It began with a wedding in Taormina, but for Inspirato member Joe, the real story was everything that came after. What started as a family celebration turned into something far more rare: a multi-generational reunion across Sicily, reconnecting cousins from around the world in the land their family once called home.
“My daughter was getting married in Sicily where we are from and we planned the wedding in Taormina,” Joe shared. “Because we were going to be in Sicily already, and knowing I have cousins in Palermo that I had not seen in 30 years, I thought it would be a great opportunity to plan a cousins’ Sicily trip.”
The idea quickly took hold. “When I mentioned it to everyone, they got really excited. When would all of us ever be together like this again? They told me if I planned it, they would all be in.”
“When I mentioned it to everyone, they got really excited. When would all of us ever be together like this again? They told me if I planned it, they would all be in.”
Joe had the vision. The Inspirato Bespoke team made it happen.
Turning a Dream into a Custom Journey
Joe had a clear goal. He wanted to bring his family together and experience all of Sicily, not just one part. That meant building a two-week itinerary that could accommodate eleven travelers, move efficiently across the island, and still feel relaxed and luxurious.
“I knew if I was going to make this happen, it would need to be done by [Inspirato],” he said. “[I was] introduced… to Asha and Julia, my Bespoke team, and the journey started.”
Joe described the planning process as collaborative, thoughtful, and above all, personal.
“I have to say they were both incredible. I wanted too many things but didn’t know how to put it all together in a two-week trip. Most trips only do either an eastern trip or a western trip of the island. I wanted to do both.”
They were kind, professional, and comfortable to deal with, which made it fun. I felt they became vested in the success of the cousins’ trip and part of the experience.”
What stood out to Joe was the team’s response to the complexity. “I gave them so much to deal with, but they didn’t tell me it wasn’t going to work. They told me we will figure something out to make this happen.”
Over several months, Asha and Julia worked closely with Joe to fine-tune every detail. “We went back and forth tons of times and never once did I get a sense that they were frustrated or upset. I felt they wanted to make this happen for me.”
More than planners, the Bespoke team became partners in the experience. “They were kind, professional, and comfortable to deal with, which made it fun. I felt they became vested in the success of the cousins’ trip and part of the experience.”
Highlights from the Itinerary: Sicily in Full Color
The final itinerary blended family heritage, culture, food, and relaxation. It began with a private transfer from Taormina, stopping in the hilltop village of Savoca, before arriving in the quiet coastal town of Sant’Agata di Militello. From there, the family journeyed westward across Sicily, with overnight stays in Cefalù, Ragusa, Agrigento, and Cinisi, experiencing both celebrated landmarks and hidden gems curated by the Inspirato Bespoke team.
One of Joe’s favorite experiences was in Savoca, a hilltop town famous for scenes from The Godfather. “There were so many memorable experiences, from seeing where The Godfather was made to seeing the ruins in Agrigento to experiencing the many small towns like Cefalù.”
It wasn’t just the destinations that made an impact. It was the people.
“What stands out the most throughout our trip was the people that Bespoke teamed us up with in Sicily,” he said. “We had so much fun with our transport drivers who became part of the family, to the excellent tour guides that made everything come to life, but most importantly were fun and excited to be part of the experience that day with a bunch of old Sicilians.”
A standout moment was the day spent at a working herb farm, where the owner and his wife welcomed the group into their greenhouse for a home-cooked lunch.
“One of our favorite tours was the herb farm with the owner and his wife cooking us a home-cooked meal in their greenhouse. It was one of our favorites.”
Tastes of Sicily: A Culinary Reunion
For a family with deep Sicilian roots, every meal carried emotional weight. “Being Sicilian, all the food was great,” Joe said, “but eating childhood foods like caponata, fresh fish, and homemade pastas brought back so many memories.”
The group enjoyed grilled octopus, local arancini, and bottles of organic Sicilian wine. But one treat rose above the rest.
“Everyone has gelato, but granita is an unbelievable tasting icing slushy with many natural flavors. The best is coffee flavor, and you eat it with a brioche. Best place to have one is at the BAM Bar in Taormina.”
Joe’s Tips for Members Planning Bespoke Travel
Now that he’s returned home with a heart full of memories, Joe has advice for other Inspirato members thinking about a Bespoke trip. “Let the Bespoke team help you with suggestions on places, restaurants, and tours. I knew what I was looking for, but their suggestions helped a lot.”
He also encourages members to avoid overpacking their itinerary and to enjoy longer stays in each destination or plan multiple trips when covering a lot of ground. “Try not to do everything on one trip like we did. We found some great places to be at and wished we had stayed longer in certain places.”
And above all, he recommends setting aside time in one special place. “Whatever you do, spend a few days in Taormina. It will be your favorite place in Sicily, trust me.”
A Journey That Will Be Remembered for a Lifetime
For Joe, this trip was about more than sightseeing. It was a chance to come together, to connect with family and culture, and to experience the joy of sharing it all in a way that felt effortless. “Besides my daughter getting married in Sicily and making my dream come true, it was family being together in places where our parents and grandparents were born and lived.”
For Joe, Inspirato didn’t just plan a vacation. They helped design a bespoke luxury vacation in Sicily that allowed the family to travel with ease while experiencing deep personal connection. “We made new memories that we would cherish for a lifetime.”
For anyone planning a custom Italy trip, Joe recommends leaning on the Bespoke team for guidance.
“We made new memories that we would cherish for a lifetime.”
Let Inspirato Bespoke Help You Plan Your Next Great Journey
Whether you are exploring your roots, gathering extended family, or dreaming of something completely your own, the Inspirato Bespoke team can turn ideas into extraordinary experiences.
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