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Backstory - I'm a US expat and travel hacker living in Sydney with my wife. We've been here for 6 months and seen a lot of the same questions about the area get posted almost daily. I'll do my best to concisely run through a number of topics here, whether it be about getting here or what to do, in the hopes this makes future questions a little more tactical.
NOTE: PLEASE PROVIDE FEEDBACK IF YOU WANT TO CONTRIBUTE!
Update 1 - Added booking windows and intra-region travel info.
Great deals to be had lately in economy. Prices have consistently dropped $800 or so from mainland USA on full service carriers. These sales are pretty frequent. If you have Chase Sapphire Reserve card a $800 cash ticket is just over 53,000 Ultimate Rewards points with FULL points earn on the ticket itself. That's a great deal if you don't care about sitting up front. Business class is significantly more expensive. This is one of the most sought after premium class routes on the planet and with that prices tend to stay high and award availability low.
From the East Coast of the US
I highly recommend AA to DFW and Qantas DFW-SYD. The route is served by a comfortable A380 (good economy, dated 2-2-2 J though) and loads are typically intentionally kept low heading East to maximize cargo capacity. That means you can realistically expect a empty middle seat if you plan well. On the eastbound side it's still possible but less likely. Also, if you fly on low days you may score an upgrade for $1,000 - $1,200 USD per person, per way, via Qantas' bid for upgrade program. Really the major benefit here is connections going further into the US - minimizing travel time on either side of that long leg is incredibly more valuable and comfortable.
From the West Coast of the US
Any carrier works here, chose based on your preference. Every domestic carrier serves the route (UA/AA/DL) and most are newer aircraft (sans Delta's aging 777s). You can also find good deals via Fiji as well as via Auckland on Air New Zealand. I personally don't like breaking up the trip any more than necessary so I don't like those options.
Oh boy, this is a good one. Generally the rule of thumb is simply this, PLAN AHEAD IF YOU WANT TO FLY UP FRONT! The only exception to this is Virgin Australia who sometimes releases J space < 2 weeks of travel. That's absolutely rolling the dice though. Economy wise you can typically find space on at least one carrier so that's less of a topic, and as above, with cash prices being so low it can often be less worthwhile to book the award itself. Up front you really have a few options. US Carriers
Good J hard product, meh soft product. Awards open up here and there but typically it's very limited to last minute redemption. Price-wise, they're not the cheapest, but not the most expensive.
probably the best hard produce from the group. Same meh soft product (they're US carriers after all). Pricing is also okay, but availability is next to none.
bad products, hard and soft. The seats are old, the service is older. Price is highest BUT you will often find saver-level seats on Virgin Australia (a partner) < 2 weeks out.
meh J product (2-2-2). Good/Great F. Service is also good, very polished. Availability in spurts, but okay price via AA.
best seat (the Business) and I'm a sucker for a bird with a bar. Conversely, terrible availability unless you're looking within 2 weeks or right at the window.
Asian Carriers (generally better availability)
my personal favorite. Great airline, great US service, and a transfer partner of Chase. And most importantly, they tend to be quite generous with their availability.
old favorite in the points world. Not the cheapest option but if you have the points then you'll often find availability through HKG when you book at the window. Great seat, classic service, and AMAZING lounges in HKG.
like ANA, in light of recently US carrier devaluations these guys have become a viable option through Tokyo. Some recommend their 777 SkySuite as the best J product out there.
Suites are always a favorite but lately it's pretty impossible to not pull your hair out before actually confirming that route. J availability tends to show up here and there. Recently devauled though so use tool to find best option based on points available.
mentioned in JAL topic, just a solid all around option if you have the points.
Award Tools Look, I know a lot of carriers were mentioned above and you're probably going well, that's all great, but how do I ultimately choose one given the fact that I have a trip 1+ year out and a few options? That's where the below sites come in handy. They will tell decipher award charts and help you distill down the airlines that you can realistically fly given the points that you have.
Staying in the South/South East (SYD/BNE/MEL/PEetc.) - Avios, Avios, Avios! SYD-MEL, for example, is 4,500 Avios one way on Qantas. This is an amazing sweet spot.
Cross Country Travel - This is tough. Economy prices aren't terribly high, but the business class product on these flights is top notch. Virgin flies "The Business" A330 and Qantas flies an equivalent A330 through the continent and they really cater to those premium travelers. I still haven't come up with the best way of doing this with points though local frequent flyers swear by the points upgrade to get up front.
Across the Ditch (To/From NZ) - My recommendation is Air New Zealand. I recently booked this and spent 25k Krisflyer (Singapore) for a RT flight on Air New Zealand. I definitely consider that tremendous value, though discount carriers operate these routes and you can find deals (I would consider $300 round trip in economy to be a good deal).
Rule of thumb, if you have 5+ days in the region than I suggest going outside of Sydney. It's a cool city, but there is SO much more to see. Scroll down for details, but while in Sydney here are a few suggestions:
Taronga Zoo – One of my favourites. A great place to see all the local animals that the US doesn’t have. This is a FANTASTIC first day activity and will help you fight jet lag!
Bondi to Cogee Walk – A beautiful self-guided walk down the coast. It’s just a walking path but it's a must do.
