Yes, I know you’re pissed at us for saying we like Melbourne better. But let us make it up to you. You have your own attributes.
But the cruise ships that dock in your harbor daily? Unfortunate.
Let’s not dwell on it.
If it’s your first time in Sydney, do not go directly to the harbor, which holds the Opera House and the Harbour Bridge. We recommend instead walking through some of the neighborhoods, from Chippendale to Surry Hills to Paddington, then circle around to Potts Point and Woolloomooloo (one of the most fun local words to say, next to “marsupial”), come through the Royal Botanic Gardens, and sneak up on the Opera House. This does two things: First, it allows you to get a non-tourist experience by seeing the parts of the city where people actually live. And it gives a different perspective of the harbor and the widely photographed Opera House. You can modify the route to go from Paddington to Woolloomooloo to the Gardens if you don’t want to walk as far.
To absolutely no one’s surprise, the Sydney Harbor is touristy. Especially at night, when the mediocre restaurants are overcrowded, the aforementioned cruise ships pack the docks until about 7:00, and the Opera Bar is jam-packed.
There are many to choose from, in many different neighborhoods. Thankfully, Uber is ever-present in the city, because it is pretty vast.
The Rocks is tourist hell, the oldest neighborhood in the city, right next to the cruise ship docks, and virtually under the bridge. It’s filled with bars and restaurants. If you’re here, the most quality stops are The Doss House (a fairly new whisky bar in a great location and space) or Grain Bar (yes, another whisky bar) for drinks, and the Pony for lunch or dinner.
The CBD (Central Business District), just south of the Rocks, has a few great cocktail-bar finds. Restaurants first: Restaurant Hubert is regarded as one of the better restaurants in the city, with good reason. For cocktails, there are a few world-famous cocktail bars (again, with good reason), first and foremost, the Baxter Inn. The Baxter Inn is one of those places in a location designed to make first-timers feel like idiots, in a courtyard just off the street. You’re greeted by two other bars in the courtyard. Although neither of these is your destination, stop at the Barber Shop first to make it look like you’re not searching—they make a mean gin and tonic. Then enter the unmarked door on the opposite corner from the Barber Shop and go downstairs.
See, you’re a local already.
The Chippendale and Redfern neighborhoods became our favorite places in the city because they felt more real, young, and vibrant, with lots of great restaurants. And not touristy (in case you haven’t figured it out yet, we’re into “not touristy”). Spice Alley is a collection of Asian and SE Asian places gathered in an outdoor food hall (similar to the LA Farmers Market) with seating and order counters. Remarkably, it seems all of the restaurants in this little spot are pretty good, run by people who know the cuisine.
Automata, across from Spice Alley is often named as one of the best restaurants in the city, and is a great spot. We preferred lunch because of the more tasting-menu format at dinner. Two other notable restaurants in this area are Ester, which was our overall favorite in the city, and LP’s Quality Meats, if you’re in a carnivorous mood.
There’s a comfortable little eclectic neighborhood bar in Redfern (the new up-and-coming spot), Moyas Juniper Lounge. Maybe not a destination, but worth a stop in you’re in the ’hood.
In Surry Hills, Darlinghurst, and Paddington, there are a few places worth a stop. Nomad in Surry Hills is worth a dinner or lunch sitting at the chef’s counter to watch the culinary theater. For drinks (Sydney loves its cocktail bars), try Eau de Vie in Darlinghurst. In Paddington, you’ve got wine bar 10 William Street. For a more crowd-pleaser space and menu, there is also The Paddington (owned by the same group as Bulletin Place).
What Not to Miss:
Ironically, both of our must-dos are touristy—so the fact that we’re recommending them says a lot. Dinner at Bennelong, in the Opera House, where they offer an a la carte Cured and Cultured menu sitting at a chef’s counter overlooking the harbor and the city. The food is first-rate, and we sat next to Sydney residents who have decided it’s worthy. It’s a great chance to see the architecture first-hand.
Where to Stay:
The Park Hyatt is the best-known, best location, and probably highest-priced. But you do get incredible vistas of the city, the harbor, and the cruise ships as they pull into port at 5:00 a.m. (If you hadn’t noticed, we’re not big fans of cruise ships.) If you walk in front of the hotel along the water, you also get a great perspective of the bridge from below. If you’re in Sydney for multiple days, this location is worth a night, but probably not your whole stay because of the touristy location. The Pier One, an Autograph Collection property, is a short distance from the Park Hyatt, a bit more off the beaten path under the bridge. It doesn’t have the same views, but it boasts a quieter location in the Rocks. The Shangri La and Four Seasons are also in the Rocks and Harbor area and give great views, but for the money, the Park Hyatt is better.
We also loved the Old Clare in Chippendale. Great neighborhood and location, and a converted brewery in a well-designed, unique space. Our room was the old board room of the brewery and was uniquely preserved, down to the crazy corner urinal formerly part of the men’s bathrooms. It was one of the more creative rooms we’ve seen. Also, Chelsey at the front desk left quite an impression. She actually looked us up pre-visit and sent a custom note referencing our “everyday champagne,” and helped us find some of the places above.
Do not stay at the Establishment, unless you’re 22 and looking for a scene. It’s a boutique hotel that looks good online, but it’s all about the bar and the nightlife.
Our first day in Sydney was during Melbourne Cup. Think Kentucky Derby, but a weeklong and country-wide phenomenon of dressing up and drinking (it was as if fascinators had thrown up on every woman’s head). Everything was closed except for bars and restaurants on the biggest race day.
So buck up, Sydney. You’re pretty good, too. You’re just more of a tourist mecca that it took awhile to make peace with, and your restaurants are typically not open all day. (In Melbourne, they open at 11:30 and stay open. Not that we’re comparing or anything.)
But you were a great stop both before and after Tasmania. And, yes, the Opera House does make for a good picture—and an even better meal at Bennelong.