A Three-Day Wedding Weekend at Castello di Vicarello, Tuscany | Anna & Chani

CHEERS OUR GIRLS
Castello di Vicarello, Tuscany

Anna and Chani’s Castello di Vicarello wedding was never meant to be a single day. They wanted a weekend: three days with their closest people, in a place where food, nature and quiet luxury sit together. They found it at Castello di Vicarello, a medieval castle in the province of Grosseto, in southern Tuscany, surrounded by centuries-old olive trees.

In February 2026, Vogue Italia dedicated a Real Weddings feature to their celebration, photographed by Rosita Lipari. We filmed the whole weekend, from the first dinner to the last swim, and this film is how we remember it.

Southern Tuscany feels different from the Chianti postcard. The hills are wider, the light is softer, and the castle keeps a calm that suits couples who prefer atmosphere over spectacle. Castello di Vicarello gives you a historic setting, a working kitchen garden, olive groves and vineyards, and enough space to host a full weekend rather than a single event.

If you are comparing venues, our guide to finding the best wedding venue in Italy covers other options, and our luxury wedding in Tuscany page explains how we approach filming here.

The weekend opened with a welcome dinner: pasta, Italian music and a table dressed with tomatoes, basil and rosemary. It set the tone for everything that followed, relaxed and generous, with guests who already felt at home. A welcome dinner is one of the best ways to start a destination wedding, and we wrote about why it matters.

The ceremony took place in the castle’s kitchen garden, between olive trees and vines, led by a close friend of the couple who flew in from Los Angeles. Their mothers opened it together, an unconventional gesture that said a lot about the day. Chani’s nephew read a poem and walked with Benzo, the couple’s dog.

Anna and Chani both wore Victoire Vermeulen: two different silhouettes, one shared sense of ease. The floral design leaned on vegetables as much as flowers, which suited the setting and the couple.

After the ceremony came an aperitivo inspired by Italian markets, then an outdoor dinner with sculptural florals, fruit, candles and string lights. Anna and Chani danced first with their fathers, and then The Shakes played live, followed by DJ Cale, with pizza at midnight for the guests who were still dancing.

The weekend closed with a brunch by the pool, played in yellow: lemons, stripes and a vintage Ape Piaggio serving gelato. It was light, funny and the right ending for three days that never felt formal.

Planning was by Nicole Alexandra Designs, photography by Rosita Lipari, and florals by Harvesia Floral. Film by Echo of Journey.

Three things made this weekend work, and they apply to most Tuscan destination weddings:

1. Plan the weekend, not the day. A welcome dinner, a ceremony day and a brunch give guests time to enjoy the place, and give the film a natural structure.
2. Choose a venue that has its own character. Here the kitchen garden, the olive grove and the pool each became a distinct setting.
3. Work with a film team that knows the venue’s light. Late afternoon in an olive grove and midday by a pool call for different decisions.

If you are dreaming of a wedding in Tuscany, or anywhere in Italy, and want it filmed as a story rather than a record, we would love to hear about it. REACH OUT to book a consultation or a call.