With the Labor Day holiday in the States falling on a Monday this year, last weekend I decided to escape rainy Canberra and squeeze in an extra long weekend to explore Melbourne, Sydney’s food and coffee-obsessed and frankly more fashionable little sis. The city was as edgy as I had heard and its hipster, artsy, and at times Real Housewives-ish locals were incredibly hospitable and friendly. I can’t wait to go back!

In order to avoid the seemingly inevitable morning fog delays at CBR, I took an afternoon flight to MEL on Virgin Australia and then caught the SkyBus to Southern Cross Station. Upon arrival, I transferred to their free city hotel shuttle, which dropped me off at my hotel, the Melbourne Marriott, located in the CBD. The Marriott’s location was perfect and within walking distance to Chinatown, several theatres, the Melbourne Museum, and a slew of other tourist spots all within walking distance or via the city’s free tram zone. I wish traveling in and out of all major cities was this easy!

A few of my favorite spots from the weekend:

• Black Pearl. Excellent cocktails, friendly bartenders, and an absurdly attractive but unpretentious crowd. It owned up to its ranking as a top 10 bar in the world.
• Bartronica. Full disclosure: I’m horrible at video games and haven’t played one since I had a Sega Genesis; however, they have a great lineup of arcade games and their whiskey and beer lists were excellent.
• Hill of Content Bookshop. Hands down the nicest bookstore I’ve come across in Australia and reminds me of Politics and Prose in DC.
• Napier Hotel. Chicken parma with smoked kangaroo. Heaven.
• Pellegrini’s Espresso Bar. Perfect for a quick espresso or a late afternoon pasta lunch.

I love to people watch, so now for a few observations:

• The coffee is no joke amazing and you won’t find a bad cuppa.
• When shopping, smile and ask for help. Australian retail employees rarely approach shoppers – it’s not a negative – just a cultural space issue.
• Peak smugness is Melbournite men wearing overly fitted sport coats with their arm piece(s) in tow.
• Eyebrow piercings and smoking are in again. Who knew?
• Melbourne is littered with dungeon-like underground toilets that are only accessible through the narrowest of the narrow stairwells. Thankfully, they seem to be filling them in with concrete due to maintenance costs — and well they’re just creepy.

Things to do on future trips:

• Catch a game of footy,
• Find non-jammy red wine,
• Melbourne Zoo,
• Brunch in St. Kilda and observe more smugness,
• Visit Bromley&Co and find more street art,
• Attend a horse race, and
• Get a few long training rides in along the coast.