The United States of America

The East and West coasts in three weeks

My cousin was getting married in Los Angeles, so what was there to do but hop on a jumbo jet headed for the gulag known as Los Angeles International Airport and try to get through customs without being patted down too many times by surly customs officers?

My packing list:

  • A big empty suitcase
  • Bathers (because nobody likes shopping for bathers)
  • My GE Money credit card

Pro Tip #1: Wear thongs or shoes that slip off easily. They’ll make you take off your shoes at many security check points, so you might as well prepare for the worst.

I had grand plans on this particular getaway – to see the big cities of the east coast, particularly Chicago, Philadelphia and Boston. I was also going back to New York, Washington and Hawaii, just because.

First stop: Chicago.

I wanted to visit the Windy City so much, simply because I’d just finished watching HBO’s Boardwalk Empire, and wanted some context. I did the guided “Southside Gangster Bicycle Tour” with Bobby’s Bike Hike, and I wasn’t disappointed. We stopped by the Holy Name Cathedral, to see the bullet hole-ridden cornerstone, where North Side Gang leader Hymie Weiss was gunned down with a machine gun. We also cycled through Chinatown and the old Red Light District, where old-time mafioso still hung out.

Pro Tip #2: Try Chicago’s deep pan pizza – it’s disgustingly heavy, but worth a try for the taste, which is very cheesy and generally delicious. We went to Lou Malnati’s in Wicker Park on the basis of several local recommendations.

Deep dish – eat with cutlery!

We stayed in hip Bucktown at a very cute little first-floor flat that we booked on AirBnB. This place had one rating, but nonetheless I took a chance, and it was great! Our hosts were a lovely young couple with great taste, and the very chic apartment had two bedrooms, a renovated pocket-sized bathroom, a small kitchen, dining room and cosy living area with a record player.

Pro Tip #3: Get free travel credits on your first AirBnB booking by signing up for an account using this link:

Just a short walk from the apartment was North Damen Avenue, which had a great Mexican restaurant called Big Star, and a couple of very Melbourne-like bars, hidden behind unmarked doors. In fact, Bucktown and neighbouring Wicker Park brimmed with street art, grungy record stores and vegan cafes so we felt right at home. Sometimes the place felt so like home, that I was often rudely jolted back to reality by a “no guns” sticker on a shop entrance, doughnuts at breakfast or getting on a bus (going the wrong way) only to find myself in a gritty neighbourhood where my pale skin stood out like a beacon.

Chicago sure can donut – stores are everywhere and they eat ’em for brekkie.

Next: Boston

Boston has a real moneyed air about it – particularly the Back Bay area, where we had arranged a basement apartment in a handsome 19th century brownstone. The place was huge – two levels of simple, yet upscale residential space. Steps from the property was a Tremont Street – a trendy suburban shopping strip with heaps of great local restaurants and boutiques.

After walking all the way around the neighbourhood, up to Boylston Street and browsing the farmers’ market at Copley Place, we decided to pick up a car and go see America’s “brain trust” – Cambridge, home to Harvard and MIT. Really, it would probably have been more interesting to have walked the campuses – driving around both complexes was like cruising around the University of Melbourne perimeters, with a LOT more traffic and crowds of students to navigate past.

Back in town, we settled down for a drink at the base of the swanky Ritz Carlton, near the sprawling Boston Common, a leafy green park filled with joggers, boot campers, school groups and tourists on a sunny day.

Pro Tip #4: Have ice cream! The good people of New England (Massachusetts, Maine, Vermont; basically all the places in the US of A where they don’t end words ending with “r” with a hard “ARRR”) consume gallons of the stuff, and hey, they invented Ben & Jerry’s and Baskin Robbins. Read this article on where to find the best scoop shops:

We spent the following day following a man dressed as a 17th century town crier around the city, learning about its history. To be entirely truthful, it was pretty boring as we didn’t know a great deal about American early history – other than general facts about key people or events such as Benjamin Franklin and the Salem witch hunt. Poking around King’s Chapel cemetery was interesting because the headstones were so old and their inscriptions fascinating –  unfortunately, we didn’t know much about the first people who came off the Plymouth ship nor about Puritanism.

Pro Tip #4: Faneuil Hall is worth a look – the place where Samuel Adams made his famous speech to rouse his countrymen to break away from Great Britain, this landmark is a vibrant marketplace, filled with shops, eateries and boutiques.  

Chocolate craziness at Faneuil Hall

Before we knew it, we were on the comfortable Amtrak Acela Express which left to New York City. The journey took about 3.5 hours, but with free Wi-Fi and power points on board as well as pretty views of New England, time flew by.

