Timing is everything in baseball. It’s also everything in love. But back in November 2017, Justin Verlander and Kate Upton found themselves in a scheduling nightmare that most couples would find impossible to navigate. Basically, they almost missed their own wedding because of a little thing called Game 7 of the World Series.
You’ve probably seen the glossy photos. The sun-drenched Tuscan hills, the Valentino lace, the wide-eyed joy. But behind those pictures was a week of pure, unadulterated chaos that ended with the Justin Verlander and Kate Upton wedding becoming one of the most legendary "double-ring" ceremonies in sports history.
The World Series Conflict Nobody Saw Coming
When the couple first planned their destination wedding at the Rosewood Castiglion del Bosco in Tuscany, Justin was still pitching for the Detroit Tigers. At the time, a deep November playoff run seemed unlikely. Then came the trade to the Houston Astros. Suddenly, Justin wasn't just in the playoffs; he was the ace leading a team to their first-ever title.
While their friends and family were already sipping Brunello di Montalcino in Italy, Justin and Kate were still in Los Angeles.
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Imagine being a guest at a wedding where the groom is literally on national television 6,000 miles away. That was the reality. On November 1, 2017, Verlander was at Dodger Stadium celebrating a World Series win. On November 4, he was supposed to be at the altar.
He had to skip the Houston championship parade. Think about that for a second. You win the biggest trophy in your profession, and instead of riding on a float through downtown Houston with a million screaming fans, you’re sprinting to a private jet. Honestly, it’s the only acceptable excuse for missing a parade.
Why Tuscany? The Rosewood Castiglion del Bosco
The choice of venue wasn't just about luxury, though the Rosewood is about as high-end as it gets. It’s a 5,000-acre estate with an 800-year history. They chose it because it was one of the first places they vacationed together. They wanted it to feel like a "vacation with their closest friends," which is a bit of an understatement when your guest list includes some of the world’s most famous faces.
The ceremony didn't happen in a ballroom.
It happened in a medieval church overlooking the Montalcino valley.
Thirty minutes. That’s all it took.
The aisle was lined with hurricane candles and olive branches. It was simple, but in that "it cost more than my house" kind of way.
The "Uplander Olympics"
Because they are a competitive couple, they didn't just have a rehearsal dinner. They hosted the "Uplander Olympics." We’re talking custom Under Armour jerseys for the guests, obstacle courses, and relay races. It’s kinda hilarious to think about supermodels and professional athletes getting sweaty and competitive in the Italian countryside just hours before putting on black tie attire.
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The Fashion: Two Dresses and a "Just Married" Secret
Kate Upton is a fashion icon, so the expectations for her gown were sky-high. She didn't disappoint. She collaborated with the team at Valentino for her ceremony dress. It featured:
- Intricate Chantilly lace.
- Sheer long sleeves that gave off serious Grace Kelly vibes.
- A massive, cathedral-length veil.
- Delicate floral embroidery.
But she didn't stay in that lace all night. For the reception, she swapped the tradition for something a bit more "late-night party." She moved into a draped, high-slit gown by Christy Rilling Studio.
Justin didn't just wear a standard tux, either. He went with Cicchini Custom Clothier. The cool part? He had "Just Married" embroidered inside the jacket. When he held it open during the party, it was the ultimate "we actually made it" moment.
The Red Party
The night before the wedding, they threw a "Red Party." The dress code was strictly red. Kate wore a stunning red lace Valentino gown, and Justin rocked a custom red tuxedo jacket. It was bold, visually striking, and probably looked incredible against the green Tuscan backdrop.
Misconceptions About the Big Day
People often think celebrity weddings are these cold, staged events. From everything reported by guests and the photographers (KT Merry handled the shots), this was the opposite.
One of the most human moments was the cake cutting. Kate surprised Justin with a massive firework show right as they sliced into the cake. After that? They didn't go to a quiet suite. They dragged everyone to a nearby villa for late-night karaoke.
Can you imagine being the person at the Rosewood hearing a World Series champion and a supermodel belt out karaoke at 2:00 AM?
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E-E-A-T: The Experts Behind the Event
This wasn't a DIY job. To pull off a wedding while the groom is in the World Series, you need a titan in the industry. They hired Lisa Vorce, a world-renowned celebrity wedding planner. Vorce is the same person who handled John Legend and Chrissy Teigen’s wedding.
The beauty team was equally prestigious. Hairstylist John Ruggiero and makeup artist Tracy Murphy (who are Kate’s actual friends) kept the look "effortlessly chic." This wasn't about heavy contouring; it was about looking like the best version of yourself after a 12-hour flight and a week of high-stress baseball.
Practical Insights for Planning Your Own (Less Chaotic) Event
Even if you don't have a private jet or a Valentino budget, there are things to learn from the Justin Verlander and Kate Upton wedding.
- Trust your vendors. If your schedule goes off the rails (hopefully not because of a Game 7), having a team like Lisa Vorce means the party goes on without you until you land.
- Theme your events. The "Red Party" and "Uplander Olympics" gave the weekend a cohesive feel that guests still talk about years later.
- Prioritize the "vacation" feel. By picking a venue where everyone stayed on-site, they turned a wedding into an experience.
The week Verlander had is statistically improbable. He won a World Series, missed his parade, flew across the Atlantic, and got married to a supermodel in Tuscany all within about 72 hours. It’s the kind of story that would be rejected by a movie studio for being too unrealistic.
If you're planning a destination wedding, your biggest takeaway should be the importance of a "plan B" and a very fast plane.
Next Steps for Your Wedding Planning:
- Research the legal requirements for a wedding in Italy (it's more complicated than you think).
- Look into the Rosewood Castiglion del Bosco as a potential venue if you have a high-tier budget.
- Consider a "transition dress" for your reception to ensure you can actually dance.