Castello del Trebbio Wedding: Alyssa & Ryan’s Three Days in Tuscany

Alyssa and Ryan got married at Castello del Trebbio in July, with 60-something guests and three days in the hills above Florence: a welcome dinner, the wedding day and a karaoke night to close. I was there for all three, shooting on digital and on film.

What I remember most is how much they laughed. Not the polite laugh you get when someone points a camera at you, the real one. Their friends were exactly the same. If you’re looking for a quiet, formal Tuscan wedding, this isn’t it, and I mean that as a compliment.

Quick facts

  • Photographer: Federico Pannacci (Fedepan), wedding photographer based in Siena, Tuscany
  • Couple: Alyssa & Ryan
  • Venue: Castello del Trebbio, Santa Brigida (Pontassieve), near Florence
  • Date: 25 July 2026
  • Guests: 60 to 70
  • Coverage: three days, welcome dinner, wedding day and karaoke night
  • Planner: Tuscania Wedding Events
  • Shot on: digital and film

Castello del Trebbio, half an hour from Florence

The castle is in Santa Brigida, near Pontassieve, in the Chianti Rufina hills. Parts of it go back to the 1100s, and today the family that owns it runs an organic winery there. Vineyards, olive trees and cypresses all around.

I like working here because the light does half the job. Late in the afternoon the stone turns warm, the rows of cypresses frame everything for you, and from the terrace you can see the whole valley.

Day one: the welcome dinner

The first evening was a welcome dinner. Some guests had landed that morning and were still a bit jet-lagged, but by dessert everyone was talking to everyone. This is what I love about weddings over more than one day. When the ceremony starts, people already know each other, and you can see it in the photos. And on the morning of the wedding, while Alyssa was getting ready, Ryan and his friends were jumping into the pool. Priorities.

The wedding day at Castello del Trebbio

Alyssa wore an off-the-shoulder satin dress. Ryan went for a double-breasted dinner jacket and a pair of embroidered loafers that I kept sneaking into my frames.

They said their vows in the castle’s stone courtyard, under the arches, with rows of black chairs tied with ivory ribbons and big bunches of orange and pink flowers along the aisle. Alyssa laughed through most of it. The kiss at the end turned into a proper dip, and someone threw petals at exactly the right moment.

For dinner, Tuscania Wedding Events and Fede Floral Design set long tables on the terrace with blue toile de Jouy tablecloths, rattan placemats, cut oranges and bunches of black grapes, with gerberas, zinnias and anthuriums in small vases. At the end of the tables there was a big floor arrangement of apricot lilies, hydrangeas and dahlias. It felt more like a long Sunday lunch in the countryside than a gala dinner, and I think that was the whole idea.

The menus were illustrated by Studio Sheean, and Just Magic Lights & Music hung the string lights over the terrace for later in the night.

Portraits at golden hour

Around sunset we left the party for twenty minutes. A row of cypresses, dry summer grass, the sun going down behind the hills. I gave them a couple of directions and then mostly let them walk and talk. Ryan spun Alyssa around a few times and she laughed so hard she had to stop.

That’s how I like to work. I’ll guide you when it helps, then I get out of the way.

  • A smiling groom in a black tuxedo holds a microphone and a book while facing a bride during a ceremony captured by a Tuscany wedding photographer. They stand in an arched stone courtyard with a guest visible in the background. Italy and Tuscan Wedding Photographer
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  • Long dining tables for a Castello del Trebbio wedding are set for an outdoor event overlooking rolling, tree-covered hills. The tables feature blue and white cloths, woven placemats, and vases of colorful wildflowers, all illuminated by string lights for a Tuscany wedding photographer. Italy and Tuscan Wedding Photographer
  • A bride and groom face each other laughing during their wedding ceremony as a smiling officiant holds a book between them. They stand in front of an arched stone doorway flanked by large, colorful floral arrangements, captured by a Florence wedding photographer. Italy and Tuscan Wedding Photographer
  • A bride with wavy blonde hair and a veil smiles lovingly at her groom during their Castello del Trebbio wedding. They hold hands in a stone hall, the groom seen from the back in a dark suit with blurred guests behind them, captured by a Florence wedding photographer. Italy and Tuscan Wedding Photographer
  • A Cartier Santos wristwatch rests inside a black velvet-lined case, a sophisticated detail often captured by a Tuscany wedding photographer. The watch features a square white dial with black Roman numerals, encased in a two-tone metal band with exposed screw details. Italy and Tuscan Wedding Photographer
  • A woman in a vibrant orange dress lifts a delicate lace veil over a bride’s head. The bride stands in a white gown before a large, arched stone doorway at a Tuscan countryside wedding, while a groom in a dark suit watches from the side amidst colorful floral arrangements. Italy and Tuscan Wedding Photographer
  • A bride in an off-the-shoulder white wedding dress and veil smiles at her groom in a sunlit stone hall, a romantic scene captured by a Tuscany wedding photographer. They stand near a slender column, softly framed by blurred pink flowers in the foreground. Italy and Tuscan Wedding Photographer
  • A bride and groom in sunglasses smile at each other on a grassy hill at sunset, captured by a Tuscany wedding photographer. She wears an off-the-shoulder cream gown and necklace, while he wears a black tuxedo with a pink flower boutonniere as sunlight creates a soft glow behind them. Italy and Tuscan Wedding Photographer

Speeches, and the sunglasses

At some point during the speeches the sunglasses came out, and from there things went a bit off script. Bride, groom and half the table ended up on their feet, cheering. It’s one of my favourite sequences of the whole season.

Day three: karaoke

On the last night there was karaoke. Nobody cared who could actually sing. No timeline, no formal moments, just friends singing together one more time before flying home.

Digital and film

I shot the weekend on digital and on film, as I do for most of my weddings. Film loves this kind of warm light, and the colours of the day, the oranges, the blue tablecloths, the gold of the grass, came out beautifully on it. You can see more in my wedding film photography gallery.

The team behind the day

Frequently asked questions

Where is Castello del Trebbio?

In Santa Brigida, near Pontassieve, in the Chianti Rufina hills. It’s about 30 minutes by car from the centre of Florence, so guests can easily stay in the city.

How many guests can you have at a Castello del Trebbio wedding?

Alyssa and Ryan had 60 to 70 guests, seated at two long tables on the terrace with room to spare. For exact numbers and indoor options, it’s best to ask the venue directly.

When is the best light for photos at Castello del Trebbio in summer?

In July the sun sets around 8:45 pm, so the warmest light is roughly between 7:30 and 8:45. That’s when I plan the couple portraits, along the cypresses and on the terrace.

Do you photograph multi-day weddings in Tuscany?

Yes, and I love them. Many couples plan a welcome dinner, the wedding day and something on the last day, like Alyssa and Ryan’s karaoke night. Covering the whole weekend tells the full story.

Do you shoot weddings on film?

Yes, I shoot on both digital and analog film. Film gives a softness that suits Tuscan light really well. I’m Federico Pannacci, and Fedepan is simply my name shortened: FEDErico PANnacci. You can find all the details in my wedding packages.

Planning a wedding near Florence?

If you’re thinking about a relaxed wedding in the Tuscan countryside, with long tables and the people you love, I’d be happy to hear about it. Have a look at my wedding photography packages, see more destination weddings in Italy, or just write to me here.