Oahu, Hawaii: our perfect beach holiday destination, complete with a sunset proposal

Oh, how the heart wanders for faraway, distant shores…

Yet another peaceful, perfect sunset in Waikiki.

Picture perfect sunsets, private horse rides on the beach, lei and luau, fine dining, and exploring among the coral reefs makes a trip (or several) to Hawaii a must

I’ll never forget our trip to Hawaii. For so many reasons, it truly captures the heart.

The journey: no pain, no gain

It’s always a real challenge for my family to see each other. We’re so spread out… almost as if we couldn’t get far away enough from each other when we all started moving after college. From New York, my brother Ed and his family moved out to the West Coast, to California; my mom on the East Coast, moved south, to North Carolina; and me, I moved even further east, to London. The distances are staggering – which usually makes for seeing everyone in person a once-in-a-year event.

So when it was summer of 2018, and Christmas planning came up, my brother’s family suggested we all meet up in Hawaii.

Hawaii… for Christmas? It sounded so exotic. Christmas for us usually meant the snow, the cold, roast dinners, and decorated fir trees.

It was always one of those destinations that I’d always vaguely dreamed of going to, at some point in my life – but never really had a chance to because of the sheer distance.

But with this suggestion, there was no better excuse to go.

Alex and I were excited. We love travel (who doesn’t?) – but we’re quite different on how we approach travelling. She’s particularly good at travel. Me, I’m probably a bit too much on the lackadaisical side. If the trips were left up to me (which they usually aren’t), we’d probably never get to do the great attractions that you should do as a tourist – all the things that involve pre-planning, pre-booking, queueing.

Family get togethers… means A LOT of miles

Usually, I’m more of a “land and see what happens” kind of traveller, and I’m usually not bothered to miss out on something because I didn’t book. There’s no regrets, if you didn’t look into it right? I could easily just find myself in a nice restaurant or bar and just enjoy the world around me.

Ed and his wife’s family chose Waikiki beach, on Oahu. Probably the most famous, and most touristy? destinations in Hawaii.

Definitely well worth the visit because it’s so famous, and it’s known for its very surfable, family-friendly coral shores.

From what we could see, it wasn’t our usual style. Alex and I prefer quieter, off the beaten track, places – and while we do the touristy thing, we tend to mix that with more of the private experiences. So this trip was going to be a bit of a change for us.

But because we figured the primary reason for us going was to be with family, we thought we’d not make many plans and just be available for dinners and the like. We’d just drift around the family hotel where we were going to be staying and see what happened.

The only thing we did plan however was a private horseback ride. We’re both avid horse riding lovers – Alex grew up with horses around, and since she’s introduced it to me, I definitely love it. Turns out there is a place on the north shore of Oahu that catered to private sunset rides. It sounded perfect.

Hawaii is made up of 8 major islands but actually has approximately 137 total.

Getting engaged: the plan starts to hatch

It must have been a week or two after we started booking that I’d realised I was going to propose.

Alex and I had been together for probably 6 years by this point – and suddenly I’d realised that a trip to Hawaii, with what I’m picturing in my head – seemed like the perfect place.

The horseback ride – private, on the beach, the sunset – when the thought popped into my head, it was almost as if I had wished I’d thought of it sooner, and I started thinking about what needed to be done.

The very first thing – being traditional in this sense – was ask for her parents’ blessing. This turned out to be far more difficult than I’d imagined.

First, logistically – finding time alone with her dad: because they live outside of London, we’d go see her parents over a weekend or so and Alex and I would naturally travel together. So, finding time alone was going to be difficult. Luckily the perfect opportunity did present itself; her dad had just recently purchased a new two seater, and when the family all decided to go into town to get coffee one day, I suggested he show me his new toy, just the two of us.

Second, having the chat itself was probably one of the hardest conversations I’d ever had to build up the courage to do. I work in pretty stressful, conflict-full environments, with tough business negotiations – but these paled in comparison to this chat.

Anyway, long story short – I took the challenge and asked her dad to pull over, and in a car park, had an amazing conversation with the man. Mission accomplished.

