Real Couples on Planning a Wedding in Italy

A Roundtable Conversation with Michelle Durpetti Events

There is a particular kind of magic that happens when you bring real couples back to the table after their destination weddings in Italy. The logistics have settled, the emotions have softened into memory, and what remains is perspective: what truly mattered, what surprised them, and what they would tell anyone planning a wedding in Italy now.

In our first-ever Wedding Download roundtable at Gene & Georgetti in Chicago, Michelle sat down with two of our Italy destination wedding couples to talk about their multi-day celebrations—one in Sicily, one in Tuscany. Over aperitivo-style conversation, they shared everything from Netflix-meet-cute beginnings and family firsts abroad, to guest experience, regional food, and the very real impact of photo, video, and content creation.

This post is your companion to that conversation. You’ll find the full video embedded below, along with the key themes, lessons, and heartfelt moments that will resonate if you’re considering planning a wedding in Italy!

Press play on the roundtable below, then read on for the stories and takeaways our couples wish every Italy-bound pair knew.

Inside Our First Italy Wedding Roundtable

Two Love Stories, One Country

At the table were two very different couples with one beautiful throughline: a deep love for Italy and a desire to share that love with their favorite people.

One couple, originally from New Orleans, met in the most modern way possible—a Netflix dating show—and eventually chose Sicily as the place to gather their families, many of whom had never left the United States before. For them, the wedding week was as much about bringing parents “home” to their Sicilian roots as it was about their own vows.

Our second couple chose the Tuscan countryside, imagining one long table under chandeliers, surrounded by vineyards and friends from across the globe. Their vision was intensely specific—a single, cinematic tableau that lived in their minds for months. On the wedding night, as they looked down the table at sixty of their closest friends and family, they could literally see their vision translated into reality.

Different regions, different aesthetics—same country, same sense of wonder.

How Serendipity Shapes Planning a Wedding in Italy

Interestingly, neither couple’s journey was linear. One originally tried to work with a local planner in Sicily before that plan fell through. A single email and a “year of yes” later, we were connected—and what felt like a setback became the pivot that led them to a planner who could bridge American expectations with Italian culture.

That’s something Michelle talks about often: “I live with one foot in Italy and one foot in the U.S. I understand the urgency and communication style that American couples are accustomed to, but I also speak the language—literally and culturally—of Italian venues, caterers, and creative partners.”

When you’re planning a wedding in Italy, especially from abroad, this dual fluency matters. Our couples felt it in real time: from how quickly we could move decisions forward, to how we advocated for them with Italian vendors who operate on a very different rhythm.

Real Advice for Planning a Wedding in Italy

Our roundtable wasn’t about perfectly polished answers; it was about honest reflection. When Michelle asked each couple what they would tell anyone planning a wedding in Italy (beyond “hire a planner”), these themes came up again and again.

Take Your Time (And Then Add More)

Both couples said it almost in unison: take your time.

Planning a wedding in Italy happens across time zones, languages, and cultures. Email responses are slower. Decisions are more layered. August holidays happen. Life happens. The more lead time you have, the more gracefully you can navigate it all.

One couple planned their Sicily celebration in roughly six months—doable, but undeniably intense. Their advice for other couples was clear: if you have the luxury of a longer runway, take it. Give yourselves space to be thoughtful with design, guest logistics, and travel plans rather than feeling like everything is urgent all at once.

Time also matters during the wedding itself. Stretch your celebration into a weekend—or better yet, several days. Both couples hosted multi-day experiences: intimate rehearsal dinners, rooftop cocktails, winery lunches, and poolside moments that allowed everyone to arrive, settle in, and savor.

Because when guests are investing five figures to attend your celebration abroad, more than one night together feels not only generous, but essential.

Embracing the Italian Pace (Without Losing Yourself)

One of the most illuminating parts of the conversation was when our New Orleans couple talked about the Italian concept of time.

As they put it: “Italians don’t live to work. They work when they want to.”

Emails are answered eventually. Decisions are made after vacations. Responses that might take an hour in the U.S. could easily take days—or weeks—in Italy.

If you’re planning a wedding in Italy, this is not a flaw in the system. It’s the system.

The advice?

• Expect slower response times.
• Don’t panic when a vendor falls silent for a week.
• Let your planner handle the follow-ups and pressure.

