We loved Sydney. After sailing there for the holidays, it was hard to leave. What started as a month long visit became a wonderful two month stay. I miss the city’s clean streets, happy residents, busy bars and restaurants, excellent museums, and fun festivals. The best of Sydney ranges from cool music venues to funky neighborhoods to free art galleries and beautiful hikes.
Best Anchorage: Glebe Bay
My list of the best of Sydney wouldn’t be complete without talking about where we spent most of our time on the boat. Sydney has a lot of great anchorages, and it’s easy to move around as long as you avoid the ferries. You can anchor somewhere for great beaches and elsewhere for the fireworks. For us, the most convenient bay for shops and sightseeing was Glebe, which has three anchorages.
Glebe, Blackwattle and Rozelle were great anchorages for the selection of safe and convenient dinghy docks. We had dinghy parking at the fish market, the ferry dock, or Rozelle Bay park, giving us access to multiple shops, restaurants, and transit lines.

The Blackwattle and Rozelle Bays were also a favorite because despite their proximity to the city, they were calm and quiet. Boat traffic is pretty light, and the main noise from shore was dogs and cicadas. The only annoyance was the early Sunday morning dragon boaters and their megaphone using guides.
Favorite Neighborhood: Newtown
We took the bus to Newtown many times over our two months in Sydney. Newtown has great breweries, live music venues, and a huge variety of restaurants. It’s a place where all ages meet to mingle and have fun.

Best of Sydney: Live Music and Theatre
Undoubtedly, we have spent a lot of time in some very remote places, with limited choices for culture. Sydney is like a breath of fresh air, with tons of options for music and theatre.
Sydney is such a cultural city that we could have heard good quality live music every night if we chose. It was nice to “live” in a city again and enjoy all the entertainment on offer.
In our time in Sydney, we saw free outdoor performances, went to music clubs, and took in a concert at the Sydney Opera House. We grooved to live jazz in parks and rocked out to Jack White at the Enmore.

We took advantage of the live music and the theatre. Finally, after years, we got to see Hamilton on stage, and it was everything it’s hyped up to be.
Food and Drink

From too many pubs to count to seafood markets and Chinatowns, food is fresh and plentiful in Australia’s biggest city. One of our best experiences was a Japanese meal at a sake bar in Newtown. We tried Indonesian, Chinese, Spanish, Turkish, Indian, BBQ and more. The population of 5.5 million is diverse, so everyone’s cuisine is represented.

High Art and Street Art
In between riding buses and light rail, we also walked the city. The different neighborhoods are fun to stroll, admiring cool architecture, both old and modern, and lots of street art.

Funky neighborhoods with cool street are Marickville and Newtown in the west, and Surry Hills in the inner-east.


We visited world class art galleries in the city. Top picks include the free to enter Art Gallery of New South Wales and the Asian only White Rabbit Gallery.

The Great Outdoors
What a great city to be outside, especially in summer! We spent a lot of time walking through beautiful parks and gardens, all so close to the vibrant streets.

We walked a lot in Sydney, crossing over bridges for beautiful city views to explore different parts of town.

Of course, we hiked the popular seaside trails. And we spent some hot days at Sydney’s amazing beaches, full of surfers and swimmers all summer long.
Festivals
Summer is festival season, and we enjoyed many! We enjoyed music and art during Sydney Festival, attended a beer and comedy fest, and even a fireworks festival. What a great city to spend your summer!

The Geocaching Community
On one of our first nights in Sydney we went to a geocaching meetup. It was at a brewery and full of fun and friendly local geocachers. It was great! We made friendships that continued in our time in Sydney and beyond, and found a lot of caches.

The Blue Mountains
If you have time for a day trip from Sydney, The Blue Mountains are beautiful. We were lucky to be led by some local friends, and even though we didn’t have the best weather, we did get to hike a little and see the iconic Three Sisters.

Another day trip – or overnight if you have the time – I highly recommend is visiting The Hunter Valley, one of Australia’s top wine regions. It offers great food and wine plus outdoor attractions.
There is so much to love about Sydney. I hope you have a better idea of what you want to do when you visit. Let me know in the comments what you love about this Australian city, or what you would enjoy!