Next, it was ring shopping, all done over a matter of months of learning, choosing, and selecting. I even had her parents come down to London on the day of choosing between three rings, to get their input – and we ended up with this beautiful stone and classic Tiffany solitaire setting.

Taken the day she got it. To this day, the shine can take my breath away.

The ring is important when describing this trip, because for the next 6 weeks or so, it would be burning a secret hole in my pocket, causing me constant fear and panic of losing it, and being something I had to keep hidden from the person who was with me most of my time.

I did not enjoy my traveling with such a pricey object on my possession.

Something I’m sure most men in this situation can relate to. Let me tell you – I was constantly thinking about it. It caused me no end of stress. I imagined problems at every turn. Even going through the airport was going to be potentially an issue. I just pictured going through security and having to empty out my bags, and having the ring discovered then.

Luckily I had a few work flights before we left for Hawaii, and I’d asked airport security. They seemed to suggest that it wouldn’t be something that they’d ask to take out of the bag – but they didn’t seem sure. There are however some excellent tips on google – so, fellas, for reassurance:

  1. keep the ring in the jewel box, but not the outer gift box, and the bow – allow for easy, quick access if needed
  2. put a note on the jewel box, in large lettering – “engagement ring – please be discrete”
  3. tuck away in something your future partner won’t go through or see but someplace that allows for easy for access if security needs to go through it

The ring was in my laptop bag front pocket where I thought Alex would least likely need to get into, and I would have my laptop bag on my person at all times.

I could just imagine, getting pulled aside and having to go through the bag in question with security. You can imagine that, right? Traveling with someone – they’re usually stood right there with you as security goes through your things.

So this little internet tip did give me a bit more peace of mind; but all for nought, as I passed through security without incident.

But it still wasn’t over. Even when I arrived in Hawaii, at our hotel – I was constantly worried. What about housekeeping? I can’t put it in the safe – that’s where we put the passports and joint things, and she’ll be able to get to it there. I’ve read that you can ask the main desk to use their safe, but that’s also a risk because you’ll need to get separate from her, and I’ve also read some anecdotal horror stories of things getting lost from the front desk. I chose to keep the ring in my laptop bag, in the closet, next to the safe, where she would likely leave it alone – and just had to trust that the hotel staff wasn’t going to rifle through my things.

But I was worried. We landed on a Monday night – and riding was on Wednesday evening. I just had to make it through til then.


We flew from London to San Francisco, which took 12 hours. Then a 5 hour layover. Then another 5 hour flight, and we’d be in Hawaii. The time zone difference was 11 hours.

Alex cooked up a plan so we could get back on the right sleep schedule straight away: we were going to stay awake, and not sleep on the flights, and when we got to Hawaii, we’d arrive around 9pm in the evening and we could go straight to sleep then.

It was brutal.

I’m actually used to missing sleep – working in investment banking has made me more impervious to pulling late, or all nighters. It sucks, for sure, but I know what it feels like to miss a night of sleep.

But somebody was in for a real treat.

By the time we got to the 5 hour layover, she was definitely lagging. And on our 5 hour connecting flight from SF to Honolulu, she wasn’t going to make it.

I kept prodding Alex, reminding her it was her plan, to stay awake. She literally burst out in tears, she wanted to sleep so badly.

She wouldn’t make for a very good interrogation subject, or navy seal, I thought to myself. Here I am holding her head during the flight as she zonked out.

One of us stayed awake. And one of us has a heavy head

Waikiki Beach

Waikiki beach on Oahu island – lots of hotels and gentle surf

We ended up staying in the resort that the rest of the family booked – this hotel called the Alohilani Resort in Wakiki right on the beach.

Not that that’s actually saying much – because practically all of the beachfront for a very long stretch is made up of hotels. It’s a very built up resort area. To be honest, my first impression of Waikiki beach was feeling a bit disappointed, because it felt more like a city, and in my head I had conjured up some stereotypical relaxing beach images. (More on that later – there are definitely places like that on the island.)

Not an endorsement. if you’re interested –

But I can say that this place was a very easy stay. Again, Alex and I tend to go for private rentals mostly – usually a nice AirBnb, but I could see the appeal of this airy resort.

if you’ve got family, this place is very easy, relaxing, and modern with all the comforts. It’s perfectly placed to host families with children, with lots of activities throughout the day for everyone. It definitely was comfortable and right on the beach, and with my 5 year old nephew around, we definitely needed a place that catered for this. So all in all, we really enjoyed our stay here. It felt classy, and well run, and they put up a giant Christmas tree in the lobby – which was a nice touch.