Your job is to embrace the cultural difference rather than fight it. Our job is to translate your priorities into a cadence that works for local teams, while keeping your timeline on track.

Guest Experience as the True Luxury

One of the most moving threads in the roundtable was how much each couple centered their guests.

Parents who had never left the country. Siblings extending solo travel for the first time. A maid of honor navigating lost luggage and still falling in love with Italian beaches, markets, and wine bars.

For our Sicily couple, flying their families to the “motherland” became as meaningful as the ceremony itself. For our Tuscany couple, seating charts were crafted so that every guest had a “comfort person” next to them—no one left to make small talk with strangers all night.

A few guest-experience insights that emerged:

• Think of the wedding as an investment for your guests, too.
  They are spending money, time, and energy to be there. Give them a beautiful return on that investment.
• Design your days around how you want them to feel, not just how everything will look.
  That might mean shorter dinners and earlier dancing for an American-heavy guest list, even when Italian caterers are shocked you don’t want a five-hour, twelve-course progression.
• Create opportunities for your guests to fall in love with Italy for themselves.
  Winery lunches with pairings, free afternoons in hill towns, coastal boat days, late-night gelato walks—these are the memories they’ll talk about long after the flowers are gone.

In a true luxury destination wedding, the most elevated detail is often how cared for your guests feel.

Food, Wine & the Beauty of Regionality

As someone who grew up in a restaurant family, Michelle could talk about wedding food in Italy for hours—and in this roundtable, that’s what they essentially did.

What both couples discovered is that Italian cuisine is profoundly regional. There is no generic “Italian menu.” A wedding dinner on the slopes of Mount Etna will never look—or taste—like a menu in the Florentine countryside, and that’s the point.

Our couples leaned into that:

• In Sicily, lunches and dinners highlighted produce grown in volcanic soil: tomatoes, beans, potatoes, and herbs that tasted almost impossibly vivid.
• In Tuscany, the menu reflected local traditions and ingredients, paired with wines from neighboring vineyards and served at a long, candlelit table beneath the chandeliers the bride had dreamed of.

The result? Guests who actually talked about the food. Asked for seconds. Remembered individual dishes months later.

When you’re planning a wedding in Italy, this is where a planner with restaurant and hospitality experience can be invaluable—not just in curating menus, but in managing service pacing so that you still get to the dance floor at an hour your guests will love.

Why Photo, Video & Content Creation Matter Even More Abroad

One of the most practical lessons that came up was the impact of investing in both cinematographic video and real-time content creation.

Every couple at the table agreed:

• The wedding day is emotionally overwhelming.
• You will not remember everything.
• Video brings you back to the feeling in a way nothing else can.

A year after their weddings, our couples watched their films on their anniversaries and were transported—back to a flight of steps in Sicily, to a single long table in Tuscany, to their parents laughing over local wine.

We also talked about the complement between professional film and social-first content creation:

• Cinematic video captures the narrative, the atmosphere, the “movie of your life.”
• Content creation captures the in-between: behind-the-scenes clips, guest reactions, quiet moments of nerves and joy you might never see otherwise.

For destination weddings, where so much thought and investment goes into travel, attire, and design, having those layers of visual storytelling becomes an archive—not just for you, but for future children, families, and even your vendors (yes, we cherish those moments too).

Is Planning a Wedding in Italy Right for You?

As we wrapped our roundtable, I asked each couple for three pieces of advice they’d offer anyone considering planning a wedding in Italy. Their answers, distilled:

• Take your time.
  If you have the luxury of a longer planning timeline, use it—especially across borders.
• Hire a planner you truly trust and vibe with.
  You’re not just hiring logistics; you’re hiring advocacy, cultural translation, and creative partnership.
• Savor every minute.
  The process, the week, and especially the night itself pass quickly. Build in space to feel it, not just execute it.

If you’re dreaming of planning a wedding in Italy—not just for the photographs, but for the way it will shape your families, your friendships, and your memories—this conversation is for you.

Watch the full roundtable, listen to the laughter and emotion in our couples’ voices, and then decide if you’re ready to begin your own Italian chapter.

Because when it’s done with intention, cultural fluency, and genuine care, a wedding in Italy becomes more than a destination. It becomes part of your family’s story.

If you’re feeling called to Italy, but the logistics feel overwhelming, reach out. We’re here to make the journey as thoughtful as the destination.