Destination: New York City

The thing about trains in America is that you don’t encounter any traffic, and you always end up right in the middle of the city. We emerged from our warm carriage in the heart of Grand Central Station – a place which never gets old – where we flagged down a yellow cab to take us to our rooftop unit in an elegant brownstone terrace home on East 49th street.


Pro Tip #5: If you ever stay in a New York brownstone, remember that all the old buildings are walk-ups, so travel light and be prepared to climb a lot of stairs.

So, because we’d been to New York before, this time round we decided only to see one Broadway show – Les Miserables, go for a run all around Central Park with a detour through F.A.O. Schwarz, wander the fancy streets of the Upper East Side, buy a Proenza Schouler PS1 handbag and try a burger and frozen custard from Shake Shack.

If I had more time, I would probably have gone to walk the High Line, slurped some oysters at the bar at Grand Central and maybe seen another show – The Book of Mormon, if I could magically have gotten some tickets at the last minute.

It’s hard not to feel patriotic in the middle of Times Square.

Then it was time to say goodbye to the Big Apple. Given there were four of us, we opted to hire a car – and navigate Manhattan late morning traffic (not too scary, I might add) – down to our next destination, Washington DC. The road trip would give us a chance to do two things:

  1. Go shopping at a factory outlet*
  2. See Philadelphia

*Pro Tip #6: Had I been more organised, I would’ve shopped online before I arrived in the US of A and had everything delivered to one of my addresses. That would probably give me a chance to try it, then exchange or return it if it didn’t fit! There aren’t many factory outlets in the downtown areas of Boston, Washington or NYC so if you’re after a bargain, internet shopping is your best bet.

In Philly, we got out to see the Liberty Bell and to try a Philly steak sandwich – it’s basically a beefy cheesy sanger. Then we made our leisurely way down to the capital, where our Airbnb two storey townhouse awaited.

Meaty, cheesy goodness.

Washington DC

Washington DC is a refreshing change from New York in that almost all the sights are free. The biggest difficulty is choosing which to go to. On my last trip, I did Congress, The Mall including going up the Washington Monument and Postal Museum. That time we also stayed at the kooky Kimpton Hotel next to Union  Station. All great and we got everywhere on bike share bicycles.

This time, I opted to watch US dollars get printed at The Mint and wander the Holocaust Museum. Having studied World War II in depth at university, I managed to lose half a day here. Then it was off to the International Spy Museum near Chinatown, where I listened in on Russians and “got shot” when I made too much noise in the air vent I’d crawled into.

Pro Tip #7: I’d be pretty careful with picking where to stay in DC as many neighbourhoods are a little sketchy in terms of safety. The U Street area might be famous, but it felt pretty dodgy.

We flew back to LA thereafter, to a world of six lane freeways where traffic was a health hazard. After the wedding and family obligations, it was off to Oahu, where we booked a lovely flat with a big balcony above the iconic beachfront Ilikai Hotel (of Hawaii Five-0 fame).

Our place in the Ilikai. Image courtesy of AirBnB.

Remember that if you haven’t already signed up to AirBnB, you can get free credits to put towards your first booking by signing up via this link: ($50 at time of writing). Some people have had negative experiences booking on the site – personally, I haven’t but I am admittedly extremely fussy with what I book!


Waikiki Beach is nice in the sense that it’s like the Gold Coast. Glitzy and full of high rise condos, the place is literally built for tourists. Also, it sits in the shadow of Diamond Head.

Pro Tip #8: Stand up paddle boarding off Waikiki Beach might get you great photos but be aware which way the wind is blowing. This is not a beginner stretch of water.

The lagoon in front of Turtle Bay Resort was a lot more forgiving for stand up paddleboarding.

We rented a car to see more of the island and sure enough, after a day in the city, we were poking around for something active to do. Off we went to North Shore, for a spot of scuba diving.

Whilst we got to do a shore entry (my second) and swim through various interesting volcanic looking caves, be warned that visibility up here isn’t great as there’s massive swell that stirs up the sand. This made sense when I read later that all the big wave surfers come up here for the fearsome Banzai Pipeline reef break.

The water’s sandy but North Shore provides a good intro to cave diving.

We also stopped in at Turtle Bay Resort for a Segway tour, which uncovered a large Hawaiian monk seal – a native species and rare sight sadly, as their population is in decline. AMAZING!

Kept a respectful distance so I wouldn’t interrupt his nap!

Pro Tip #9: If I could do this trip again, I’d probably have booked a night or two outside of Waikiki Beach – possibly at Turtle Bay – just so I could enjoy a break from the clamour of city life. Or I’d fly to Kauai or Maui for something different.

Then, with a suitcase full of new stuff from runners to boots and bras, it was time to go home to Vegemite toast, decent coffee and people who understood my English.

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