wish to head to. When choosing where in the country to send them, Tuscany is an easy choice: It has historical cities and villages, beautiful land and seascapes, incredible food and wine, gracious residents, and unmatched art and culture.
Below, find an 11-night itinerary to Tuscany that showcases the very best of what this region has to offer. An aerial view of Santa Maria Del Fiore in Florence, Italy.
The trip begins in Florence, where guests can stay at Palazzo Portinari Salviati—the childhood home of Cosimo I de Medici, the former Grand Duke of Tuscany. The property has just 13 suites, each of which showcase a piece of history with decorated ceilings and marble accents. In the city, a former top Italian fashion model, Massimo Russo, who is now building his own fashion and home furnishing brand, will be your personal guide. This leg of the trip will conclude with a reservation at Enoteca Pinchiorri, a fine dining restaurant in the city's center. Elba Island, found on the Tuscan Coast.
After exploring the city of Florence, you'll escape to the coast. The chosen accommodation is Il Bottaccio, Relais & Châteaux, a restored 18th-century watermill with just eight exclusive rooms and suites. Here, expert guides will take you under their wing; learn how marble is extracted in some of the world's most famous quarries, which are then crafted into works of art.
To end the first week of the trip, you'll travel to Montaione, a small commune where the luxe Castelfalfi is located. This property is frequently named by readers to Travel + Leisure's World's Best Awards, and it's no surprise why: Set in the countryside, it boasts a spa, an indoor and outdoor heated pool, sprawling vineyards that produce organic wine, and a 27-hole golf course. A landscape of Gimignano, Tuscany, Italy.
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Day eight is an exploration of Volterra, a city known for its Alabaster (a finely carved mineral), followed by a wine tour at Badia di Morrona, an estate located in Terricciola in the wine region of Tuscany. This property, which centers around an 11th-century Benedictine abbey, produces wine like the famous Chianti DOCG.
From there, you will travel south to Castello di Vicarello, an ancient 12th-century castle turned award-winning accommodation. for a little reset. While it's set in an isolated medieval castle, the service has a modern touch. Plus, the on-site restaurant's terroir-based menu, centered on organic ingredients from local small producers, is a standout; guests can join in on family-run cooking classes, attend wine tastings in the vineyard, or go truffle hunting. Located midway between Rome and Florence, this five star retreat boasts a travertine infinity pool with vast panoramic views.
To complete the journey, I recommend staying at Il Borro, the estate of one of Italy's most fashionable families, the Ferragamo family. Here, Vittoria Ferragamo will personally welcome you and complete—what I hope—is one of the most remarkable and memorable travels of your life.
Keith Waldon is a member of Travel + Leisure's A-List and Travel Advisory Board. He specializes in Italy trips. You can create a tailor-made itinerary with Waldon by contacting him at [email protected] .