You type “getaway” into google. What you really want is a sense of freedom, escape from ritual … mixed with a curiosity to try something new. Destination weddings are a cycle of these feelings: a thirst for loafing with cocktails by the pool, spiked by an urge to hop on a boat and snorkel.

                     The Bride arrives to her ceremony via canoe over translucent green Hawaiian waters.

Ryan and Cassie embraced this mix. They let their guests enjoy the freedom of their own choices while still providing options. They also were smart enough to balance group time with private time: hanging poolside with their crew, sneaking off for an hour-long deep-tissue massage, followed by a Valentine’s dinner at the incredible Merriman’s restaurant in Waimea. That alone time refreshed the mind for the incredible fun with the group.

The masterstroke: a boat expedition (via Ali’i Tours) for whale watching, swimming with dolphins, and snorkeling in Kealakekua Bay. With a small core of people committed, they sent the mass invitation and let the rest come and go as they pleased. See the teaser video below! 

Hi Life – Teaser from IZ Cinema on Vimeo.

At this point, I had so much footage, and everyone had already had so much fun that they could have wed on the bow of the boat and it would have seemed right. Having the experiences leading up to the wedding was such a great feeling, like a really good warm up stretch before a run. There were no hard turns or abrupt points of entry like in traditional 1-day wedding events. We came, we saw, we played, and by the second day we all felt like we were strongly grounded in why these two people should be married. This was a truly unique destination Hawaiian wedding.

Wedding day was nearly the opposite of the fast-paced days that preceded it and so strange (in a good way) for someone like myself who is so used to high-pressure environments. While I had my Hawaii-appropriate short-sleeved collared shirt ready for the event, I had spent enough time mingling with the group by then that I knew I could show up in flip flops and shorts for the early part of the preparations. Besides, if I can’t say “I showed up to work a wedding in flip flops and shorts” in Hawaii, when will I ever?

Preparations and 1st look were ridiculously mellow, setting the tone for no-stress as we headed to their ceremony/ reception site: The Napua Restaurant at Mauna Lani. Their site was a beautifully simple patch of grass with a solitary tree centerpiece nestled in a private beach cove. The tree was adorned with lei strings, but other than that they let the beauty of the surroundings speak for itself. No crazy arrangements, placards, or anything to distract from the stunning beauty of what they had all come to see. There was one novel twist: Cassie’s father had arranged an outrigger canoe to paddle her to the shore where she would walk down the aisle … make no mistake, this was not a sure thing if there were choppy waters, but fortunately all was calm on the ocean that day.

Once they had committed, what was their key to doing it right? If I had to boil the list down it would look something like this:

– Have everyone there at least 2 days before the wedding
– Have a residence that is designated party and another that is designated peaceful
– Pre-plan at least 1 big group activity with a core group, but don’t stress on how many come
– Preplan at least 1 private dinner for you and fiancé
– Keep your ceremony arrangements/ garnishes to a manageable few

But what if you haven’t committed yet? What if you’re still daydreaming and unsure if you can handle it? Well, the last section below is for you.

Is it right for you?

Sometimes the dream of doing something is infinitely better than the reality of if you doing it. Depends on the person. Depends on the experience. For example, my dream of getting crazy dramatic shots of people slack-lining across a desert plateau is so much cooler in my head than what would happen if I had to actually capture it; I’m terrified of heights and while it might make for a great Insta post, most of my memories of the experience would be white-knuckle stress about not plummeting to my death. For others, no problem. Is your destination idea purely a vanity daydream? Or is it something that you and whomever you invite can pull off without going crazy?

Most people think of destinations as vacations, so the cocktail analogy might work well here.  There are some liquors that go down like water and others that just don’t agree with us. Knowing what’s in the cocktail ahead of time can help us decide if we’re going to order that drink. Here are the 4 basic parts:

1-Your Personality

Know yourself. Once the daydreaming subsides, can you really allow yourself to be at peace with not having control of arrivals and departures. Who does what and all of those details? Clearly, you should have a friend / planner delegated for this but once that’s done you still have to be willing to be relatively hands off.

2- Expectations

Your expectations should also dictate this: if you’re expecting people to go explore in groups and share in the experience, you should have options on hand, have at least one solid group who can commit and let the rest follow where they may or may not. If you’re expecting people to just hang and relax, that will determine your accommodation recommendations.

3- Your Crew

While this can obviously get tricky, in general there is a simple majority rule test that can help here: are the majority of people you’d invite able to be self motivated, helpful, and willing to take part in whatever your vision of the experience will be? I know, it sounds so simple, but it needs to be asked honestly.

Parents are the only joker in this deck. If you have an overactive parent, you have to honestly ask yourself if he/she will likely be running around like a maniac trying to tell people what to do. If so, the next question is can you/ siblings manage that so the parent is somewhat satisfied, or at minimum shielded from stressing out the rest of the party / vendors?

4- Your Location(s)

The answers to #1-3 should inform how challenging of a location you’re willing to pick. And by this I’m not suggesting you have to have a certain personality type … again … it’s all about the mix: You can be mellow or high-energy and as long as your crew and expectations are in harmony, then even a wedding on a rock pillar in Meteora, Greece followed by a reception in Santorini is possible. Obviously, the larger size party you have, the shorter distance between wedding and reception should be planned … ideally in the same location.

So wether you’re daydreaming of your own destination wedding, or looking for ideas for your friend’s destination Hawaii wedding, remember that this cocktail is so much more than just the location.