I’ve always believed that life milestones deserve to be celebrated in style, and nothing says style like an Italian getaway.
So, when my friend decided to ring in his 40th birthday by recreating scenes from ‘Under the Tuscan Sun’, well, he had me at Ciao!
Five of us packed our bags and headed to the rolling hills of Cortona in Tuscany where the movie was filmed.
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Now, Chris is obsessed with ‘Under the Tuscan Sun’ for many reasons; Diane Lane’s character’s story of heartbreak, self-discovery, and gorgeous Italian scenery really struck a chord.
But for him it’s also considered an iconic gay film as even though it was released in 2003 it was one of the first movies he remembers with openly gay characters and storylines. Representation matters and should be celebrated.
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We were all thrilled that Cortona was our picturesque backdrop for a week of adventure, indulgence, and a little bit of Hollywood magic.
We stayed in a stunning Airbnb villa that might as well have been ripped straight from the screen. Complete with stone walls, terracotta roofs, and views that stretched across olive groves and vineyards, it was the kind of place that made you instantly relax.
Within minutes of arrival, we were lounging by the pool with a bottle of wine, toasting to Chris’ fabulous festival of 40.
The next day was all about exploring Cortona. It felt like we had stepped straight into a postcard. The town itself is perched on a hill, with narrow cobblestone streets winding through centuries-old buildings.
Did I mention it was steep? Calf muscles burning, it was important to take regular breaks, for drinks and snacks. But that’s perfect because it’s exactly the kind of place where you feel like time has slowed down.
It’s one of those towns that feels both intimate and grand all at once. Despite being small, every corner is packed with history and beauty. Ideal for soaking in the Italian lifestyle, with all the la dolce vita energy you could ever want.
Chris had meticulously mapped out all the iconic locations from the film. So, we hiked past the Villa Bramasole, the real-life home that inspired the movie, and then we took about 300 selfies with it. Apparently, you can rent the actual villa from the movie but it’s about 30 000 Euros a week – a tad out of our budget.
It turns out Cortona isn’t just about movie moments though, there’s real magic in its atmosphere. The people are warm and friendly, the food is out of this world, and the sunsets are so spectacular they should come with their own soundtrack.
Now, no trip to Tuscany would be complete without an obscene amount of food and wine, and we did not hold back. Every meal was an event, from hearty pasta dishes to fresh cheeses and, of course, endless antipasti platters.
Every bite was better than the last, and we paired everything with wines that were smooth, rich, and straight from local vineyards. Our favourite was a red from the Bramasole vineyard featured in the film.
For the birthday night itself, we went all out. A private chef prepared a dinner party in our villa, with the most spectacular sunset we’ve ever seen and the soft sounds of Italian music filling the air. Then we trekked up into town as we heard there was a dance festival on.
We were buzzed from wine and ready to dance the night away only to discover it was local kids doing demonstration of traditional folk dancing. A hilarious mistake that added to the joy of the night.
As we toasted to Chris, it was clear that this trip had become exactly what he wanted – a celebration of life, love, and friendship, with a touch of cinematic flair.
Leaving Cortona was bittersweet. It’s the kind of place that makes you feel like you’ve found a second home, even if you’ve only been there a week.
While we didn’t exactly buy a crumbling villa like Diane Lane’s character did, Chris got his Under the Tuscan Sun moment, we got a much-needed escape, and together we created memories that will last a lifetime.
I don’t know if life in Tuscany really is like the movies, but for one week, it felt like we were all stars in our own beautiful, sun-soaked film.
Shelly travelled at her own expense.
