Ashleigh and Christie

Maui and Oahu, Hawaii   |   View Registry


“I’ve never actually swam in the open ocean before,” Christie casually mentioned as the catamaran pulled away from the dock and I watched our chance to get off the boat quite literally float away.

I peered at her over my sunglasses and asked, “Are you serious? Why did you agree to this snorkeling excursion? They are truly dropping us right into the ocean.”

“Because I knew you wanted to do it,” she answered shyly and I couldn’t help the smile that took over my face.


I’ve known about Christie’s love-hate relationship with water since the beginning; she’s more of a spectator than a participant. I’ll never forget the time I forced her to follow me into the intimidating wave pool at Disney’s Typhoon Lagoon water park under the guise that the waves would merely lap at her ankles. But as I watched a giant wave pull her under and spit her back out, I knew she would never willingly follow me into the water again.

But yet, there we were, cruising the crystal waves off the coast of Maui and our destination was much more intimidating than a theme park’s wave pool. The seas were choppy and the sun was barely shining, but Christie still played along like a trooper. Yes, we wanted the optional wetsuit; yes, we would gladly accept the flotation device made for children—anything to make the experience less terrifying for her.

The boat stopped—in the middle of the ocean, as promised—and the crew dropped the anchor. After a brief snorkeling lesson, they set us free. With all of our equipment in place, we made the slow descent into the water. Sure, there were tropical fish surrounding me and a whole ocean to explore, but I was focused on Christie who definitely didn’t share my excitement. She gave it a fair shot for about five minutes, long enough to say she did it, but then she hit her max.

“Really, I’m fine,” she promised as her flipper-clad-feet propelled her back into the boat. And with the promise of unlimited beer, wine, POG juice, and Maui potato chips onboard, I truly knew she would be. She watched and waved from the deck, snapping photos of me as I glided along the surface, amazed at all the life that existed mere inches from my fingertips.



Maui was everything we needed it to be for the start of our honeymoon. We left Boston, Massachusetts on the morning of July 16, 2018, literal hours after our wedding. And if you know a thing or two about geography, you’ll know Boston is not a hop, skip, and a jump away from Hawaii. We spent the majority of the day traveling and when we arrived at the Sheraton Maui exhausted from the wedding and jet lagged, we could immediately tell it was going to be the perfect place to recharge.

The relaxed vibe of the hotel immediately flipped a switch for us. We were out of wedding planning mode, out of wedding party mode, and transported straight into relaxation mode. Our ocean view room that overlooked the property’s immaculate grounds and massive pool was like a dream. I never imagined we would be lucky enough to stay in such luxury, but it was honestly due in part to Wanderable that we could.

Christie and I were together for seven years before we got married, and we lived together for the majority of that time too, so we didn’t need any of the typical bridal shower or wedding gifts. We already had pots and pans; we already had linens and glassware. But do you know what we didn’t have? Enough money to snorkel, island hop, enjoy a gorgeous sunset dinner cruise, or eat our hearts out at fancy luaus. We went to Hawaii because we knew we could round out our dream honeymoon with those extra experiences we couldn’t afford on our own.

And Maui was honestly the best place to start that adventure. The hotel staff delivered drinks to us while we floated in the pool; we slow-danced under the moonlight to a ukulele player at a luau; we ate purple ube pancakes for breakfast; we snorkeled (well, I snorkeled) with brightly-colored fish; we watched the most insanely vibrant sunset either of us had ever seen from the deck of a boat after dinner. The island was calm and welcoming and delivered the perfect dose of relaxation to start off our happily ever after.


Onto Oahu

After a quick flight (seriously, it was about thirty minutes long), and staring down at picturesque views of mountains and cliffs, we were magically on another island. Oahu was, in many ways, the opposite of Maui. We stayed at the Hilton Hawaiian Village on Waikiki Beach, which is right in the heart of Honolulu. The resort itself was its own little town, so we felt nice and set off from the city itself, but right outside the gates, the place was bustling. I couldn’t believe we could see skyscrapers as we laid out on the beach.

