Alex and Jack’s wedding in Taormina came with aperitivo in the garden, Sicilian food stations, plenty of limoncello, and views stretching from Isola Bella to Mount Etna. Later, dinner gave way to something much less formal: hours of karaoke, with guests choosing their own songs and passing the microphone around well into the night.

That mix was exactly what the couple had in mind for their Villa Mon Repos wedding. With friends and family traveling from the United States, they wanted to give everyone a reason to enjoy being in Sicily together rather than plan a wedding they could have just as easily had back home.

What We Love About This Villa Mon Repos Wedding

• A ceremony on a platform built over the villa’s pool
• Aperitivo with Sicilian food stations, limoncello, and a saxophone player
• Custom “The Elvington Club” hats waiting at every dinner seat
• Karaoke continuing for hours once the first guest picked up the microphone

Why Alex and Jack Changed Their Wedding Plans From Charleston to Sicily

Alex and Jack met seven years ago through mutual friends who were dating at the time. They grew up in the same hometown but had never crossed paths before that introduction. A few months later, they started dating and have been together ever since.

When wedding planning began, Italy wasn’t a part of the picture. “We were originally planning a wedding back home, in Charleston, South Carolina. After a few months, we realized we wanted something different and that is when we started looking abroad.”

They initially searched around Lake Como. Then Alex’s mom and sister, who had visited Taormina a few summers earlier, suggested looking at Sicily. The couple found Villa Mon Repos, with the sea and Isola Bella on one side and Taormina and Mount Etna on the other. The town was another selling point. Guests could explore on foot, and Alex and Jack could easily meet up with everyone in the days before the wedding rather than only seeing them at scheduled events.

Planning First Looks With More Than Just Each Other

Alex didn’t stop at a first look with Jack. She also planned them with her parents, Jack’s parents, her bridesmaids, and Jack’s three brothers. Part of the reason was practical. Getting those photos done beforehand meant she could spend more time with everyone after the ceremony rather than leaving for portraits. “Being able to see my favorite people before really calmed my nerves and I will never forget their reactions.”

Jayne, their planner, officiated the ceremony, keeping it lighthearted and quick at the couple’s request. Alex and Jack stood on a platform over the pool, with their guests gathered around them.

Once they were married, everyone stayed together for a champagne toast before heading into the garden for aperitivo. There were several stations serving Sicilian food, lots of limoncello, and a saxophone player while guests ate and caught up before dinner.

Traveling With the Wedding Dress Became Its Own Project

Finding a wedding dress took Alex a while. Then she realized she had to get it across the Atlantic. “This was probably the hardest task for me, I tried on so many dresses. I never thought about having to travel with the actual dress but I knew I wanted it to be big and something I had never seen before.” Her seamstress managed to pack the gown into a carry-on suitcase. Alex remembers worrying that the case looked ready to burst, but checking the dress and risking it getting lost wasn’t an option.

She and Jack traveled to Italy a few days early with their families. Jack went to Rome while Alex headed directly to Taormina, where she could finally unpack the gown. She and her parents then took turns steaming it every day. Getting it to the villa created one more problem because there was no way it was going back into the suitcase. Luckily, a friend had a rental car and drove the unpacked dress to Villa Mon Repos on the wedding morning. “It was definitely an adventure with the dress!”

Featured Vendor:
FBalzan Photography

Taking Their Time to Find Vendors They Actually Clicked With

Working with people they actually got along with mattered to Alex and Jack, so they didn’t book the first available options. “We wanted vendors that matched our style, fun and easy going. We met with several different vendors before finding the right ones.” Planner Jayne Seddon of Casa Collina Events was one of their first bookings. She listened to their ideas, helped them plan from abroad, and eventually served as their officiant as well.

Photography was booked early too. Alex and Jack wanted images that captured what was happening without turning the day into a long series of posed shots, which led them to Junebug vendor Franklin Balzan. For flowers, Alex found Petali e Capricci Weddings on Instagram and liked that local flowers could be used without overwhelming the property.

Food, music, and photography received the largest share of their attention and budget. Catering came directly through Villa Mon Repos, which also handled the alcohol, tables, and chairs. Blue Sound 2 covered the music and, importantly, was happy to make room for the DJ and karaoke Alex and Jack already knew would be part of the night.

Keeping the Decor Simple With Views in Every Direction

Flower arrangements were placed around the property along with a few traditional Sicilian ceramic head planters, but Alex and Jack otherwise kept things fairly restrained. The dress code brought in more color. The wedding was black tie, with tuxedos for the men and floor-length dresses in fun Italian summer colors for the women. 

Alex used a similar approach with her bridesmaids. Each was assigned a color and given a few guidelines, but they chose their own dresses. “I wanted them to feel like themselves in whatever style of dress they chose rather than having them all in the same exact thing.” Jack and his groomsmen wore white dinner jackets with bow ties.

Personalized Hats Quickly Took Over the Reception

One of the couple’s few personalized details was waiting on the dinner chairs. Each guest received an “The Elvington Club” hat, along with Taormina and 2026. They were supposed to be favors, but almost immediately became part of the party.

“Everyone was putting them on and taking pictures. As we entered, some were swinging them around.” Many guests kept them on for the rest of the night, so the hats ended up appearing in plenty of the reception photos too.

Karaoke Was Always Going to Be Part of This Reception

Karaoke wasn’t a spontaneous reception addition. Alex and Jack love to sing, their friends love to sing, and they knew from the start that they wanted it at the wedding. Once the band finished and the karaoke began, there wasn’t much hesitation. “We love to sing and so do our guests, so it took no time for the first person to grab the microphone and it never ended after that.”

There was no fixed song list. Guests chose whatever they wanted, and the microphone continued making its way around the room for hours. It’s still one of the parts of the wedding Alex and Jack talk about most with their friends.

Why the Days Before the Wedding Mattered Just as Much

Because so many guests had traveled internationally, Alex and Jack gave everyone opportunities to spend time together before the ceremony too. After a quick rehearsal, they hosted a welcome party at Villa Zuccaro, a restaurant Jayne had visited herself while in Taormina a few months earlier. It gave everyone a place to gather before the wedding while still leaving plenty of time to explore the town on their own.

For Alex and Jack, that extra time together is also why they’d recommend a destination wedding to anyone already considering one. “If anyone is thinking about having a destination wedding, do it! It created the most unforgettable memories and there is something so special about having so many people travel to another country just to celebrate your marriage.”

Their wedding may have started out as plans for Charleston, but Taormina gave them something they couldn’t recreate there: several days in one walkable town with the people who had traveled across the world to be with them, capped off by dinner, limoncello, personalized hats, and a microphone that apparently nobody wanted to put down.