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Fabio Zito
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Vineyard proposal in Sicily: a couple on a wine picnic at Cantine Pupillo, photographed from far away between white flowers

A real story 路 Cantine Pupillo, Siracusa

Surprise proposal at a Sicilian vineyard,
she never suspected a thing.

In September Jamie wrote to me from the UK. He wanted to propose to Georgie during their holiday in Sicily, somewhere quiet and as private as possible. They had a car, so we could go anywhere.

Where
Cantine Pupillo, a winery with its own vineyards near Siracusa, and the garden of Castello Solacium
When
3 October 2026
The excuse
A wine picnic on the lawn. Georgie knew nothing.
They came from
The UK

The plan: a wine picnic at Cantine Pupillo

Jamie couldn't decide between a vineyard and the sea. I suggested a picnic at Cantine Pupillo, a well-known winery just outside Siracusa: a blanket on the lawn, a basket and a bottle of wine. A picnic at a winery is a normal thing to do on holiday, so Georgie had no reason to suspect anything.

The proposal, photographed from far away

I stayed far back, out of sight, and waited. Jamie got down on one knee on the lawn, Georgie put a hand over her face, and I took the photos from a distance without her ever knowing I was there. Surprise: done.

Surprise proposal at Cantine Pupillo, Sicily: he kneels on the lawn during a wine picnic while she covers her face The couple hugging right after the proposal at the vineyard near Siracusa

On one knee, then a very long hug.

A glass of wine, just the two of them

After the yes I left them alone for a few minutes to celebrate with a glass of wine. I kept photographing from far away, so I wouldn't break the moment. Then I walked over, introduced myself to Georgie and congratulated them both.

Newly engaged couple toasting with white wine on their picnic blanket at Cantine Pupillo

A toast, a few minutes after the yes.

No stiff poses at Castello Solacium

Then we walked a little further, into the garden of Castello Solacium, the historic castle on the Cantine Pupillo estate. No stiff poses. I gave them small ideas to keep them moving and having fun, so the joy of the moment and the looks between them stayed real, without fake poses getting in the way.

Engagement photos at Castello Solacium: he lifts her up under the stone arch Close-up of the engagement ring after the vineyard proposal in Sicily Engaged couple hugging between stone pillars in the garden of Castello Solacium He twirls her by the gate pillars of the Cantine Pupillo estate Couple laughing, sitting on the steps under the castle arch Almost-kiss under white bougainvillea at Castello Solacium Couple on the old stone staircase of the castle at Cantine Pupillo, Siracusa Holding hands against the blue Sicilian sky, seen from below Couple in front of a wooden door in the castle courtyard, framed by leaves Hug by the iron gate of Cantine Pupillo, among white flowers

The garden of Castello Solacium, Cantine Pupillo, Siracusa.

If you're planning a picnic proposal

Choose an excuse that feels normal: a picnic, a wine tasting, a walk. Let me stay far away until after the yes. And give yourselves a few minutes alone before we take any photos together.

Planning a surprise proposal in Sicily?

Tell me your date and where you're staying. I reply within 24 hours, and we'll find the right place, and the right excuse, together.

Keep reading

A Real Surprise Proposal in Ortigia: the Photo Trick → Surprise Proposal Photographer in Ortigia, Sicily → Editorial & Vintage Photoshoots in Sicily → A Real Family Photoshoot in Noto: No Boring Poses → How a Vacation Photoshoot Works (Prices & FAQ) → Photoshoot Prices in Sicily → The Best Photo Spots in Siracusa & Ortigia →
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