I struggle with the same dilemma every single time I book a hotel. It’s a throwback to a stint in my twenties spent surviving on smuggled hostel breakfasts stretched to cover lunch, and FlixBuses timed to cross entire European borders overnight so I wouldn’t have to pay for a bed.
So even now – older, arguably wiser, and considerably better equipped to appreciate the value of a resort with an infinity pool where the odds of bedbugs are slim to none – something inexplicable comes over me every time I sit down to make a five-star reservation.
Despite now having the means to afford a place with expensive toiletries, I still can’t quite make peace with the fact that my holiday will no longer resemble the iconic itineraries of my backpacking era: a time when I would visit 43 churches, 16 Zaras and 68 museums in a single 24-hour period, before retreating to whatever “it’s just somewhere to sleep for the night” airbnb I’d booked for 16 euros.
A recent trip to Hawaii took that choice entirely out of my hands.
After securing an excellently-priced spot at Prince Hotel Waikiki via Luxury Escapes, I duly formulated an itinerary where I attempted to replicate the fail-safe template of my twenties. One that would allow me to (re)visit Pearl Harbor, Diamond Head, and the Polynesian Cultural Center by day, then return to the hotel by 7pm to swap denim shorts for designer heels and head out for the night. Sleep and then and repeat for the next five days. I’d roped in my best friend Ros for this one — a trip where we’d planned the itinerary over voice notes for weeks beforehand, and where the hotel needed to work for two females with very different definitions of ‘a good holiday’ under one roof.
Plot twist: Tropical Cyclone Lala, which made landfall on the second day of our five-day stay, had other plans. It hit the islands. Hard. Genuinely, seriously scary – flooding roads on the Big Island, cutting power to well over 100,000 homes across the state, and, tragically, claiming a life.
It is not a storm I’d wish on anyone, and the scale of what it did to communities elsewhere in Hawaii is not something I want to gloss over in service of a good anecdote. But, on Oahu, where I was staying, it also – in the strange, narrow way that disasters sometimes do – effectively trapped me inside one of Waikiki’s better hotels for 64 hours. And in that specific, fortunate corner of the story, I’d happily do it again.
The Other Harbour
Most people who fly into Honolulu go looking for one harbour in particular. Pearl Harbour gets the tour buses, the audio guides, the solemn queues. But, check into Prince Waikiki, and you’ll find yourself gazing out at an entirely different one: the Ala Wai Boat Harbour, Hawaii’s largest yacht marina, a forest of masts bobbing gently against a Diamond Head backdrop. It’s the harbour nobody tells you about, and – storm notwithstanding – it turned out to be worth the trip on its own.
The placement of Prince Waikiki on the edge of this port is genuinely clever – a location on the quieter, western edge of Waikiki, means you get proximity to the main strip’s shopping, nightlife and beach without actually being swallowed by it. Kalakaua Avenue’s chaos is a manageable stroll away, while the enormous Ala Moana Center, one of the largest open-air malls in the world, is closer still.
It’s the sweet spot between “in the thick of it” and “able to hear yourself think.” It’s also an easy hotel to explore on foot, day or night – useful when two friends inevitably want different things from an evening and neither wants to be talked into an Uber she didn’t ask for.
The hotel itself carries more history than its glassy, resort-modern exterior lets on. It’s named for Prince Jonah Kuhio Kalaniana’ole, a Hawaiian royal born into the line of the Kingdom of Hawaii, who later served for nearly two decades as the islands’ delegate to the U.S. Congress and remains one of the most revered figures in modern Hawaiian history – genuinely royal, in other words, not just marketing-department royal.
The current building underwent a $55.4 million top-to-toe renovation in 2016–17, which is the reason nothing about the place feels dated: think a lobby anchored by a suspended sculpture of hundreds of hammered-copper fish, locally commissioned artwork throughout, and interiors that lean coastal-contemporary rather than lei-and-tiki.
Rooms are the other headline act. Every single one faces the ocean – floor-to-ceiling glass, no exceptions – and ours, on the 30th-something floor, delivered on arrival exactly what Luxury Escapes’ Instagram promised: a wraparound view over the marina, Diamond Head hazy in the distance, sailboats slipping in and out of the harbour below.
It is, on a clear day, one of the better hotel views I’ve had in Hawaii, full stop. Also worth noting for anyone booking as a pair: the rooms are genuinely spacious enough for two adults to actually live in for five days without it turning into a rom-com montage of tripping over each other’s suitcases.
It was a rather different view from the emergency stairwell. When the storm hit and the power went out, ‘spacious room on a high floor’ briefly became ‘extremely long walk down a pitch-black stairwell in the dark,’ which is not a sentence I ever expected to write about a five-star hotel, and not an experience I’d recommend seeking out.
