I Booked a Flight and an Airbnb for My Honeymoon and Left the Rest Up to Chance

Why would we choose this moment to stress out over a trip when the entire point is to relax, enjoy each other’s company and discover exciting things together?
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Why would we choose this moment to stress out over a trip when the entire point is to relax, enjoy each other’s company and discover exciting things together?

“Maybe we can plan a honeymoon when our schedules ease up. We’d have a little more time to save,” I said to my soon-to-be husband, feeling a little defeated. This was just a few months before we got married, and I’d been researching options for a Hawaiian honeymoon on Oahu. Think of the pristine beaches, stunning views — what better way to welcome life as young married folks and take our first real vacation together? To be honest, we both really needed this vacation, especially since we’d spent a ton of time living apart — hours, even time zones apart — devoting most of our waking hours to our careers.

As you can probably imagine, things were looking pricy. Okay, really pricy. Dream-crushingly pricy, especially for two people who’d just invested a good amount of hard-earned cash in our wedding. Could we suck it up and pay up for a few big-ticket honeymoon-themed specials? Sure. Did we want to carry that burden (and did it financially make sense)? Not really. In fact, not at all. The Hawaiian honeymoon landscape was an unaffordable promise land of exorbitant plush suites, rose petals, and hand towels shaped into strange-looking animals.

Did we make our dream honeymoon happen anyway? Heck yeah we did! 

Our experience was made possible by opting to book the cheapest flights we could to Honolulu, reserve an Airbnb, and plan nothing else.

We did this for two reasons: first we were stressed out by the idea of an inevitably expensive itinerary (even if we had tried to create one, we likely would have been unable to make it happen financially). Second, when it really came down to it, we just needed to unwind. We were both feeling burned out, and we’d never put this much pressure on ourselves to plan a long weekend with friends. Why would we choose this moment to stress out over a trip when the entire point is to relax, enjoy each other’s company and discover exciting things together?

To sum things up, making the decisions to go plan-free until we arrived made our honeymoon better than I ever could have imagined: no honeymoon-themed “specials” or suites required. Here’s a recap of what we gained from making no plans (and a few tips on how we kept things cost-effective). In ditching an itinerary, we really gained everything. Booking an Airbnb instead of a hotel made us feel like we lived there (and it was really awesome).

Tourist destinations like Waikiki are considered classic honeymoon vacation spots, but we opted for quieter Lanikai, where we stayed in a room of our Airbnb host’s home. We looked into this option because it was far cheaper than booking a honeymoon package — cheaper by half, even (not kidding) — and because we felt we’d have a little more freedom. We couldn’t have made a better choice. Since we’d rented from a local of 40 years, we had the benefit of a built-in expert vs. a cookie-cutter concierge. She was able to share so much about the wonderful things we could do in her neighborhood on a flexible schedule! 

I’d also recommend, if you like to cook or even assemble sandwiches, that you book a place with a communal kitchen. We ended up buying groceries to make all of our own breakfasts and lunches (sometimes dinner too), pocketing a ton of money that would have been blown elsewhere. It meant we got to eat casually at what felt like our kitchen table, rather than making an event out of every meal out of necessity.

Pro tip for when you do venture out for a special dinner: Don’t be afraid to make it known that you’re on your honeymoon. We quickly learned that this new badge of marital privilege comes with a lot of free dessert on the house.

By leaving our days open, we were actually able to relax. When we got to Hawaii, we quickly found our morning routine: hang out the patio and go for a walk to the local beach in the afternoon. Our host had organized an idyllic outdoor space with chairs and tables overlooking Lanikai, so we were able to relax and soak in the views in a secluded environment (we pretty much had the pool to ourselves, which we wouldn’t have elsewhere). Following that day, and for every day after, we’d pour some coffee, make some breakfast and talk about what we could do that day. No commitments. Then, after we’d lounged for a good hour or two, usually in a hammock or sitting by the pool or overlook, we’d usually decide on something together (and no, it wasn’t expensive jet ski rentals or parasailing for two). Our host had stacks of local maps and guides that we checked out to get the inside scoop on the prettiest local beaches and best hiking spots. 

We also took advantage of the six-hour time difference from New York to Hawaii — it meant we were wide-awake at 4 a.m. Since we didn’t try to force the time change right away to gear up for activities, we had the freedom to wake up naturally and see stunning sunrises. We were even rewarded with humpback whale sightings off Lanikai Beach one morning!

We had great local experiences we wouldn’t have had otherwise (and most of them were free). After browsing our host’s guides, we ended up doing some really spectacular stuff. It’s an excellent spot for people that love to hike like we do. We climbed the Makapu'u Point Lighthouse Trail, took a scenic drive on Highway 83 along the coast and stopped at shave ice spots and delicious shrimp trucks along the way — we even ended up finding a great hike in our own backyard. As it turns out, our Airbnb was backed up against Lanikai’s famous Pillboxes Hike, so our host let us know where to find the opening of the trail. There, we were able to explore two abandoned military bunkers and see stunning water, beach and mountain views. 

Makapu'u Point Lighthouse

Makapu'u Point Lighthouse

During our one afternoon adventure to touristy Waikiki, we met a lovely couple that was celebrating their 30th wedding anniversary (and their first vacation without the kids in two decades). Since we had free time, we spent hours chatting, and they ended up very generously inviting us to dinner — something that never would have happened had we planned out our trip to a tee.

Overall, were there things that we didn’t get to that we would have loved to do? Sure. But we did absolutely live in the moment. Believe it or not, we chilled so hard that we left Hawaii without going snorkeling. Making no plans helped us take a step back and focus on enjoying each other, and adventuring together, rather than spending our energy, precious time and too much money running around to have someone else’s idea of a perfect experience.