How we're managing 75 guests across 15 apartments in Tuscany

by Martin Haas

Last updated: April 2026

My fiancee Sarah and I are getting married this August at Le Filigare, a wine estate in the Chianti hills of Tuscany. 75 guests. Four days. Fifteen apartments scattered across the property. Guests flying in from the United States and Austria. Two languages minimum, more in practice.

If that sounds like a logistical nightmare, you're not wrong. But we're about four months out now and I can honestly say it's been manageable. Not easy - manageable. I want to share what's actually working for us, because when I was looking for advice on managing destination wedding logistics at this scale, most of what I found was either too vague ("just make a spreadsheet!") or clearly written by someone who'd never done it.

This is the real version.

The venue: why 15 apartments changes everything

Le Filigare isn't a hotel. It's a working wine estate with apartments and villas spread across the grounds - think converted stone farmhouses with names like Acero, Ginepro and Castagno. There are 33 individual rooms across 15 units, each with different configurations: some have extra bed options, some have private bathrooms, some share. Some are a short walk from the main event space, others are a longer stroll through the olive groves.

This is very different from a hotel block where you just tell guests to call the Marriott and use code MARTINANDSARAH. We had to assign every guest to a specific room in a specific apartment. That means knowing who's traveling together, who can share a bathroom, who needs a cot for their baby, who needs an extra bed for their kid and who absolutely cannot be in the apartment next to their ex.

We spent weeks on room assignments. Sarah had a color-coded spreadsheet that looked like a flight manifest for a small airline. And then, of course, people changed plans. Someone dropped out, a couple decided to bring their toddler after initially saying they'd leave him with grandparents and two guests who we'd put in the same apartment turned out to have some drama we didn't know about.

The two-country problem

Our guest list is split roughly in half between the US and Austria. Sarah's family is American. Mine is Austrian. That creates a few challenges that couples with a single-country guest list don't face.

First, language. Most of our Austrian guests speak English, but their comfort level varies. My grandmother, for example, speaks Finnish and German but not a word of English. My uncle's partner speaks mostly German. Some of Sarah's college friends only speak English and Spanish. When you're sending logistics information - shuttle times, payment details, schedule changes - you can't just blast it out in one language and hope for the best.

Second, phone numbers. International texting is a mess. If you text an Austrian phone number from a US number, it might work, it might not and either way it'll look unfamiliar and possibly get filtered. Same going the other direction.

Third, currency. Our venue quotes in euros. Our American guests think in dollars. Payment links need to make sense to both groups without manual conversion.

I ended up setting up two phone numbers for guest communication - a US number (+1) for North American guests and an Austrian number (+43) for European guests. When a guest texts, the system detects which country they're in based on their phone number and routes them to the appropriate local number. A Finnish number gets the Austrian line. A Canadian number gets the US one. Guests just see a local-looking number in their messages.

What guests actually need to know (and when)

I made a mistake early on that I think a lot of destination wedding couples make: I tried to communicate everything at once. One massive email with the schedule, the venue details, the accommodation info, the excursion options, the payment links, the shuttle times, the packing suggestions. It was thorough. Nobody read it.

Here's what I learned about timing information delivery for a Tuscany destination wedding with 75 guests:

Six months out: the basics

Dates, location, nearest airport (Florence or Pisa, both work) and a rough cost estimate. That's it. People need to book flights and request time off. They don't need to know the shuttle schedule yet.

Three months out: money and rooms

This is when we sent room assignments and the first payment information. Our guests need to pay for their accommodations and can optionally sign up for excursions - a wine tasting at the estate, a day trip to Florence and a Tuscan cooking class. Each of these has its own cost.

We found that payment collection is one of the most awkward parts of a destination wedding. You're asking your friends and family to pay for something, which already feels weird and then you have to track who's paid and who hasn't and then send reminders to the people who haven't, which feels even weirder.

What ended up working: personalized payment links sent via text message. Each guest (or couple) gets their own link for each item they owe. They tap it, pay on their phone and it's done. I can see in real time who's paid and who hasn't, without having to chase anyone through Venmo or ask them to wire money to an Italian bank account.

One month out: logistics

Shuttle schedules, arrival coordination, the detailed day-by-day schedule, dietary preference collection. This is when things get granular and this is when guest questions really ramp up.

