A Journey From Milan to Sicily: Discovering Italy with Rocco Forte Hotels
Some trips remind me why I love what I do, and my recent journey through Italy with Rocco Forte Hotels was certainly one of them. From the fashion and energy of Milan to the history, incredible food, and beautiful landscapes of Sicily, every stop offered something different.
What I love most about traveling is discovering the experiences that make a destination memorable. Of course, I love a beautiful hotel, but it is often the unexpected moments, the people I meet, and the experiences I might never have discovered on my own that stay with me long after I return home. This trip gave me plenty of those moments, and I came home with some wonderful new recommendations to share with my clients.
Milan: A Little Shopping Never Hurts
Milan was our first stop, and what a fun way to start! I loved the city's mix of fashion, design, great restaurants, and historic neighborhoods. It has a sophisticated energy that feels distinctly Italian, yet different from other Italian cities I have visited.
We stayed at The Carlton Milan, which made a wonderful home base for exploring the city. I also had the opportunity to tour Rocco Forte House, which offers beautiful one-, two-, and three-bedroom apartments. I can see these being a great option for families or clients planning an extended stay who would appreciate extra space while still enjoying the comforts and service of a luxury hotel.
One of my favorite experiences was exploring Milan with Access Italy, followed by a personal shopping experience and an exclusive visit to Bianchi e Nardi. We learned about the history and craftsmanship behind luxury handbags, and I came away with a new appreciation for the artistry involved.
Here is the funny part: I have never really considered myself much of a shopper, but I couldn't resist purchasing a beautiful handbag. I ended up wearing it almost every night for the rest of the trip!
I guess sometimes the best purchases are the ones you never planned to make.
I would absolutely encourage anyone visiting Italy to spend a few days in Milan rather than treating it as simply a stopover. Between the shopping, art, restaurants, and neighborhoods, there is plenty to enjoy.
Florence: A Taste of Tuscany and a Very Special Rooftop Aperitivo
From Milan, our group took the high-speed train to Florence, which was an easy and enjoyable way to travel between the two cities. We stayed at Hotel Savoy, right in the heart of Florence and perfectly positioned for exploring on foot.
One of my favorite outings was a private visit to Castello del Trebbio, where we toured the property and enjoyed tastings of olive oil, balsamic vinegar, and wine. I loved getting outside the city and experiencing a different side of Tuscany. It was a wonderful opportunity to learn about local products, enjoy the countryside, and slow down for a bit after exploring the city.
Another highlight was an aperitivo at Palazzo Gondi, arranged by Access Italy. Designed in 1489 by Giuliano da Sangallo, a favored architect of Lorenzo de' Medici, the historic palace remains in the Gondi family today.
We had the opportunity to tour the palace and enjoy cocktails on the rooftop with family members Gerardo and Lapo. I found it fascinating to hear about the family's history while standing in a place that has been part of Florence for centuries.
There is something special about experiencing a historic home with the people whose family stories are part of its history. I could have visited another beautiful landmark, but meeting members of the Gondi family and hearing their stories made this experience feel much more personal.
That is one of the things I appreciate most about private touring. I don't just want to see a place; I want to understand its story and come away with a better feel for the people and culture behind it.
Sicily: History, an Unforgettable Lunch, and Time to Unwind
After a short flight from Florence, we arrived in Palermo, where we stayed at Villa Igiea. Overlooking the water, this beautiful historic property has a sense of old-world grandeur that feels distinctly Sicilian. I loved having the opportunity to experience the hotel itself rather than simply using it as a place to sleep between excursions.
One of the most memorable days of our trip was our excursion to the Valley of the Temples. Essence of Sicily arranged a private experience that included lunch in their own secret garden overlooking the ancient Greek temples. The setting was breathtaking, and the farm-to-table meal was just as special. It was one of those experiences that is difficult to put into words and that I know I will remember for years to come.
After our day exploring this remarkable part of Sicily, we continued to Verdura Resort on the island's southern coast. The change of pace was wonderful. We stayed in a villa with plenty of room to spread out and relax poolside, which was exactly what I needed after several busy days of exploring cities and historic sites.
Dinner at the resort's Osteria was another highlight. I was served sea bass prepared tableside in a salt crust, making an already wonderful meal feel like an experience in itself.
I loved how these two parts of Sicily complemented each other: a day immersed in ancient history, followed by time to relax at a beautiful coastal resort. For me, that balance is what makes a trip truly special. I want to explore and learn about a destination, but I also want time to enjoy where I am without feeling as though I need to be on the go every minute.
If you have already visited Rome, Florence, or the Amalfi Coast and are looking for a different side of Italy, I would absolutely consider Sicily. I came away feeling that there is so much more to discover here, and I would happily return.
What I Brought Home from This Trip
One of the biggest things this trip reinforced for me is that I don't believe the best itinerary is necessarily the one that fits in the most stops. I think it is about finding the right combination of places, experiences, and time to enjoy them.
I loved the energy and shopping in Milan, the history and countryside experiences around Florence, and the combination of culture, incredible food, and relaxation in Sicily. Each destination felt different, and together they made for a wonderful Italian journey.
I also came away with a better understanding of how the Rocco Forte collection can work for different types of travelers. I can see the appeal of a stylish city hotel for a couple's getaway, the extra space of a private apartment for a family, or the privacy and relaxed pace of a villa at a resort.
Not every traveler wants the same thing, and that is part of the fun of planning. Some of my clients want to be out exploring from morning until evening. Others want a beautiful hotel, a few exceptional experiences, and plenty of time to relax. Most want a little of both.
As a travel advisor, I value opportunities like this because I get to experience the hotels firsthand, meet the people who bring these experiences to life, and discover the details that help me make thoughtful recommendations. When I suggest a hotel or a private experience to a client, I want to share more than a place to stay but offer an experience.
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