After celebrating New Year’s Eve with a night of fireworks and bubbly in Sydney, Lindsay, Katz and I were only slightly hungover and excited to be making our first visit to Melbourne. While I had always thought of Melbourne as Australia’s clear second city, its population is just short of Sydney’s (both cities hover around five million people, representing about 40% of Australia’s total population).

I had heard great things about Melbourne’s gritty vibe and laneway art (also known as street art), as well as its vibrant food & beverage scene. It is also a short day trip to both the Yarra Valley and Mornington Peninsula wine regions. Needless to say, it would be no dry January for the three of us.

Day One: Easing into the New Year

Even though our 90 minute flight from Sydney to Melbourne wasn’t until 2pm on the 1st of January, we were unsurprisingly quite tired on the first day of the year. Nevertheless, we planned to check out a few bars and have a casual dinner out before calling it an early night and getting a good night’s sleep at our Airbnb in Melbourne’s CBD.

After checking into our sunny and modern condo (which came at a significantly more affordable price than our dark and dated Sydney Airbnb, I should add), we decided to head to the nearby Fitzroy neighborhood for some dinner and drinks. Quick side note: while traveling in Japan the prior April, I had met a fellow American named Harry, who had just wrapped up several years of living in Melbourne. We kept in touch over social media and he shared his extensive lists of recommendations for both Melbourne and Tasmania, which I drew upon heavily during this trip. Unfortunately, many of the bars and restaurants in Melbourne were closed on New Years Day, including most on Harry’s list. We ultimately found a bustling rooftop bar and wrapped our evening up at a casual yet delicious Thai restaurant. Sadly, I don’t remember the names of either of these venues.

Enjoying some rooftop rosé, when Lindsay was delighted to learn that our Uber driver had located her lost sunglasses and could drop them off at the Park Hyatt in Sydney for me to later retrieve

Back at our Airbnb, we were impressed to see the EDM show across the street still going strong. Those people had WAY more energy than we did on the first day of the year. Fortunately, the concert ended at 10pm, at which point we were all tucked into bed, with the lights off.

View of Melbourne and the EDM show from our Airbnb (sorry I can’t figure out how to center the video properly!)

Day Two: Walking Tour, Queen Vic’s Market, Picnic, Fitzroy Bar Crawl

After an amazing night of sleep, we felt like brand new people on the 2nd of January. It was time to get 2020 properly started.

First up: Exploring the city in the morning on a tour led by I’m Free Walking Tours. While in the past I had looked down on guided tours, particularly free walking tours, the previous year of travel had served to open my mind a bit. I had experienced some incredible tours that had exposed me to much more than I would have seen on my own (I particularly enjoyed the free walking tour in Kyoto led by a younger, gay, Aussie Ashton Kutcher doppelganger). Since we only had a few days in Melbourne, we all agreed that a walking tour would be a quick and easy way to absorb a history lesson, navigate the city, and perhaps even extract some additional recommendations.

Turns out we weren’t the only ones with the same idea. We showed up at the meeting point at the State Library of Victoria and found it swarmed with tourists from all over the world. Thankfully, ‘I’m Free Walking Tours’ was not only adept at finding a name to simply describe their product– they also knew to have plenty of enthusiastic tour guides on hand to service eager customers during peak tourist season.

We were assigned to a group of about 20 people and started on our way. Along the route: the Old Melbourne Gaol (spelled “jail” in the U.S.), laneway art, Carlton Gardens, Federation Square, and much more.

View of the Yarra River, Princes Bridge and CBD. We were very lucky to have a clear, sunny day in Melbourne as fires raged all through Australia

All in all, it was a worthwhile few hours to acquaint ourselves with the city and learn more about Melbourne’s heritage. But not quite Ashton Kutcher lookalike level– guess you have to go to Japan to find those Aussies?!

Next on the agenda: hopping on the tram to Queen Victoria’s Market (or Queen Vic’s Market for short) to pick up wine and snacks, then to Carlton Gardens for a lazy afternoon picnic in the shade. While the park wasn’t overly crowded, we delighted in watching the groups of people around us practicing yoga, playing music, and reading.

Our final plan for the day: returning to the main drag in Fitzroy for an early evening bar crawl. While a number of bars still remained closed for the holidays, many had reopened, and we were excited to check out Melbourne’s reputable nightlife scene, even if we had no intentions of staying out past dark.

Our first stop: Naked for Satan, a solid cocktail bar with somewhat gritty ambiance and a stellar rooftop scene

Next we made our way to Black Pearl, a high-end cocktail bar on the Melbourne scene for over fifteen years and a mainstay on the World’s 50 Best Bars list. Sorry, was having too much fun and forgot to take pictures.

Our last and final (bar) stop of the night: Amarillo, which ended up being our favorite spot, if you can’t tell from the expressions of delight in this photo

Unexpectedly, the hit of the evening was Amarillo, where we were able to grab an outdoor table on the sidewalk and enjoy expertly-crafted classic cocktails alongside some modern takes on classics.

Me, posing by the laneway art by Amarillo

The hospitality was always on point and we even made friends with the two young women sitting at the table next to us. I don’t remember either of their names, but have to give them credit for a) introducing Lindsay and me to the magic that is Le Labo’s Santal 33 scent, and b) playing photographer and giving us the only pictures that we managed to take of the three of us in Melbourne.

Lindsay and Katz being cute

The Aussie ladies also deserve a shout-out for recommending our delicious dinner spot for the evening: Hazel. Located around the corner from our Airbnb, the slick restaurant featured a modern, industrial aesthetic and a simple, seasonal menu. Perfect ending to our low-key bar crawl.

But wait! That’s not it. We had to stop on our walk home when we came across this crowd of teenagers (and their parents) crowded in a laneway. Turns out it was the aftermath of a Yungblud concert. Hmm. I was definitely too old to understand.

Day Three: Yarra Valley and Carlton Wine Room

If the theme of day two in Melbourne could be described as walking and cocktails, the theme of day three could best be categorized under wine and more wine. Melbourne is located approximately an hour away from two different wine regions: the Yarra Valley and the Mornington Peninsula. There was no way I wasn’t going to hit both of them during my trip.

We booked a small group tour to the Yarra Valley from Melbourne through Dancing Kangaroo Tours. Our guide was quite sweet and did her best to engage everyone, but I’ll admit that I wasn’t all that impressed with the tour. The group was pretty large (~15 people) and none of the wineries stood out to me. It also didn’t help that it was an extremely hot day (105F) and we spent much of our time outside. On the other hand, we were happy to have blue skies given all the fires occurring in Australia.

Shot from Helen & Joey. I didn’t love their wine, but the unicorn branding was memorable at least.

While the Yarra Valley tour was a bit of a disappointment, we still had one more activity to look forward to before Katz had to fly home the following morning: dinner at The Carlton Wine Room. Offering a relaxed and homey vibe, the restaurant served seasonal, bistro-influenced dishes designed to pair with wine. Just the place to visit after a day of wine tasting, right?! In retrospect, it may have been a bit ambitious, but I still loved our experience at The Carlton Wine Room, and would recommend it without hesitation. The Yarra Valley wine tour? I’d like to go back, but would probably opt for a private or self-guided tour with a different company next time.

And just like that, our two weeks in New Zealand and Australia together had come to a close. The following day Katz would be flying back to New York, while Lindsay and I would continue on to the Mornington Peninsula for a bit more fun and wine. As sad I was to see our group trip ending, I relished all our memories and was happy that we had traveled so well together.

Loved traveling with these two and hoped to do it again soon!