Riding on the beach

It was Wednesday, and Alex and I were ready for our private horseback ride. At sunset. We rented a car, relatively painlessly, and drove to the north shore of Oahu.

The north shore is entirely different to Waikiki. It’s exactly what I imagined in my own head.

Rushing, thrilling waves – depending on the time of year, the waves are so high that they’re off limits to swim in, but spectacular to watch from the shore. It’s quieter, and a lot less touristy. You start to see more luxurious private homes – especially the waterfront. We stopped off at several places along the way just to take it all in.

We’d chosen Hawaii Polo Oceanfront Trail Rides for our private ride – and it will to this day be one of my most cherished memories. It could not have been more picturesque and perfect.

Gentle breezes, soft waves, wildlife. We saw the sea turtles in the surf on our majestic horses.

The horses at Hawaii Polo Oceanfront Trailrides are polo horses that are used when not on season – which means riding some very professional, responsive beauties.

My beauty, Bella – she’s one of the larger ones and loves a cheeky nip for snacks

Our guide and us makes three

After the ride, we walked back down to the beach, and it was literally just the two of us for as far as the eye could see. We sat on the shores and soaked in the rays of the setting sun.

Right before I proposed

Mai tais back at the hotel that night

It went perfectly.

Safe at last, on her finger, and no longer my concern – it’s all her problem now!

Food and sights

So much Japanese food…

We didn’t realise how strong the connection with Japanese culture and cuisine was, but it was everywhere. A lot of Japanese tourists, apparently, and lots of Japanese restaurants. It makes sense, now that we thought about the connection with WWII and Pearl Harbor – but we didn’t know the extent of it when we arrived.

We ate Japanese food for most meals. Sushi, udon, ramen, katsu, and more katsu. Actually, some of the best katsu I’ve ever had.

But while we love Japanese food – we were dying for some variety mid-week. We ended up chasing some Americana – short ribs, coconut shrimp, pasta – to break up the palette.

Thursday, we spent the day in Hanauma bay, which isn’t far from Waikiki, and it’s another highlight of the trip. It’s a protected coral reef where you can hire snorkels and fins, and just observe the wildlife. There are points in the bay where you can spot the sea turtle colonies – though we didn’t manage to see them on our visit. It’s a very wide bay – but for a long way out, it’s quite shallow due to the reef.

Protected coral reef at Hanauma bay

On Friday, we ended up going with the family to a luau – which is basically a ticketed event in the evening – it’s a bit OTT, fun for the kids, buffet event with roast pork and trimmings. It’s a bit of history of the Polynesian islands, mixed in with fun song and dance.

Again, very easy fun if you’ve got kids. We went to the “Ka Moana” (“the ocean”) luau at Waimanalo beach – just a short distance from Waikiki and easily shuttled to.

Alex looking a little lost when invited on stage to do the “hula

Surfing lessons are a big must do. I can see why Waikiki is known for its surfing – not only are there loads of places where you can go and rent a board, but it’s just really easy surfing in Waikiki. The waves are mostly calm, and consistent, and for the most part – the beach is sandy and safe. There are sharp coral reefs on this side of the island as well, but in distinct areas.

We booked a lesson and took to it immediately – though we don’t have any pictures to show for it, I stood up first go.

My nephew on a surf lesson, Waikiki beach. So much water activity – the kid was almost always in the surf or in the pool


It was an amazing trip – and especially memorable for us because we got engaged doing one of the most picturesque things I could imagine.

I’d highly recommend this trip to anyone looking for an easy, no pain, family oriented destination, with lots of family activities – lei making, luau , coral reef swimming, surfing lessons, and more.

Yes, the variety of restaurant cuisines is somewhat lacking, and it feels very touristy feel in certain areas, but there is so much more to explore that makes up Hawaii – my only regret is not having made the trip longer so I could have explored the neighbouring islands.

I’ll definitely be back again to make that happen.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: