A Tuscany Wedding Weekend

Sep 4

Michael & Darrin's Three-Day Celebration in San Gimignano & Chianti

Michael and Darrin’s Tuscany elopement and intimate wedding weekend was a three-day celebration built around being present with the people closest to them. Instead of squeezing everything into one wedding day, they gave each part of the weekend room to breathe and made everyone feel like they were sharing one big, memorable vacation together.

Planned with The Greatest Adventure Weddings & Elopements, their celebration began at Locanda Le Piazze, a luxury boutique hotel in Chianti, where they exchanged vows in an intimate, elopement-style ceremony. From there, everyone gathered at Il Segreto di Pietrafitta (The Secret of Pietrafitta), a private villa near San Gimignano, where friends and family stayed on-site for a few days. They embraced Tuscany's slower pace, filling the weekend with poolside drinks, homemade pizza, long dinners, gelato, games, and dancing while taking full advantage of everything this incredible region had to offer.

As their wedding photographer, I had an absolute joy capturing their entire wedding experience. I loved how the weekend gave everyone the space to simply be present. Day one gave them quiet. Day two gave everyone space to embrace “la vita dolce” with a pool party. Day three was a full celebration. A balance only wedding weekends can make possible.

A Tuscany Wedding Weekend That Felt Like a Vacation

Michael and Darrin knew they wanted something intimate and intentional. Instead of cramming everything into one overly busy day, they chose to spend these special moments the way they wanted, with the people they wanted present. The private ceremony stayed close and personal. The welcome party felt relaxed and social. The reception gave everyone a reason to gather around long tables, stay late, and enjoy the villa together. I really appreciated how they carved out dedicated time to be alone, to be with their closest family, and still celebrate with all the friends who traveled to be there. An experience built around thoughtfulness and focused on what matters most; exactly what we love to be a part of.

An Intimate Ceremony With Their Moms

Michael and Darrin began their first day by getting ready and sharing a first look with each of their moms (such a sweet and thoughtful moment), followed by an elopement-style ceremony in a beautiful olive grove with just the four of them. It felt peaceful and grounded in the best way. Every part of the experience reflected what mattered most to them: privacy, intention, and the chance to be fully present with the people they love. After the ceremony, they had lunch at Poggio Amorelli Winery, then took photos while exploring San Gimignano. While the day was well planned, it still felt true to them. They enjoyed walking and talking, eating and drinking, and taking in the Italian summer together.

Poolside Welcome Party and Sunset Portraits

The second day brought everyone together at the villa for a pool welcome party. This was when the weekend started to feel like a shared vacation. People were in the water, sitting in the sun, catching up over drinks, and settling into Tuscany together. I kept noticing how easy the whole day felt, which is exactly what a destination wedding weekend can do when the timeline is that relaxed. Later, we stepped away for sunset portraits around the property. One thing I love about multi-day weddings is the time and space for gorgeous couples’ portraits in a variety of settings without pulling away from the celebration for too long. Looking over Michael and Darrin’s gallery, they’ll have so much to look back on and smile about for years to come.

Dinner, Gelato, Games, and Dancing at a Private Villa

Day three was the full wedding celebration at the villa, planned with Erika of The Greatest Adventure Weddings & Elopements, who did an incredible job bringing everything together! Reception details were layered throughout the property: portraits with a classic Fiat outside the villa, long tables for dinner, gelato, Luna Park games, and dancing once the sun went down. It had all the energy of a wedding, but since the ceremony had already taken place privately, the evening felt even more relaxed and fun.

Why This Multi-Day Wedding Worked So Well

For Michael and Darrin, what made their celebration so memorable wasn't the number of days. It was how intentionally they spent them. By choosing a multi-day wedding, they gave themselves the freedom to slow down, be fully present, and experience each part of the celebration without feeling like they had to fit everything into a single day.

That's where a multi-day wedding truly shines, especially in a beautiful destination like Tuscany. Instead of rushing from one event to the next, you have time to settle in, connect with the people you've invited, and enjoy the place you've traveled so far to experience. The wedding becomes more than a single day. It becomes a shared experience you'll remember long after the celebration ends.

If you're planning an intimate Tuscany wedding or a multi-day wedding weekend anywhere in the world, I'd love to hear what you're envisioning and help document your celebration.