Tim & Diann, Maui Wedding

Planning a Destination Wedding

Pacing and checking my phone had now become a constant habit. “Not one but two hurricanes headed toward Maui on the weekend of my wedding?” I asked in disbelief. It was an event planner’s nightmare – with 30 guests flying in from all over it seemed all would be lost.

A destination wedding can be an exciting way to take your friends and family to an exotic location with you. There are islands, castles, mountains, mansions and beaches available worldwide, ready to be part of an amazing experience. As every bride knows, you can plan all you want but sometimes a wildcard gets thrown in unexpectedly.

Our Wedding Experience
We had our wedding in Maui at our favorite resort on Kaanapali Beach. My husband had been going there for many years and the island had a family connection for myself as well. I started planning in January for a Labor Day weekend wedding.  I secured the venue, gave them a general understanding of the event and paid the deposit. I ordered the save the dates, invitations and the dress. A month later we booked the hotel rooms for ourselves and the guests, any plane reservations needed and then there was a long lull.

My dress, orchid lei and bridal bouquet.

Decor for the ceremony.


About six weeks before the wedding I started to get nervous – though I had done a lot of research and had a vision of what I wanted, the final details had not been set and emails were not quickly returned from the hotel wedding planner.  I contacted an external coordinator who moved things along. It’s a good idea to have you own coordinator. From there on out it was decision after decision – credit card authorization after credit card authorization, ad infinitum.

Trifold Invitations and Boarding Pass Save the Dates

Decor, Reception

Island half of the view from our room at the resort, Maui – before the storms.

Labor Day Weekend
There was tropical weather in Florida so we departed early for Maui to avoid any delays. The next morning we were having breakfast by the ocean, grateful to have gotten a few extra days to ourselves when one of my bridesmaids texted me to ask if I’d seen the weather report. I googled it and found something about a storm, but didn’t quite understand the potential impact. As the day progressed we got more information and realized there were not just one, but two hurricanes headed for Hawaii, set to hit within 2 days of each other – the first when guests would be arriving, the second in the middle of our weekend events.

As the realization hit about what would happen – we became progressively more upset. Though first trying to shrug it off as unlikely, as more time went by it seemed inevitable – sinister even – like a high tech weather smart bomb was being deployed on our wedding. We had both lived in Florida for many years, we knew what hurricane warnings meant. We had arrived in Maui almost a week early, looking forward to a mini-vacation which had turned into frantic research about forecasts, hastily-assembled back up plans and near constant worry that all would be lost. After waiting until midlife to get married, there was a profound feeling of unfairness to the situation. The radar even displayed a sad face of the two storms, as if the atmosphere had empathy and was saying: “I’m sorry.”

Actual radar image – a sad face for the Pacific Region with Hawaii to the left, not photoshopped.

Here we had done everything to attract guests and to encourage their participation, and at the last minute nature throws us a curve ball we didn’t plan for, and believe me, we’d planned for everything. Rain is a disaster at weddings, a hurricane can be considered catastrophic and two hurricanes is definitely off the charts. If I was more of a fatalist I would have taken it as a sign, but as someone who believes fate is interactive, I thought more about how we’d chosen to plan a major event during hurricane season, despite the fact that hurricanes rarely hit Hawaii. We were limited by my husband’s vacation schedule and we had normally experienced good weather in Hawaii in this time of year.

We went down to our favorite watering hole in Lahaina, hoping to dull the pain. We mentioned our situation to the bartender. He laughed and told us not to worry, that hurricanes rarely hit Hawaii – they usually hit the Big Island then veer off to the north or south. He said he had lived in Florida, so he understood our concerns, but added that the mountains there provide shelter.  We were thrilled, despite some skepticism. It was the first good news we’d gotten in days.

The next challenge was to convince people to come. Many of our guests were in the airline industry, so they were adventurous, seasoned travelers who knew how to plan for weather and what situations airplanes were capable of handling.  After the first storm started to veer south of the Big Island, we breathed a sigh of relief and got to work. He texted while I wrote a long message to our group about what we’d learned and what we planned to do about it. It was becoming clear that they could get to the island, I just wasn’t sure about all of our events. The ceremony had a backup location and the reception was indoors. I was mostly concerned about the cruise and luau, golf and brunch could be rescheduled. I found two other options, just in case.

Weather on Maui while the first hurricane was hitting the nearby Big Island.

I hit send and waited. In a few minutes I started hearing alerts, and was pleasantly surprised to see positive messages appearing from guests who were still planning to come. We ended up having no cancellations which was astounding, given that we were asking people to fly to the middle of the Pacific Ocean into two hurricanes.

As more time elapsed it was clear both storms would indeed veer around the island with minimal disruption. It felt positively miraculous, given the circumstances. Like hurricanes do, it sucked all the adjacent weather of pre-wedding jitters into the main storm anxiety, so after the threat was gone it was smooth sailing.

Pre-wedding Sunset Sail


Walking to Luau Feast

Luau Feast

Luau Feast

Due to weather forecasts, our sunset sail and luau were bundled together into one night and guests had a lot of fun and mai tai’s. The next day was open due to a little spritzing rain, but cleared as the day went on. Guests enjoyed the beach, pool, snorkeling and various day trips – each happy to get a chance to see the island rather than hunkering down in a hotel room as might have been the case.  Sunday was sunny, with some afternoon clouds that cleared for our 5 p.m ceremony.

For us the evening was a blur. Every moment was scheduled and we followed our coordinator’s lead throughout. There were funny moments of my heels getting stuck in the grass while walking down the aisle, happy memories of island music in the sun during cocktail hour, an incredible sunset photo session of the bride and groom on the beach, and a warm, happy reception that lasted for hours but seemed like it was over far too soon.

Sunset at our resort

Now that the bills have been paid and the weekend went off without a hitch, we are glad we planned a fun filled weekend for all. We got to travel with friends we would never get to travel with as a group, to introduce some people to a new part of the planet, and to share a long awaited special day with our near and dearest.

Just Maui’d

Whole group

Cocktail Hour Duo

First Dance


Head Table Decor

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