Play Hard · Weddings
I planned a destination wedding in Croatia — on a yacht, no less — and lived to tell the tale. Actually, more than lived: it was the best week of my life. But there are things I learned the hard way (and a few I got right on purpose) that nobody tells you before you book that flight. Here they are.
Your location isn't just a backdrop — it will change and dictate everything. The season, the budget, the guest list, the vendors, the legal logistics, the timeline. Every single decision downstream flows from this one.
So choose soon, and choose wisely. Don't just pick the place with the prettiest Pinterest photos (though let's be honest, that's how it starts). Ask yourself: Can my people actually get there? Are there vendors on the ground? What's the weather doing that month? Once you lock in the location, everything else has a framework. Until you do, you're just planning in circles.
Here's what nobody warns you about: the moment you announce a destination wedding, you become a travel agent. Your guests will ask about flights, connections, transfers, costs, and whether they need a visa — and the more you know, the more considered and cared for they'll feel.
Brainstorm the whole journey from their front door to your venue: mode of travel, difficulty, price. Then think honestly about your guest list's travel experience — or lack thereof. A confusing multi-leg journey that's no big deal for your backpacker college roommate might be genuinely overwhelming for your grandmother who's never left the country. If the travel is difficult or confusing, over-communicate. Send guides. Suggest flight routes. Your guests aren't wedding planners, and they didn't pick the destination — you did. Make it easy for them to say yes.
There's a massive difference between an all-inclusive wedding venue and a "figure it out yourself" venue, and nobody tells you this until you're in it.
An onsite venue, a church, or a dedicated wedding venue comes with staff, packages, and answers. An Airbnb, a villa, a boat, or any non-wedding venue means you are sourcing every rental, every vendor, and every logistic — and coordinating all of it. Now add the destination layer: you're coordinating from a different country, possibly in a different language, across time zones, with vendors you've never met.
Neither option is wrong. But know which one you're signing up for, because it determines whether your planning process is "review the packet" or "run a small international operation."
If you take one thing from this post: get a local planner. Not someone from home who's "done destination weddings" — someone who lives and works where you're getting married.
Their local geography, culture, and connections are everything. They know which vendors actually show up, what's realistic on the ground, which laws and customs you don't even know you don't know, and — crucially — they speak the language.
This sounds like a contradiction. It's not. It's the whole secret.
I over-planned my wedding. And I also planned to be flexible. Those two things worked together: because I had thought through everything, when things inevitably went sideways I either (a) had multiple backup plans ready to deploy, or (b) could genuinely just let it go — because everything else was so dialed in that one hiccup couldn't touch the day.
Flexibility isn't the absence of planning. Flexibility is a luxury that thorough planning buys you. Which leads directly to...
Something will go wrong. At a destination wedding, I'd almost guarantee it. The question isn't if — it's how you respond.
Here's mine: my dad's luggage — with his tux in it — went missing at the airport and never made it to Croatia. The day of my wedding. In a foreign country. On a national holiday, when everything was closed.
My planner pulled off the impossible: she got a suit shop to open on a national holiday and fit my dad for a brand-new suit the morning of my wedding. (See #4. This is what local connections mean.) What could have been a meltdown became one of our favorite stories from the whole week. And because this was the major thing that went sideways (instead of 100 little things I forgot to plan for), I was oddly calm, cool, and collected even after I was told “he can wear shorts and a t-shirt to walk you down the aisle if it comes to it.” No. No he can’t. He won’t. And he didn’t. He did wear that for our father-daughter dance, but you can’t win ‘em all folks! Let the little things go!
Something will go wrong at your wedding too. Decide now that you're going to be okay with it, pivot, or fix it.
This ties everything together, especially #4 and #5. The entire point of planning so thoroughly and putting the right people in charge is this: so that on the day, you stop worrying about logistics entirely and just enjoy the moment.
You planned for months. You flew across the world. The people you love most flew across the world for you. Don't spend the day managing — you already did the managing. Hand it off, be present, and take it all in. It goes so fast.
Nobody tells you that a legal marriage abroad can involve residency requirements, apostilled documents, translations, and bureaucratic timelines that vary wildly by country. Many destination couples quietly handle the legal paperwork at home — a simple courthouse signing before or after — and treat the destination ceremony as the real wedding. There's no wrong answer, but figure it out early so it's a choice, not a scramble.
Group texts and email chains will bury you. Create one central place — a wedding website or guest portal — where everything lives: travel guides, itineraries, packing lists, dress codes, FAQs, currency and payment tips (pro tip: check whether your credit cards are even widely accepted where you're going — Amex was spotty in Croatia!). Then update it relentlessly. Your guests will feel taken care of, and you'll answer each question once instead of thirty-three times.
I literally built a completely custom interactive guest portal for my wedding week — the "Corlett Yacht Club" — which you can check out here.
Planning your own destination wedding? Drop your questions in the comments — and if you want the full story of how we pulled off a week-long yacht wedding in Croatia, stay tuned.
It's in the works — we're building the community first. Join now and you'll be in the room early: the real lessons behind the trips, where I'm going next, and the bits I'd only put in an email. One a week when it launches.