Last June, I flew across the pond with a good friend Kalen of Kalen Jesse Photography to second shoot one of the most magical weddings — Annaliese and Emerson’s celebration in the heart of Tuscany, Italy. There’s something about the golden summer light, rolling vineyards, and ancient stone villas that makes Tuscany feel like a dream, and this day was no exception.

A Little About Tuscany

Imagine an intimate gathering in a villa surrounded by vineyards, where your closest family and friends can soak up the Tuscan countryside — wine tastings, long dinners under the stars, the kind of slow, intentional celebration that feels more like a retreat than a typical wedding day.

Tuscany has such a deep romantic pull. Historically, it’s been a go-to for destination weddings, especially for couples from the U.S. and U.K. In fact, more than 60% of destination weddings in Tuscany are from those countries, according to data from the Centro Studi Turistici. And the numbers are still rising: bookings for destination weddings in Tuscany are projected to grow further, with a +4.9% increase in events expected. After being there for a wedding I can see why!

Capturing Their Welcome Party

Let’s start with the good stuff! One of my favorite parts of the wedding weekend actually happened before the wedding day. The couple hosted a welcome party two nights before — and honestly, it felt like the opening scene of a movie where the main characters don’t yet know their lives are about to change. The theme was red, green and white - the colors of the Italian flag and the colors of margarita pizza :) As you can see I got a little carried away with the FOOD photos!

The whole evening took place under warm string lights, long farmhouse tables, and the slow sunset and FULL moon that Tuscany does better than anywhere else. A local pizzaiolo rolled out fresh dough all night long, tossing it into the air like he’d been doing it since before any of us were born. Guests wandered up to the outdoor oven to watch their pizzas slide in, bubbling and blistering in seconds.

There were platters of the best food (because Italians refuse to do mediocre anything), glasses of local wine that kept mysteriously refilling themselves, and live musicians who played all the Italian as people mingled. It set the tone for the weekend perfectly: warm, connected, unhurried.

From a photography standpoint, welcome parties are gold. They let me meet your people before the wedding day, capture more candid interactions, and document the energy of the entire weekend instead of just the ceremony. And the details did not disappoint- reflecting the colors of the Italy flag and cherished local ingredients - Roma tomatoes and fresh basil.

Day Before Garden Brunch with Italian Yard Games

The day before Annaliese and Emerson’s wedding began exactly the way a destination celebration in Tuscany should: slowly, intentionally, and surrounded by the people they love most. Hosted in a lush garden setting, their welcome brunch felt more like a long European afternoon than a formal event—easy conversation, soft laughter, and plenty of time to simply be together.

The palette was entirely green, echoing the olive trees and rolling hills nearby, and setting the tone for a weekend rooted in nature and connection. Guests sipped espresso and spritzes while playing classic Italian yard games, drifting in and out of conversation as the sun moved across the garden.

There was no rush, no schedule to keep—just the quiet magic of everyone arriving, settling in, and realizing they were about to experience something special together. It was the perfect prelude to the wedding day: relaxed, joyful, and deeply present.

Capturing Their Day: Through My Lens

From the moment I arrived, I was struck by how grounded and present Annaliese and Emerson were. They weren’t just having a wedding — they had currated a long weekend of memories for themselves and their loved ones.

Getting ready and First looks: Everyone was staying at the villa Divole which made it easy for Kalen and I to bop around from Annaliese to Emerson. Annaliese did a little first look with her dad before doing one with Emerson.

Ceremony: The ceremony was held outside, overlooking vineyards that stretched into the distance. The light in June Tuscany is — warm and golden, especially as the sun began to dip.

Portraits and Cocktail Hour: After the cocktail hour, we wandered through olive groves and vineyards. I loved how relaxed Annaliese and Emerson were. We captured them laughing under cypress trees, slow dancing on a sun-dappled path, and stealing a quiet moment with a sweeping Tuscan vista behind them.

Details: The planner Giulia and her team did an amazing job with all the details. When you plan a wedding from afar it’s so hard to know how everything will come together and it was perfect.

Reception: For dinner, we moved to a courtyard with a long banquet table draped in linen, local flowers, and candles. Guests toasted with Chianti, and my favorite - a live saxophone player. Which I now want at every wedding. Some toasts were made spontaneously throughout the evening and we got to steal them away for a few sunset photos nearby.

Tips for Planning a Wedding in Tuscany (from a Photographer’s POV)

If you’re dreaming of saying “I do” in Tuscany — or anywhere overseas — here are some of the lessons I’ve learned (and things I wish more couples asked me upfront):

Hire a local planner.
There’s a reason most couples go this route: language, logistics, vendor sourcing. Tuscany’s wedding market is mature — +52% of couples now use a wedding planner. A local planner can help with legal paperwork, recommend trusted florists and caterers, and keep everything running smoothly.
Plan for more than one day.
Destination weddings in Italy often become multi-day celebrations. Around 18.8% of couples opt for a “wedding week” that includes guided tours, welcome dinners, and rehearsal dinners. This isn’t just a wedding — it’s an experience for you and your guests.
Time your photography for golden hour.
If your ceremony is during the day, think about scheduling a portrait session in the golden hour that evening.
Be clear on your guest list and accommodations.
Since many venues are villas, castles, or estates, you’ll probably need to coordinate lodging for guests. That means thinking early about who’s coming, where they’ll stay, and how to move people between events. Give your guests a far enough heads up and make sure they RSVP early.
Budget for the “extras.”
In Tuscany (or Italy in general), couples tend to spend more on food and drink (hello, amazing Italian cuisine + wine) — almost a third of the budget often goes to F&B. And don’t forget travel costs, staffing, and possibly guest transport.
Embrace local vendors.
Using local florists, musicians, and artisans not only supports the region but also helps with authenticity. The florals will feel like they belong in Tuscany, the food will be seasonal, and the whole vibe will be rooted in place. But of course, if you want to fly out your photographer - that’s fine lol.
Legal vs symbolic ceremony.
Many couples do a symbolic ceremony in Italy for the aesthetics and emotional experience, then handle the legalities in their home country. This simplifies paperwork, and you still get the magic of a Tuscan wedding.

Some bonus film shots

The Takeaway: Is It Worth It? (Yes, Yes, Yes)

From where I stood — camera in hand, chasing golden light — Annaliese and Emerson’s Tuscan wedding was everything I hope for when I travel for a couple’s big day. It wasn’t just about the scenery (though, wow, the scenery) — it was about connection. Their wedding felt like a gathering of their community, held in one of the most romantic places on earth.

If you’re dreaming of a destination wedding, especially in a place as timeless as Tuscany, I’d love to work with you. I’ve photographed weddings across Colorado and flown to Italy for shoots like this one, and nothing makes me happier than helping couples freeze moments that feel both cinematic and deeply real.

VENDOR TEAM:

Planning & Design: @giuliaalessandri

Photography: @kalenjessephotography_co

Second Shooter: @kateivyphotography

Florals: @lucacozza_flowerspecialevents

Venue & Catering: @dievole

Audio & Lights: @kaleydo.official

Ceremony & Aperitif Music: @biancalanimatteo

Party Music: @fixthemusic + @supersonic.band

MUA: @samanthapretto_hair_and_makeup

Stationery: @chiaramadastudi

Rings: @anthony_ms_visions_in_gold