Harbour Bridge Climb – Climb atop Sydney’s most famous bridge to see the city like nowhere else. Younger people love it, older people tend to avoid it. I haven't done it and don't plan to.
Sydney Opera House – The most famous landmark in Sydney. We could see a show or just do a tour. Up to you.
Manly Ferry/Beach – Manly beach is amazing and the surrounding area is filled with bars and restaurants. This would take up the majority of a day. The ferry there and back is a mini sightseeing tour in and of itself.
Sydney Bus Tours - Highly recommended as it takes you all over the city and even out to Bondi. Hop on/Hop off style so you can wander if you like a stop.
Sydney Boat Tours – Just like the bus tours, the boat tours allow you to get off at stops and explore. A great way to maneuver around the water and hit the main points of interest. Could be a good way to see Manly, too. Do NOT do a dinner cruise, the food is bad and it's just a waste of time.
The Rocks – Located right in the harbour, the Rocks is an area with numerous restaurants, a famous market and Australia’s oldest pubs.
Darling Harbour – Like the Rocks, DH is another touristy area on the water that has a ton of restaurants and bars. Also has a Ferris wheel, an enormous fish market with tons of fresh seafood, and a casino.
Sydney Seaplanes – Name says it all. I absolutely LOVED the "Sydney Secrets" tour.
Featherdale Wildlife Park – Never been here but it comes highly recommended. Basically it is an animal park where all of the animals are loose and you can interact with them. All of the Australian animals will be there. It is a little bit of a drive but definitely doable.
Blue Mountains – A national park that has a bunch of beautiful views and is much different from the water you get all around the city. They have a similar bus tour to all the attractions which lets you hop on/off at will. A train will take us directly up there if you’d like to go.
Hunter Valley – Australia is known for its wine and HV is the closest region to the city.
Places to Stay
Park Hyatt Syndey - go to place for best of the best stays. On Cirqular Quay with views of Opera House.
Westin Sydney - downtown, good location (10 min walk from quay), nice hotel.
Hilton Sydney - downtown, same as Westin.
Intercontinental Double Bay - ritzy area of town, looks to be a nice hotel. I live nearby so I'm biased - it's a good spot but out of the hustle and bustle.
Marriott - also downtown, 5 min from quay. Lobby recently redone, rooms are supposedly very nice, too.
Four Points Sydney - closer to Chinatown but still downtown. 20 min qay to quay. I've heard it's nice.
There are tons more, this is a whole topic in an of itself.
Are you outdoorsy?
Queenstown, NZ (~3 hour flight) - The end all be all go-to place for being outdoors. If you like being outside/hiking/etc. this should absolutely be on your list See extreme activities section.
Blue Mountains - see above.
Royal National Park (~30 min from Sydney) - great national park with some beautiful hiking spots. Not huge, but easy to get to and is a good excursion.
Do you like food/drinks?
Melbourne (pronounced Melbun) - Where to begin? Really the best way of thinking about Sydney vs. Melbourne, which is a HUGE rivalry by the way, is to put it simply as > Sydney has the sights whereas Melbourne has the culture.
Cairnes (pronounced Cans) - the gateway to the Great Barrier Reef. Backpacker town (if you want a nicer area near the GBR see Port Douglas) and full of bars and nightlife. If you're younger, want to hang out with some peers, and go diving, go here.
Queenstown - the extreme sports capital of the world or something like that. Has it all - skiing, skydiving, bungee jumping, rafting, etc.
Featherdale Wildlife Park - Near Sydney, see above section.
Taronga Zoo - see Sydney section.
Austrlaia Zoo - Up near Sunshine Coast, not familiar with it.
Melbourne - see food.
Uluru - Where Ayers Rock is. Great for the "Outback" experience. Can fly (3 hrs) from Sydney, not/nothing else there though.
Lord Howe Island - limited access island. Super exclusive. Best value is booking out and using Qantas points to get there. 16k or so round trip for $1,000 flight.
Hamilton Island - right off barrier reef's southern end. Beautiful islands with Whitsundays islands nearby.
Port Douglas - the nicer way to get to the Great Barrier Reef (as opposed to touristy/backpacker Cairns).
Bondi/Bronte/Coogee/etc. - Eastern beaches. All near Syndey. Bondi to Coogee walk will show you most of them.
Northern Beaches (30 - 45 min car ride from city). More laid back beaches outside of the city. Slower paces, friendlier locals.
Assumes 10 days down under.
Day 1 - Land in SYD, drop bags at hotel, change, and head straight to Zoo. DO NOT NAP. Try to stay awake until 7p or so. Good luck.
Day 2 Sydney - Hop on/Hop off bus tour. Do Bondi to Coogee walk when you get to Bondi. Figure out what you like and don't like along the way.
Day 3 Travel to Melbourne - Dinner downtown.
Day 4 Melbourne - Coffee, walk around CBD, Great Ocean Road maybe?
Day 5 Travel to Queenstown, NZ
Day 6 Queenstown - Outside
Day 7 Queenstown - Outside
Day 8 Travel to Sydney
Day 9 Sydney - Opera House tour. Ferry to Manly for lunch/afternoon.
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