Most of our trips begin with a place we want to see. Our May 2025 journey through Asia began with a hotel.
When Milaidhoo Maldives became bookable through Hilton Honors following the Small Luxury Hotels of the World partnership, I found a redemption that was hard to ignore. Three nights in an overwater villa for 390,000 Hilton points, with half-board meals and seaplane transfers included in our reservation at the time. It was the sort of opportunity that made me rearrange the trip around it.
So that is exactly what I did. Korea, Taiwan and Singapore became part of a much bigger journey whose original anchor was a tiny island in the Maldives.
The unusual thing is that I am not much of a beach-holiday person. After three nights at Milaidhoo, I still wasn't. But I wouldn't trade the experience for anything.
Why we went back to the Maldives
We had visited the Maldives before, staying on a local island rather than at a private luxury resort. That trip gave us warm hospitality and a perspective on the country that would have been difficult to find inside a resort. This time, we wanted to experience its other side: an overwater villa, a private pool, the ocean beyond the deck, and the feeling of being able to stop moving for a few days.
For someone who normally likes visiting several places in one trip, committing three nights to a single small island was an unusual choice. But the booking gave us an opportunity to experience something I had admired for years and would never have been comfortable paying the usual cash price for.
There was a practical puzzle to solve, too. I couldn't find a useful direct routing to the Maldives for our dates. Seoul became a natural first stop because we both wanted to visit South Korea. A modest addition to an Aeroplan itinerary made a Taipei stopover possible. Singapore then worked as our route towards the Maldives, while also giving me a chance to revisit college friends and my partner a chance to see Singapore for the first time.
The trip looked complex on paper. In my mind, it was simple: make the journey worthwhile, not just the final hotel.
The flight that made the destination feel real
The seaplane transfer was my first truly unforgettable Milaidhoo moment. Once we were in the air, the Maldives looked almost unreal: turquoise water, scattered islands and narrow ribbons of sand surrounded by an enormous expanse of blue.
It was also less comfortable than the photographs might suggest. The aircraft was cramped, and the cabin became stuffy. The flight felt longer than I would have liked, particularly after the journey we had already made to get there.
I would still do it again for that first arrival. There is a difference between seeing aerial photographs of the Maldives and watching the islands appear beneath you as you approach your own.
Walking into our overwater villa
I have stayed at some memorable hotels, but walking into our villa at Milaidhoo is a moment I expect to remember for a very long time.
There was the ocean, right outside. There was our private pool. And there was the realization that this wasn't a photograph or a future aspiration anymore. We were actually spending the next three nights in an overwater villa in the Maldives.
Milaidhoo was as luxurious as we had hoped. But what stayed with me wasn't a long inventory of amenities. It was the sheer contrast with everyday life: stepping outside and having the ocean rather than a street or skyline in front of us.
For all the complicated planning that led here, the most rewarding part of the stay was remarkably uncomplicated.
Dream Lux Travels
Dream Lux TravelsThree nights with almost nothing planned
We didn't book excursions. We didn't plan a diving trip. We didn't try to fill our days with activities simply because we were in a destination that people travel enormous distances to see.
Instead, we relaxed, spent time in our private pool and enjoyed the island. Milaidhoo is small enough that getting around isn't difficult; the resort had golf carts available, but we didn't find them necessary.
This was an intentional change of pace. I am usually happiest moving through cities, finding neighbourhoods, restaurants and unexpected stops. On an island resort, the experience comes to you rather than the other way around. For three days, I was happy to let that happen.
The vegetarian food was another pleasant part of our stay. We enjoyed our meals, and breakfast in particular offered enough variety that it became something to look forward to. The resort's dining was genuinely good, not merely 'good for a remote island.'
There was, however, one disappointment. We had a special multi-course beach dinner that we enjoyed, but we had not been clearly told in advance that it would incur an additional charge beyond our meal plan. The issue wasn't that a luxury resort charged for an optional experience. It was the lack of clarity. When you are somewhere as expensive as Milaidhoo, knowing exactly what is and isn't included matters.
Dream Lux TravelsWhat the points actually changed
Our May 13-16, 2025 booking cost 390,000 Hilton Honors points for three nights. The reservation included half-board meals and seaplane transfers at the time, which made a significant difference to what the stay would cost us overall.
Those inclusions were central to the decision. It would be a mistake to assume they come with every Milaidhoo points booking now, or that the same award price will be available again. Seaplane transfers, dining and extras can change the economics of a Maldives holiday dramatically.
But the larger value, for us, was not a spreadsheet calculation. Without the points, we probably wouldn't have booked this kind of stay at all. They allowed us to say yes to an experience that would otherwise have remained a beautiful idea.
Would we go back?
Probably not anytime soon, and I don't mean that as criticism of Milaidhoo.
We are city travellers at heart. We love being near the water, but we don't dive, and I have spent enough of my life around beaches that I don't feel the same urge to return to them repeatedly. The distance from Vancouver adds another reason to prioritise somewhere new.
Three nights were exactly right for us. I wouldn't shorten the stay, but I also wouldn't have wanted to extend it. We got the ocean, the villa, the food and the rare luxury of doing very little. That was the point.
I would make the same booking decision again if I could go back to May 2025. I just wouldn't mistake a wonderful one-time experience for a destination I need to keep revisiting.
Some trips change the way you travel. Others fulfil a dream so completely that you can move on, satisfied. Milaidhoo was the second kind, and I'm very glad it was.
Dream Lux Travels