An October Evening to Remember:Hannah & Brandon at Tenuta di Sticciano

An October Evening to Remember:
Hannah & Brandon at Tenuta di Sticciano

There are destination weddings in Tuscany that go beautifully to plan, and then there are those that take on a life of their own — where the energy builds into something you couldn’t have scripted. Hannah and Brandon’s October destination wedding in Tuscany, at Tenuta di Sticciano in the Valdelsa hills near Certaldo, was firmly and gloriously the latter.

Eighty-five guests traveled from across the Atlantic to be part of it. What they got was a full weekend — a welcome party, a ceremony in the Tuscan countryside, a candlelit dinner, and a party that nobody is going to forget in a hurry.

The Venue

Tenuta di Sticciano is the kind of place that makes you understand why people fly across an ocean to get married in Tuscany. Approached along a long cypress-lined drive, the estate announces itself with absolute confidence and no hurry at all. The villa is a classic of its kind: pale stucco, grey shuttered windows, a stone family crest above the entrance, a small chapel tucked into the ivy at the garden’s edge.

October is when this part of the Valdelsa is at its most cinematic. The harvest is in, the hills turn amber and gold, and the light does things to stone that no photographer needs to enhance. For Hannah and Brandon, the venue was never just a backdrop — it was central to the vision of what the weekend should feel like.

The Evening Before: Spritzes, Spaghetti & a Vintage Cinquecento

The weekend began the night before the wedding with a welcome party built around the most Italian brief imaginable. The signage said it plainly — Spritzes & Spaghetti — and nobody needed further convincing. Blood orange garnishes, fresh herbs, a bar with gold-striped linen set up in the garden: convivial and deliberately uncomplicated, exactly what a group of jet-lagged North Americans needed to remind themselves that they were, in fact, in Italy now.

The addition of a powder-blue vintage Fiat 500 gelato cart parked on the gravel tipped the evening from lovely into memorable. Hannah — Aperol spritz in hand at the Tuscan sunset — looked like she had been born for this exact moment.

The Details: Gifts, Florals & the Table

The welcome gifts — woven straw totes with tan leather handles, lined up along the garden wall in the last of the afternoon light — were one of those details that guests noticed immediately and kept all weekend. Thoughtful, beautifully local, and thoroughly Tuscan.

The Ceremony

The ceremony was held outdoors in the grounds of the estate — one of those settings that makes you wonder why anyone would ever choose to marry inside. The Tuscan hills rolled out in every direction, the October sky was a deep, guileless blue, and the stone pines threw long shadows across the lawn. Guests settled into crossback chairs in the afternoon sun while Two Strings played beside the arch.

Violamalva built a tall asymmetric floral arch — white hydrangeas, garden roses, dahlias, blush and peach tones trailing into greenery — romantic and lush without being heavy. When Hannah and Brandon faced each other at the altar with the Valdelsa valley spread behind them and their guests watching in silence, it was the kind of moment a planner quietly exhales at.

Portraits

Between ceremony and dinner, Morina Photo took the couple through the estate — along the cypress drive, against the October ivy wall turning from green to deep red, through the golden light of the olive grove. These are the photographs that happen when a venue has real soul and a couple is genuinely happy.

The Table

As the light dropped, the table came into its own. Kitchen Wishes had laid a long communal table along the facade of the villa — crossback chairs, linen runners, tapered candles, and Violamalva’s florals in loose clusters of blush, peach, and white down the center. Tall floral columns flanked the arched doorway of the villa behind. The whole composition caught the last of the golden hour as if it had been designed specifically to do so — which, of course, it had.

Hannah stepped out through the arched doors into the scene she had planned for months, and the look on her face said everything.

Dinner

Kitchen Wishes did what great Italian catering always does: made the food feel like the point of the evening. Cacio e pepe arrived table-side with fresh truffle grated directly onto each plate. Waiters emerged through the arched doors in procession. Mixar’s lighting made the Tuscan night — strung with lights, alive with conversation — look like something from a film. The toasts were warm, the wine was excellent, and at some point during the speeches every napkin at the table went up at once.

The Party

Then the music changed, and the evening became something else entirely.

Hannah reappeared in a second dress — a short, pearl-embroidered mini — and the message was clear: we are not done yet. The wedding cake, a spectacular berry-topped tart, was cut to the thunder of cold fireworks. The first dance happened under string lights on the stone courtyard. Then the party moved inside, the DJ and Two Strings took over, and the dancing started properly.

Espresso martinis arrived with stroopwafels balanced on the rim. The cannoli came out mid-floor and were delivered directly and enthusiastically into guests’ mouths. Hannah was lifted onto a guest’s shoulders and showed the room exactly how a bride ends a wedding in Tuscany.

Planning Your Own Wedding at Tenuta di Sticciano

Tenuta di Sticciano is a working Tuscan estate with genuine character — which also means it rewards a planner who knows how to work with the space, the light, and the local vendors who understand it. October is a beautiful month to marry in this part of Tuscany, but a popular one. The best venues in the Valdelsa fill up well in advance.

If you are considering Tenuta di Sticciano — or any estate in the Certaldo, Chianti, or Valdelsa area — we would love to talk through what is possible. We have been working in this territory for over a decade and know it well.

Wedding Credits

• Planning Tuscan Wedding by Jill Romanelli
• Venue Tenuta di Sticciano, Certaldo, Tuscany
• Photography Morina Photo
• Florals Violamalva
• Catering Kitchen Wishes
• Music Two Strings
• Lighting Mixar
• Season October
• Guests 85