An Italian-Inspired Rehearsal Dinner at a Private Estate in Milwaukee, Wisconsin

Picture this: The sun is setting over the Mediterranean Sea while you enjoy a dinner with close friends. You’re mid-laugh with an Aperol spritz in han

Picture this: The sun is setting over the Mediterranean Sea while you enjoy a dinner with close friends. You’re mid-laugh with an Aperol spritz in hand. A salty sea breeze wisps through the vegetation on the ocean-side cliffs. Sounds immensely relaxing, right? That laid-back vibe is exactly what Caroline Marks (26, an account executive) and Robert Flaherty (27, a real estate developer) wanted to bring to their rehearsal dinner in Milwaukee on August 18, 2023.

But before celebrating their Italian-themed meal in Wisconsin, the couple had to revisit a few other locales: spots where they dated and fell in love. Caroline and Robert met in college in Indiana and first bonded while watching a movie and eating takeout in Caroline’s dorm room. Upon graduation, they moved to Chicago. Despite dating in college, their love wasn’t truly sealed until a fateful trip to Naples, Florida, during the pandemic. The couple lived together for the first time when they decamped to the South for a few months to work remotely in the sun. “We both knew a week into living together that we were going to be together forever. It truly was too easy, fun and perfect,” says Caroline. That effortless love continued to blossom and culminated with a rooftop proposal at sunset in New York City. And the next day, where did the couple jet off to? You guessed it: Italy.

The tricky thing with a rehearsal dinner is this: How do you avoid competing with the main event that’s just around the corner? Caroline and Robert settled on an Italian-villa vibe that would feel different from their wedding day and nod back to a trip that had meant so much to them. The couple invited 62 guests to Caroline’s mother and stepfather’s home for a cozy dinner before a larger 130-person welcome party that same evening.

While the wedding day was designed to have a whimsical garden-party aesthetic with a light and airy color palette, Caroline and Robert selected richer hues for the rehearsal dinner. Vibrant textured greenery suspended from the ceiling of the clear-top tent, dark wood farm tables and deep blue water goblets anchored the event’s look and captivated guests. Instead of traditional floral centerpieces, the long wood tables were adorned with potted rosemary topiaries that mirrored the hanging foliage. The aim was to enjoy the fresh air but still be protected from the elements, and Caroline recalls that “the tent was truly stunning, and every detail was perfect.”

Not only was the visual design impeccable, but the menu was sublime. The signature drinks were, appropriately, two Italian classics: an Aperol spritz and a Negroni. Guests also enjoyed a four-course meal that began with a chopped salad before a primi course of Italian classics: rigatoni with tomato vodka sauce and cacio e pepe. The secondi course wowed with a selection of three grilled entrees: beef tenderloin, branzino and seasonal veggies. Once all the guests arrived for the welcome party portion of the evening, a dessert station opened serving ricotta cheesecake and Nutella cannoli; roaming waiters offered affogato and gelato.

It was important for Caroline and Robert to curate a team of talented wedding pros to bring the entire weekend together. Caroline urges other couples, “Hire vendors that you feel comfortable with. You will know after the first call if they’re a good fit or not.” Another key piece of advice she has for to-be-weds? “Remember to have fun and don’t stress about the little things. At the end of the day, you are marrying your person and that is all that matters.” 

Bride and Groom in Rehearsal Dinner Attire
Rehearsal Dinner at a Private Estate in Milwaukee, Wisconsin
Rehearsal Dinner Welcome Sign With Tile-Inspired Details
Caroline and her late grandmother shared a love of butterflies. To honor the matriarch, Caroline and Robert released freshly hatched mon- archs at the rehearsal dinner.
Clear Top Tent at a Private Estate in Milwaukee, Wisconsin
Custom illustrations added thoughtful personalization to the evening. The bar menu included mouthwatering drawings of the signature cocktails. Additionally, the welcome sign featured a design that resembled Italian tiles.
Aperol Spritz Cocktail for Rehearsal Dinner
Farm Table and Hanging Greenery at a Private Estate in Milwaukee, Wisconsin
Wood Farm Table With Blue Runner and Rosemary Topiary Centerpiece
The event’s clear-top tent ensured guests could enjoy the twinkling stars as the sun set. Additionally, string lights speckled the tent’s roof to add to the magical ambiance as the evening progressed.
Salad for Rehearsal Dinner at a Private Estate in Milwaukee, Wisconsin
Passed Hors d'Oeuvres for Rehearsal Dinner
Passed Appetizers at Rehearsal Dinner
Bride and Groom at Rehearsal Dinner at a Private Estate in Milwaukee, Wisconsin