Both hotels are skyscraper city hotels and both share the same amenities; pool, executive lounge and multiple restaurants. I have a Hilton Diamond card and that should provide early check in, room upgrade, guaranteed lounge access, breakfast, fast wi-fi, free access to the pool/gym and late check out. Rather than write two separate reviews, I thought I’d combine them and see which hotel won.

Early check in and room upgrade: We arrived at both hotels around 10:30 in the morning after early-morning flights – I didn’t expect to check in that early at either.
Hilton Sydney: The lady at the desk was really friendly and helpful, but advised that it would be a few hours before we could check in. An upgrade was confirmed. She sent us, without me asking, to wait in the Executive Lounge as they were just finishing the breakfast offering. We spent a few hours in the lounge and our room was ready by 13:00.
Hilton Osaka: The man at the desk was really friendly and helpful, but advised that there wasn’t a room ready for us – especially as he wanted to upgrade us to an executuve room. I asked about waiting in the lounge and he was happy to call them and advise that we would be waiting there. Breakfast had finished but they kindly found us some pastries and made tea and coffee. Our room was ready by 11:30.
The winner of the early check in and room upgrade challenge?: Osaka with 5/5 and Sydney 4/5.

The room:
Hilton Sydney: The room was excellent with spectacular views over Sydney. There was a separate bath and shower, king-size bed, bathrobes, slippers, large flat screen TV with various Australian channels plus international news – the only small thing missing was the complimentary bottles of water, although the tap water was fine to drink.
Here is the view from the room:

Hilton Osaka: The room was excellent, especially large for Japan, with spectacular views over Osaka from a panoramic window. There was a ‘wet room’ with a separate bath and shower, king-size bed, bathrobes, slippers, pyjamas, large flat screen TV (only CNN and BBC news in English), a Nespresso machine and kettle, plus two complimentary bottles of water each day, although the tap water was fine to drink.
Here are some pictures of the room plus the view:






The winner of the room challenge?: Very close but the room size (for Japan) and panoramic windows mean that the prize has to go to Osaka with 5/5 and Sydney 4.5/5.

Wi-Fi: Both hotels provided a ‘fast’ wi-fi access code and both codes were remembered by the devices when we wanted to connect – no annoying re-entering of the code each time. The wi-fi in Sydney was fast, Osaka slow, although I could see it was fast in the middle of the night. I guess there are a lot of people connecting in Osaka, but the hotel should cater for that.
The winner of the wi-fi challenge?: Sydney with 5/5 and Osaka 3/5.

Hilton Sydney: The lounge was large with spectacular views of Sydney from three sides. The staff were relaxed and friendly. The evening ‘happy hour’ from 18:00 to 20:00 (where alcoholic drinks and snacks are free) was the best I’ve experienced from a Hilton lounge; plenty of food available, unusually enough that you could skip dinner and dine in the lounge and a bar service with a good array of drinks available.
Hilton Osaka: A small lounge with great views of Osaka, albeit from only one side. The staff were formal but friendly. The evening happy hour was 18:00 to 20:30 but the size of lounge meant that it was often full and guests had to return to their rooms and wait for a call when there was space – something I’ve never encountered before. The snacks were very small ‘amuse bouche’ type – as soon as they appeared there was a stampede and they were immediately gone. Drinks were served at your table with a good array of drinks available.
Both lounges offered breakfast and afternoon tea. We always used the main restaurant for breakfast. Afternoon tea was good for both, although I preferred Sydney as they had scones, jam and cream – but that’s just a regional variation.
The winner of the lounge challenge?: Sydney by a mile 5/5. The small lounge and limited food is a real issue for the Hilton Osaka with 2/5

Hilton Sydney: I visited the pool to ask what the protocol was for visiting – as this was a city hotel, I wanted to know if guests travelled from their rooms in their bathrobe and slippers. The attendant said “You can just wear a swimsuit in the elevator if you like – nobody will mind!”. The pool was in a windowless room and was pretty chilly. There was a jacuzzi and four sauna rooms, each with a different environment; dry, steam etc.
Hilton Osaka: The hotel rules state that you mustn’t leave the room in bathrobe and slippers (except, I guess in the case of a fire). I wore my swimming shorts, trainers and a t-shirt to the pool and had some strange looks from both staff and Japanese guests who believe that only schoolboys wear shorts! On arrival you must change your shoes for slippers, then proceed to the locker room to change – I just went straight through and found a box containing swimming hats plus a notice that they must be worn. The pool area had a large frosted window to the outside. The pool was just the right temperature. There was a jacuzzi and apparently a sauna, but I didn’t try to visit as I was sure there were numerous rules associated with that.
The winner of the pool challenge?: Sydney with 4/5 – the relaxed nature of the hotel meant that I’d be happy to visit again, whereas in Osaka (3/5) it was just too much hassle and I also didn’t like wearing that stupid hat.

Hilton Sydney: The breakfast restaurant felt sophisticated, staff were really friendly, especially those originally from The Netherlands and there was a good view to the Queen Victoria Building across the street. The choice of breakfast items was excellent. The only downside was that anything other than a regular coffee, such as cappuccino, was chargeable AU$5.
Hilton Osaka: The breakfast restaurant was quite basic, staff provided good service typical of Japan, there wasn’t much of a view. The choice of breakfast items was excellent, although missing Western-style sausages, but benefitting from delicious Dim Sum and Miso soup. Cappuccino was included and available.
The winner of the breakfast challenge?: Sydney with 4.5/5, but only just as the charge for premium coffee almost lost them the vote. Osaka 4/5

Late Checkout:
Hilton Sydney: I called and asked for a late checkout as we weren’t flying until 10pm. They could only offer 2pm. I asked about paying for extra hours and the most they could offer was 4pm for AU$100 – which we took.
Hilton Osaka: On check in we were given a list of benefits, including late checkout to 3pm. I visited the front desk and asked for a late checkout and it was clear that I could have pushed for 4pm – as it was we only needed 2pm.
The winner of the late checkout challenge?: Osaka with 5/5 and Sydney 2/5

The Overall Winner?

Osaka Sydney
Early Check in and Room upgrade 5 4
Room 5 4.5
Wi-fi 2 5
Lounge 2 5
Pool 3 4
Breakfast 4 4.5
Late checkout 5 2
26 29

Hilton Sydney with 29 points!