Like so many passionate travelers, Brooklyn-based couple Jen Lavino and Ryan Brown were itching to see the world while homebound during the pandemic. So once they got engaged in 2022, they started mulling a destination wedding; at first considering Montauk, where they vacation every summer, before realizing how high the pricing there would be. “Ryan’s really into golf, so I [alternatively] looked at golf courses in South Carolina and Georgia,” says Jen, who works for a Danish fashion brand.
But another place that she’s loved her whole life, pulled at her. “I always wanted to get married in Italy, but it felt out of reach,” the bride, whose father’s family originated in a town outside of Naples, explains. She’d grown up living with her Italian grandmother, and a previous job had brought her to Italy several times a year. Ryan, who works in sales and as a model, would often meet her there to explore more of the country, so Italy meant a lot to both of them.
Once the bride-to-be ventured into the research—venues, asking family and friends if they’d be willing and able to go—she was surprised to realize how reasonably priced it could be, and how excited people were to make the trip. Here, the couple share some of that research (and lessons learned) for those who are looking to wed in the land of la dolce vita.
Start with the venue type, not the region…
Although Jen has family ties to Naples, the couple weren’t exclusively focused on getting married there. Their first concern was finding a space that felt intimate: “What we both envisioned was a small enough place that our friends and family could stay with us for multiple days—something we could take over, just us,” says Jen. “We kept saying, ‘Let's go on vacation with our best friends and family,” agrees Ryan.
From there, they determined other priorities: Since Ryan grew up around farmland in southern Delaware, they were interested in marrying in a farm-like setting, but they also consider themselves “beach people,” and wanted to be near the water. Those qualities led them to consider Sicily and Puglia, and from there they zeroed in on their perfect property.
...and let that venue inspire the whole vibe.
They found their unicorn venue in Masseria Calderisi, a 17th-century working farm with 24 acres of olive, almond, and citrus trees just a few miles from the Adriatic Sea. The estate’s whitewashed, tufa-stone home had been transformed into a 24-room boutique hotel, where a complimentary shuttle ushered guests to the beach.
“I loved that they kept the aesthetic of the original masseria, so it didn’t look too ornate or anything—it’s really simple and beautiful,” Jen says of the minimalist look. “The whole vibe in Puglia is ‘slow living,’ and the masseria was very zen and peaceful.”
“You’d look outside your room to the gardens with oranges and pomegranates,” Ryan recalls. “It blows you away, takes away all your worries and stress.” They carried that atmosphere into many of their style choices, opting for the simple, vintage elegance of white flowers and fruit-topped tables.
Hop on a plane as soon as you can
After falling in love online with the masseria, Jen next flipped for the staff, who were instantly warm and accommodating in their email exchanges. Once she learned a date was available in the deeply desirable first half of September 2023—after July’s heat and August’s Ferragosto holidays that shut down the country—the bride took a leap. “She talked to them on a Friday, and was on a flight going there on Sunday,” Ryan laughs.
Her best friend, who was already in London for work, flew over to help her assess the venue. “They offered to give us a full tour on Zoom, and I said, ‘No, I know myself. I have to feel it,’” Jen says. But even with the high stakes, "it was hard to be stressed there,” Jen says. They booked for September 15 with 90 guests. One more planning trip to the area followed in April 2023, when the couple went together for menu tastings, and Jen’s trials with hair and makeup artists.
Rely on expert loved ones…
Another friend of Jen’s had married a Milanese man at a celebration in Sicily, and offered up her encyclopedic research of Italian wedding venues across the country. A third pal who is a wedding planner herself, Missy Ruiz, also stepped in to assist Jen. “She helped a lot with my inspiration; I was sending her pictures all the time, and she was on my Pinterest and built out this beautiful deck of the vibe,” Jen says.
And in a funny bit of serendipity, the bride’s mother discovered their wedding entertainment on a trip to southern Italy the summer of 2022. “They were there during a heat wave, and kept going to this one pizza place because it had air conditioning, where a guy was singing there every night, and was so fun that he had the whole place dancing,” Jen says. It turned out the man, Gerry Gennarelli, had a full eponymous band that plays events, and the couple happily booked them.
…and take a leap on a stranger’s local vendors
Even with all that assistance, the couple had to do plenty of their own research to find the right people that would fill in the details of their wedding. Since word of mouth was out of the question, the bride combed through Instagram, striking gold when she found another Brooklynite’s destination wedding in Puglia. Jen messaged the bride, who handed over her list of vendors. Though the pair had done so much of the planning themselves, they still opted to hire a local coordinator, Giusy D'Ambrosio, who assisted chiefly with communicating with these contractors in Italian. “It helped to have someone there, on the ground, facilitating some of these things,” says Jen. “I think she got us some good pricing, too, just because she's a local.”
Advise guests on the basics
The couple’s wedding website included a travel guide, packed with practical information for their 90 guests. The bride’s mother also happens to work at an airline, so had loads of expertise to offer as people made their bookings. Still, getting to Italy was complicated by the most essential item any traveler needs: “We had a lot of issues with guests not getting their passport renewals in time,” says Ryan. “A few family members waited over 20 weeks, [even] with expedited processing, to receive their passports, and still didn’t get them on time and so sadly had to miss [the wedding].”
While the U.S. State Department announced last fall that the 2022-2023 backlog was finally easing up, it can still take up to ten weeks for applications to be processed. Once a wedding date is set, it’s never too early to get rolling on a renewal.
The region-specific concerns
Once passports were in hand, the flights to the area were relatively simple; the couple found that most major European cities’ airports—such as London, Munich, and Paris—had connections to Puglia. It was a bit trickier to get from the airport to the Masseria, however.
“Most of our friends are so used to Uber, but our venue was in the middle of nowhere. It’s down basically a dirt road,” Ryan says. Their guests couldn’t quite grasp that a rental car was a necessity if they felt like leaving the property or extending their trips.
“That is one of the only downfalls of the region: There's really no public transportation, and it’s impossible to get taxis,” Jen says. “We provided transportation over the three days of the wedding, but if you were staying beyond those days or wanted to explore, it was really important that you rent a car.”
Watch out for that Italian pace of life
The couple married on Friday, September 15. A welcome barbecue was held on the beach on Thursday to welcome guests, and there was a pool party with pizza on Saturday to help them recover. It was in those final days that some cultural issues popped up, namely around a typical American wedding day’s rhythms and how long each part of the day should last, though Jen chalks these differences up to minor miscommunications. “You have to be on top of the timing, because I think that they cut it close. It's so relaxed there!” she explains.
The guests, too, didn’t pace their stomachs. “We had a buffet [during cocktail hour] and people thought that was the food. We were seeing people come back with full plates and we were like, ‘Wait, there’s a full meal after this!’” Ryan says. “It was a wild amount of food they served.”
In the end, though, “None of those details mattered. We just had so much fun. My friends still talk about it,” says Jen. The party wore on into the wee hours, with a DJ, Enzo Bonerba of Rinaldi Events, taking over after the band and playing until 3:30am. The couple had gotten their wish: “There was just an ease [like] when you’re on vacation,” the bride adds. “We could have stayed up all night dancing because there was just no stress.”
Originally Appeared on Condé Nast Traveler