Everyone loves the idea of a dreamy destination wedding—turquoise waters, toes in the sand, and the clink of champagne flutes at sunset. But behind those Pinterest-perfect photos are stories most couples never hear.
As someone who’s planned over 1,500 destination weddings, including several for celebrities, I’ve seen it all: barefoot vows on the beach, elephants at receptions, and—yes—even grooms arriving on what can only be described as a pantomime cow. Destination weddings can be magical, meaningful, and often more affordable than weddings at home. But let’s not pretend they always go to plan.
I know this from personal experience—because my own destination wedding didn’t go exactly as planned either.
My own wedding: Blooms, boats, and a bucket of roses in Venice
Long before I became a professional wedding planner, I planned my own destination wedding—on a cruise ship sailing into Venice.
I had it all worked out: we were docking for an overnight stay, and I’d use that time to dash into Venice the day before the wedding and buy fresh flowers to make my own bouquet and arrangements.
Simple, right?
Except when we arrived on that Wednesday, Venice was observing a public holiday—and everything was closed.
Panic set in.
Determined not to get married empty-handed, I made my way to St. Mark’s Square, where I found a woman selling roses individually at eye-watering prices. I bought her entire bucket of roses, no questions asked. Then I wandered through hotel lobbies until I spotted a few floral arrangements that looked somewhat abandoned (and possibly about to be changed out). I struck deals, charmed bellboys, and cobbled together enough blooms to bring back on board.
And that’s how I ended up getting married in Venice with a DIY bouquet made from St. Mark’s roses and a few pilfered petals from hotel lobbies. Not exactly textbook—but memorable, meaningful, and very me.
The mandap makeover nobody asked for
At one elaborate Indian wedding with 140 guests, we built the couple's custom mandap—an ornate ceremonial altar—beginning at 6:00 a.m. for their 9:00 a.m. ceremony. At showtime, the only people seated were two polite Canadians, sitting alone in front of our masterpiece.
Then the trickle of guests began, followed by the grandmothers—two determined matriarchs who arrived carrying giant black bin bags filled with shiny gold trinkets, silk flowers, plastic garlands, and various kitschy decor they'd brought from local markets. Their mission? To "enhance" the mandap.
Unfortunately, we had to inform them that we were under very strict instructions from the bride and groom, and absolutely none of their decorations could be used. I still recall the crestfallen look on their faces—followed swiftly by death stares and muttered disapproval for the rest of the day.
The horse that became a pantomime cow
One of my all-time favourite disasters was, once again, at an Indian wedding. The groom was supposed to make a grand entrance on a majestic white horse. We'd booked it a year and a half in advance.
But on the morning of the wedding, a brown horse arrived, barely larger than a donkey.
I asked the handler what was going on.
“White horse, he no happy,” he said with a shrug.
Before I could clarify, he turned and started to leave with the horse.
Panicking, I chased after him—“No, no! We still need a horse! But is there any way to get the white one?”
He just shook his head.
Out of options, I sent my son to borrow a white sheet from housekeeping. He returned with a king-sized one, and together we tried to wrap the horse. Between the flapping fabric, the confused handler, and a horse that wanted no part of it, the result looked more like a pantomime cow than a majestic steed.
The knots under its belly were tight, and when we realized the groom had seen it, we frantically tried to remove the sheet—but the angry horse wasn’t having it.
The groom stormed over. “What is this?”
And, with no better explanation, I stammered: “White horse… he no happy.”
Let’s just say: he was not amused.
When karma books the wedding venue
We once had a bride who was, by all definitions, a bridezilla. She was rude to my entire team every time she called. Nothing was ever good enough, and every call felt like we were auditioning for a part she had already cast us out of.
Despite all this, we planned the wedding down to the last detail. She was a well-known medical practitioner in Toronto, and extremely particular—she flew down to the resort in advance to inspect every guest room personally. She wanted Room A, but not Room B. Her family here, not there. The seating plan was an exercise in precision warfare.
As a company, we usually earn less than 10% commission on a destination wedding, and in this case, we absolutely undercharged.
Despite our pleas, she refused any rain contingency plans, insisting the weather would be perfect.
On the day of the wedding—during one of the driest times of the year in Mexico—the heavens opened. A freak tropical storm flooded her carefully chosen venue. Everything was soaked. We scrambled to salvage what we could, but it was clear: this was Mother Nature's mic drop.
The $50 savings that cost $12,600
One area couples don’t always consider is how we protect them from costly cancellation penalties. With our experience, we build buffer zones into every contract—setting internal deadlines that fall earlier than supplier cutoffs so we can cancel unpaid rooms without clients being hit with fees.
At one wedding, the bride’s father had remarried and was planning to attend with his new wife and their four children—six guests in total. As the final payment deadline loomed, we heard nothing. Emails went unanswered. Calls were ignored.
I reached out to the bride. “Is your dad coming?”
“Absolutely,” she said. “100%. Please don’t cancel.”
I explained that if they didn’t show, she’d be on the hook for 50% of six passengers' costs.
“I understand,” she replied. “If he doesn’t come, I’ll pay the penalty.”
We proceeded with the booking.
Later, we learned that he had quietly booked himself directly with WestJet, saving about $50.
Because he ghosted the original booking and didn't cancel in time, the bride was charged a $12,600 cancellation penalty. All to save a few bucks—and completely unaware of the contractual obligations his daughter had agreed to.
This is why working with an experienced destination wedding planner is critical. We know how and when to protect your bookings—and your bank account.
So why do people still choose destination weddings?
Despite the occasional chaos, destination weddings are often far more affordable and stress-free than traditional ones.
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A wedding at home can cost $40,000 or more. A destination wedding? Sometimes under $20,000—and in some cases, with complimentary rooms, room block credits, and kickbacks, they can even be free.
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They reduce guest lists naturally—it’s harder to justify 300 guests flying to Mexico, and couples often end up celebrating with only their closest circle.
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They turn into a holiday for everyone—your wedding becomes a week-long celebration with friends and family.
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And they’re simpler, with built-in services, trusted local vendors, and fewer moving parts.
After 1,500+ weddings, a few soaked setups, and a “white” horse that still haunts me, I can say this:
A destination wedding might not always go according to plan, but with the right planner, it will always be unforgettable.
Footnote: While I’m now semi-retired and rarely plan destination weddings personally, my experienced team is still hard at work. If you're dreaming of a wedding abroad, they’d be delighted to help make it a beautiful reality.
Ready for your next adventure? Join me in Tanzania this November for the Great Migration. Whether you’re travelling on your own , as a couple, a family or with a friend, this trip promises unforgettable experiences, incredible landscapes, and a welcoming group to share it all with. Details here.
Dont forget if you are looking to travel I still own a TICO registered travel agency in Ontario and will be happy to help. Always the best way to reach me is by email as I mostly work remote and I can either set up a time to meet you or suggest a perfect local agent to help you.
Email me at [email protected]
Email my Ontario Based Agents Michelle Lucy or Lauren Preston
Check some travel info at www.conciergetravelgroup.ca
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