Credit where due, though: the exit signage was clear, the stairwell held, and staff stationed themselves at intervals to check on guests as we went. Having a friend beside me the whole way down helped more than I expected – someone to trade nervous jokes with while your phone torch fights a losing battle against thirty flights of pitch black. Character-building, if nothing else.
Day One: The Infinity Pool, While It Lasted
Before Lala had so much as entered the group chat, Ros and I had one full, gloriously ordinary day at Prince Waikiki, and we used it exactly as intended: horizontal, by the pool. The hotel’s infinity-edge pool is the kind that photographs better than you’d expect and swims even better than that. It sits right at the harbour’s edge, so the illusion is that the pool simply dissolves into the marina and, beyond it, the ocean. Loungers, a pool bar, the whole production. It is precisely the sort of amenity my twenty-something self would have scoffed at. But, one my current self would happily never leave. Two loungers pushed together, a shared plate of something fried, and absolutely no obligation to make conversation with anyone but each other – this was peak best-friend-holiday territory.
In hindsight, I’m very glad we didn’t put it off till day two.
The Club Lounge: A Retreat, Whatever the Weather
Club Lounge access is one of those hotel perks my budget-backing era could never justify. However, 45-year old Marie-Antoinette was left wondering why I waited so long. On a sunny day, it’s simply a lovely spot to retreat to – quieter than the pool deck, better views than the lobby, and a steady rotation of snacks and drinks that make it very easy to justify an afternoon spent doing nothing at all.
On a cyclonic day, it turns out to be something closer to a lifeline. Once the storm properly set in and the hotel lost power, the Club Lounge became the de facto command centre for a small, slightly bedraggled band of guests looking for somewhere to sit that wasn’t a darkened room.
There are, it’s worth saying, considerably worse places to be marooned than a lounge with drinks on tap and a steady supply of food, even generator-powered and slightly improvised. I will not be complaining about complimentary canapes while outside actual buildings were losing their roofs elsewhere on the island. Ros and I ended up playing three consecutive rounds of Connect Four with a couple from Alabama we’d never have met otherwise – the type of small, unplanned bonding a girls’ trip occasionally throws up when the itinerary falls apart.
100 Sails: The Buffet That Held the Line
The hotel’s signature restaurant, 100 Sails, occupies the second floor with the same harbour views as the rooms above, and its seafood-heavy buffet – generous with the crab legs and proper Americana desserts classics like Key Lime Pie – is the sort of spread you plan a day around rather than squeeze in. On my first, storm-free night, it delivered exactly that: an excellent, unhurried dinner with a sunset over the marina thrown in for free.
What I hadn’t accounted for was how well it would hold up once the power went. A hotel restaurant losing electricity mid-cyclone is a genuine operational nightmare. And yet 100 Sails kept functioning – a scaled-back menu, understandably, but hot food, cold drinks, and a room that stayed calm even as the windows rattled. Buffet loyalty earned, under considerably more pressure than intended.
The Staff: Who Rose to an Occasion Nobody Asked For
I’d wager the staff at Prince Waikiki are excellent under any circumstances. But it’s one thing to be warm and attentive when the biggest crisis of the day is a slow room-service order, and quite another to keep that same energy when your hotel has just lost all power mid-storm and a lobby full of anxious guests are looking to you for reassurance.
They did it anyway.
Seemingly out of nowhere, staff produced board games in the foyer, with the calm efficiency of people who’d clearly trained for exactly this kind of chaos. The on-site cafe kept the coffee coming, free of charge, for anyone who wandered past looking like they needed it – which, by hour thirty of a stopped elevator, was most of us. Nobody I encountered seemed anything less than genuinely glad to help, which is a much harder thing to fake than a nice lobby.
Stormy Stay. Five Star Rating
I went to Hawaii expecting Pearl Harbour, Diamond Head, and a lot of quick outfit changes. What I got instead was 64 hours largely confined to one very well-run hotel, and – with real, serious damage happening to real communities elsewhere on these islands, which deserves far more attention than a hotel review can give it – I feel genuinely lucky that my version of “trapped by a cyclone” amounted to board games, an excellent buffet, and a harbour view.
The Prince Waikiki didn’t just weather the storm. It made a five-star case for the argument that a hotel’s true test isn’t the infinity pool on a sunny day, but what happens when the lights go out.
It also passed the toughest test of any girls’ trip hotel: my best friend and I emerged from five days of sharing a room still speaking to each other, which is more than most hotels can claim credit for.
Consider this one a five-star review, cyclone and all.