Day-of: everything, all at once

"What time is the ceremony?" "Where do I go for dinner?" "The bus was supposed to be here at 3." "My room key isn't working." "Is there Wi-Fi?" "Where's the nearest pharmacy?"

During the wedding itself, you cannot be the person answering these questions. You're getting married. Your wedding party is busy. Your parents are emotional. Someone needs to be available to handle the small stuff and that someone cannot be you.

How I solved the communication problem

I'm a developer, so I did what developers do - I built something. Vino is an SMS concierge I built originally just for our wedding. Guests text a phone number and get instant answers to their questions. Not canned auto-replies, but actual helpful responses based on all the information we've loaded about our wedding - the schedule, the room assignments, the shuttle times, the venue details, the excursion info.

Here's what makes it work for a 75-guest destination wedding with 15 apartments:

Every guest gets personalized answers

When a guest texts "what room am I in?", they get their specific room assignment - the apartment name, the room within it, whether it has a private or shared bathroom, the bed type. They don't get a generic "check the spreadsheet" reply. The system knows who they are based on their phone number and pulls up their specific information.

This is surprisingly important. At a venue like Le Filigare, where there are 33 rooms across 15 apartments, generic information doesn't help. A guest in Castagno needs different directions than a guest in Acero. The shuttle pickup might be closer to one apartment than another. Telling everyone "the shuttle leaves from the main building" only works if everyone knows where the main building is relative to their apartment.

Payments without the awkwardness

I set up payment links through Stripe for each item - accommodation, wine tasting, Florence trip, cooking class. When a guest texts "pay" or asks about payments, they get a list of everything they owe with one-tap payment links. When they pay, it's recorded instantly. I can see it in the admin panel. Their party members (spouse, partner) also get marked as paid for shared items, so I'm not double-billing couples.

The best part: I never have to send an awkward "hey, you still owe us for the room" text. The system handles reminders. I set due dates for each payment item and the broadcast feature lets me send payment reminders to everyone who hasn't paid yet - with their personalized amounts and links included. It feels less personal and more professional, which makes the whole money conversation much less uncomfortable.

Broadcast without the chaos

Group chats are terrible for wedding logistics. I've been in destination wedding group chats before. Someone asks about the shuttle. Three people respond with conflicting information. Someone makes a joke. Someone else sends a meme. The actual answer gets buried and four more people ask the same question the next day.

Instead, I send broadcast messages - one-to-many communication where each guest gets a personal text message. It looks and feels like a personal text, not a mass blast. I can target broadcasts to specific groups: all guests, just the guests who signed up for the wine tasting, just the guests arriving on Thursday, or just guests who haven't paid yet.

And when guests reply to a broadcast - because they will - they're replying to the concierge number, not to a group chat. Their question gets answered immediately and privately, without cluttering up everyone else's phones.

Languages just work

This was the feature I was most proud of building. When my grandmother texts the Austrian number in Finnish to ask about dinner, she gets a reply in Finnish. When Sarah's dad texts from Ohio about the shuttle, he gets a reply in English. When our Italian-speaking friends ask about the cooking class, they get Italian. Nobody has to switch languages or use a translator app.

For broadcasts, I write the message once in English and have it automatically sent in the appropriate language to each guest. So one broadcast about the shuttle schedule goes out as English to the Americans, German to the Austrians, Finnish to my grandmother and so on. I don't have to write the same message six times.

The excursion coordination problem

We're offering three optional excursions during the wedding week: a wine tasting at the Le Filigare estate itself, a day trip to Florence (about an hour's drive) and a Tuscan cooking class. Each has a different price, a different capacity and guests need to sign up and pay in advance so we can coordinate transportation and reservations.

This seems simple until you realize: you need to know headcounts to book the restaurant in Florence, but guests are indecisive. You need to arrange transportation based on who's going, but people sign up at different times. And you need to collect payment before the event, but some guests forget until the day before.

The system tracks excursion signups automatically. When a guest says "I want to do the wine tasting," it's recorded. When they pay, it's confirmed. I can pull up a real-time list of who's signed up and paid for each excursion at any time, which means I can give the venue accurate headcounts without manually reconciling a spreadsheet.

What about photos and memories?

One thing I added that I didn't originally plan for: photo sharing and voice memories.

For photos, each guest gets a personal link to upload pictures. During the wedding weekend, guests take photos on their phones and can text them to the concierge number or use their upload link. All the photos end up in one place - no chasing people for photos after the wedding, no "can you AirDrop me that picture?" at the reception.

For voice memories, each guest gets a link to record a voice message - a toast, a memory, well wishes, whatever they want to say. These recordings can be pressed onto a vinyl LP as a keepsake. The idea is that years from now, we'll be able to put on a record and hear our friends and family's voices from the wedding. Sarah almost cried when I showed her this feature, which is how I knew it was a good idea.

The admin side: what the couple actually sees

Behind the scenes, Sarah and I have a dashboard that shows us everything at a glance: how many guests have confirmed, how many have paid, arrival and departure dates, room assignments, excursion signups and a live activity feed of what's happening (new guest messages, payments received, photo uploads).

We can make changes on the fly - reassign a room, adjust a payment amount, update the schedule - and the information guests receive updates immediately. When a guest texts "what room am I in?" after a room swap, they get the new room, not the old one.

The dashboard also handles the awkward stuff automatically. Payment reminders, schedule changes, arrival coordination. I can compose a broadcast message, preview exactly what each guest will see (including their personalized details and correct language) and send it with one click.

Things I wish I'd known earlier

1. Start collecting flight information early

We needed arrival and departure times to coordinate airport shuttles and check-in logistics. Getting 75 people to tell you their flight details is like herding cats. Start asking three months out, not three weeks. And make it easy - a guest should be able to text "arriving Thursday at 2pm on Delta 487" and have it recorded automatically, not fill out a Google Form.

2. Parties are your unit of organization

Don't think in terms of individual guests. Think in terms of parties - couples, families, friend groups traveling together. A party shares a room (or rooms), shares payment responsibility and communicates as a unit. When one person in a couple pays for their room, both should be marked as paid. When you send a payment link, both phones in the couple should receive it.

Our 75 guests break down into roughly 35 parties. Managing 35 parties is much more tractable than managing 75 individuals.

3. Kids and babies need tracking too

We have several families with children and babies coming. Kids don't have phones and won't interact with any communication system, but they still need beds, they still affect room assignments (cots, extra beds) and they still count for headcounts at meals and excursions. Track them as party members, not as guests.

4. The last two weeks are the busiest

Guest questions follow a hockey stick curve. You'll get a trickle of questions for months, then a flood in the final two weeks as the trip becomes real and everyone suddenly has urgent questions about luggage, weather, dress codes and whether they need an adapter for their phone charger in Italy (yes, they do - Type L or Type C).

Whatever system you use, make sure it can handle that surge without requiring you to be glued to your phone during the last two weeks of wedding prep, when you have a thousand other things to do.

5. Not every guest texts

Some of our guests - particularly older relatives - don't text much or at all. That's fine. The system is there for the guests who want it. For the ones who don't, we have a couple of family members who serve as information relays. Aunt Petra knows everything and will happily tell anyone who asks. Every wedding has an Aunt Petra. Find yours and make sure she has all the information.

Is it actually working?

We're about four months out as I write this. Here's where we stand:

• All 33 rooms assigned across 15 apartments
• About 70% of accommodation payments collected
• Flight information received from roughly 60% of guests
• All three excursions have solid headcounts
• Zero unanswered guest questions (the concierge handles them instantly)
• Sarah and I have spent maybe 2-3 hours total on guest communication in the last month

That last point is the one that matters most. We're planning a four-day wedding in another country and guest communication is not the thing keeping us up at night. The catering, the flowers, the timeline, the weather - sure, those keep us up. But "did everyone get the shuttle schedule?" is not a question we have to think about. It's handled.

I built Vino for our wedding because I couldn't find anything else that did what we needed - personalized, multilingual SMS communication with integrated payments, room assignments and photo collection. After building it, I realized other couples planning destination weddings have the exact same problems we had. So I turned it into a product.

But honestly, the specific tool matters less than the principle: you need a system for guest communication that doesn't require you to be personally available 24/7. Whether that's a dedicated wedding planner, a very organized maid of honor, or a purpose-built tool - get the guest logistics off your plate so you can focus on getting married.

August can't come soon enough.

More wedding planning guides

• Planning a wedding in Tuscany
• Destination wedding logistics checklist
• How to collect payments from wedding guests
• Multilingual wedding communication
• How to communicate with destination wedding guests

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