The hotel itself offered an overwhelming amount of activities and we knew from the get go that we wouldn’t be able to do them all, but we certainly tried. Our first night in Oahu consisted of drinks and dinner overlooking the ocean and a spectacular fireworks show on the beach at the hotel. What better welcoming could we have asked for?

And from there on out, it was just one incredible experience after the next. Every morning we woke up with two difficult decisions to make: which pool we should start at and what toppings we wanted on our açaí bowls. We made our own leis, got henna tattoos, went paddle boarding and kayaking in the hotel’s massive lagoon (there were no fish or open waters this time, so Christie was much more willing), and rode the waves all with Diamond Head as our breathtaking backdrop.

Unlike Maui, everything was within walking distance from our hotel in Oahu. We could walk to dinner or to shops or get drinks if we wanted, although the resort did offer quite a selection to begin with. We strolled down the streets of Honolulu hand in hand one night and stumbled upon a section that included hundreds of local vendors selling their homemade wares. And even though it wasn’t a planned, perfectly-thought-out activity, it was one of the most memorable experiences for us both.


Use It, Don’t Abuse It

Our friends and family encouraged us to tell everyone we spoke to on our adventure that we were on our honeymoon because “you never know what you might get.” Our feelings on the matter were less enthusiastic because we knew our honeymoon destination wasn’t the most original, obviously. But that doesn’t mean we never brought it up.

We waited for the opportunity to present itself organically, and we were certainly rewarded when we did. After hours of trying to find ourselves a rental car the morning of our planned day trip around Oahu (bad planning on my part, I’ll admit), we were ready to throw in the towel.

“Just one more place,” I pleaded with Christie as we walked into the hotel next to our own. It took us longer than I care to admit to find the rental car desk, but when we finally did, it was worth all the stress of the morning.


Yes, they had a car available (miraculously) and yes, we could have it right away. The man at the desk looked at my license and noticed we were from Massachusetts—his home state as we quickly learned. And when he asked if we were there celebrating my birthday which was only two weeks before our wedding, I saw my in.

“No, we’re actually on our honeymoon,” I said and his face lit up. He made a few phone calls, asked us if we were okay with the sun on our faces while driving, and Christie and I could immediately see where this interaction was heading.


“I have a Mustang Convertible available if you want that,” he said like it was nothing. Of course we were interested, but we were concerned about the price. I truly think I had to pick my jaw up off the floor when he told us he would rent it to us for $50 total, only if that was okay, he asked. We assured him we could swing it.

An hour later, we were in the coolest car either of us had ever driven. I’ll be the first to admit that we’re not really car people, but we at least knew this one was fancy. What we didn’t know, though, was how to turn it on. We were too embarrassed to admit defeat to the rental car lot staff, so ten minutes, a few YouTube videos later, and bruised egos, the car came to life. Turns out I wasn’t holding down the button long enough—like I said, we’re not car people.

With the top down and a perfect day ahead of us, we took our time driving across the island, making stops at the Dole Plantation and then ending at Disney’s Aulani Resort for dinner and a spectacular view. It was a spontaneous and go-with-the-flow kind of day, something we would never do back home, and it was perfect.


The Logistics

Between some crafty pooling of hotel points and the immense help of Wanderable’s easy-to-use site that we made uniquely ours, we ended up spending about $3,000 total for ten days of luxury in Hawaiian paradise. It all came together rather easily after I did enough research, both from guidebooks and online. I chose the majority of our excursions, luaus, and hotels based on reviews I read, and also from firsthand recommendations from people I knew who had been recently.

The thousands of pictures I took definitely don’t do the islands justice, but there are a few shots I’m proud of on Instagram (ashleigh_osgood) that convey the true happiness we felt every second of our adventure. The people were so kind and welcoming; the natural beauty was breathtaking; and the romantic atmosphere of the islands in general made for a perfect destination to start our married life together. We would both go back in a heartbeat.