It was the summer of 2019 when it dawned on me, as I sat on the sweltering platform of the Long Island Railroad. “Why are we doing this?” I thought to myself, looking around at the hundreds of other red-faced weekend warriors. “Why are we trekking out to the Hamptons when Italy awaits us?” 

With summer 2020 chalked up to a total loss on the travel front, I came into 2021 with a clear goal — to make my Italian summer dreams true. In my mind, this meant a month or so of lazy seaside living plucked straight from The Talented Mr. Ripley, minus the bloodshed.  Alas with some scheduling constraints, my jaunt wound up comprising two weeks of non-stop action, road-tripping up “the boot,” starting in Sicily and ending in Florence. The goal? To maximize my time overseas, harnessing that pent-up passion for the finer things in life and making them a reality. 

Here, just a few of the highlights from my Italy Itinerary, if done properly, afford you a week of beautiful Italiano bliss in these off-the-beaten-path properties.  

Sicily — Rocca Delle Tre Contrade 

Image Credit Rocca delle Tre Contrade

I kicked off with my Italy jaunt with a stay at Rocca delle Tre Contrade with my friends Matt Hranek and Yolanda Edwards, founder of Yolo Journal, who handpicked this sprawling private home-turned-resort getaway after connecting via Instagram with its founder, Jon Moslet. Located 45 minutes from Catania airport, the 12-bedroom home offers a residential feel and easy access to nearby towns like Syracuse, Noto, and Taormina. Perhaps best of all though is the dining, led by an astute staff of locals who share their prized family recipes with guests. The breakfast granita, lunchtime Vitello Tonnato, and the beautifully simple zucchini and parmesan pasta at dinnertime are all must-haves, all enjoyed in the home’s backyard, with an unbeatable view of the often-active volcano, Mount Etna. 

Positano — Le Sirenuse 

Built right into the cliffside, Le Sirenuse in Positano is a true center of gravity where well-heeled visitors to the seaside town are known to congregate thanks to the property’s myriad dining areas and watering holes chock full of blue-chip artwork. A former private holiday home for the Sersale family, the hotel opened its doors in 1951 and remains a family-owned and operated business hosted by Carla and Antonio Sersale, along with their sons Francesco and Aldo, who are often found on-property welcoming guests with a selection of showstopping cocktails, including a yellow Bloody Mary made from local tomatoes. 

Conca Dei Marini — Monastero Santa Rosa 

Image Credit Monastero Santa Ros

Located about 30 minutes from Positano, Monastero Santa Rosa is a true self-contained retreat. Converted from a 17th-century monastery, the 20-room property offers several cheeky nods to the building’s religious past, including a confessional booth and a set of church bells that chime upon your arrival, along with an extensive spa and pool facility overlooking the Mediterranean. It’s Chef Christoph Bob who is the main attraction for many food-loving guests, thanks to his Michelin-starred dinner service that changes nightly based on the seasonality of local ingredients. 

Tuscany — Castello Di Vicarello 

With just nine rooms, a visit to Castello di Vicarello is akin to visiting a friend’s home for the weekend. Situated between Rome and Florence in the Tuscan countryside, the property is surrounded by rolling hills and endless rows of grapevines that produce the hotel’s selection of house wines. Much like Le Sirenuse, the Baccheschi-Berti family,  including their adorable Labrador Uva, can be found leading wine tastings and hunting excursions with guests. 

Florence — Belmond Villa Michele 

Image Credit Belmond Villa San Michele

Set just outside the center of Florence, the Belmond Villa San Michele is a slice of Italian aristocratic living, which is made immediately evident when greeted by the building’s facade, attributed to Michaelangelo. Inside, the 45-room property offers a secluded approach to city living, with most rooms offering a private garden or terrace overlooking downtown Florence. 

Discover More of Italy

There is so much culture, glamour, and romance on offer in Italy.  Lovers can immerse themselves in Tuscany’s stunning natural hot springs. Nature lovers will be equally enamored by the sapphire blue waters of famed celebrity hotspot Lake Como. Fusing alpine glamour with Mediterranean sexiness, the lake is surrounded by neoclassical villas including the 18th-century villa owned by George Clooney and his wife Amal. Then there’s the fairytale floating city of Venice, with its famous architecture (including St. Mark’s Basilica, a beach of Italo-Byzantine architecture), rich art history, and gondola-filled canals lined with Renaissance and Gothic palaces. Speaking of fairy tales, no trip to Italy is complete without visiting Florence.  ​​The famed Italian city stuns with terracotta-roofed buildings, majestic palazzi, swoon-worthy sculptures, perfectly manicured gardens, and of course the piece de resistance, the Duomo, capped by Brunelleschi’s astonishing red dome. 

For more from Zachary Weiss follow him on Instagram @zacharyweiss