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The Adventure Begins

Bittersweet excitement

sunny 35 °C


It's hard to believe the time has come for our trip to begin. I know I'm supposed to feel excited about the start of this great adventure, and I am, just a little bit. But I'm feeling mostly sad that my love affair with Chicago has to come to an end. I've been running around like a headless chook trying to get everything organized, and I just want some time to sit, do nothing and recover. I've been in a blur of packing, selling/donating almost all of my belongings, wrapping up work, and frantically searching for a shipping company; all whilst trying to make the most of the Chicago summer with my friends. After constantly having a thousand things on my to-do list, it's weird to now switch to traveling mode.


My little cousin, Vincent, whom I'm doing the trip with, came for my last week as a Chicagoan. Amongst the packing frenzy, I was able to do some sight-seeing around the city with him. This made me to look through rose-tinted glasses and appreciate Chicago for the wonderful city it is. It has the perks of a big city, but the down-to-earth vibe of a small one. The gorgeous lakefront with the stunning skyline as a backdrop constantly reminds me what a beautiful place it is to live. I love that I haven't needed a car since living here, with the public transport well set up and running so frequently. I love all the triathlon, marathon and all the other fantastic training groups and events to choose from. But most of all, I love all the amazing friends I've made.


Before I came to the US, I had a few stereotypes in my head of Americans - the Hollywood valley girl, the redneck, and the uptight New York big-shot. But what isn't portrayed in American TV shows/movies, and less well-known is the warm, welcoming and friendly nature of the Mid-West. It may be easier for me being a foreigner, but I was quickly befriended by a lot of great people. Without realizing, I now have a strong support network of friends who are there to help me through the transition, and be sad with me about my departure. It's sad to being saying bye to my Chicago family, but as cliche as it sounds, I know it's just a "see ya later". After moving from Melbourne, I've learnt that the friendships that matter will stay strong despite the distance. With Skype, Whatsapp and other cool technology, I know that keeping in touch will be easy.


So here I am, finally embarking on The Trip of a Lifetime. I have fleeting moments of panic. I feel flickers of regret for turning down my company's offer to transfer back to Melbourne in order to embark on this journey. And I'm feeling way too old to be backpacking and "slumming" it in hostels. But, it's too late to back-out now, and I know, deep down, this is what I need. It'll be character-building, right?


Our first stop was supposed to be DC, but a few weeks ago we had to change it to Montreal because of my Visa. I was super unorganized and left to the last minute validating the grace period for staying in the States after my last day at work. I'd vaguely remembered someone telling me it was 28 days, so i wasn't too phased. To my surprise, my employer's lawyers informed me that when "legal aliens" on the E3 Visa terminate employment with their sponsor, it is advised to leave the US immediately. I couldn't quite trust the information, so I contacted a few other immigration lawyers for some second and third opinions. They all said the same thing. So three weeks out from our trip, we had to reroute the east-coast portion of our route so that I don't outstay my welcome. Knock on wood that I'll be allowed back in with no issues.

As a result of my schedule-obsession (I'm a Project Manager, afterall!), we have a pretty firm itinerary. But aside from flights and accommodation, we haven't planned anything else. That counts as spontaneity, right? Our itinerary will be:

1. Montreal
2. Boston
3. NYC
4. Washington DC
5. Glacier National Park
6. Yellowstone National Park
7. Grand Tetons
8. Seattle
9. Vancouver
10. San Fran
11. Yosemite
12. Austin
13. Orlando
14. Chile
15. Argentina
- Back to Chicago
16. Auckland
17. Melbourne

First stop, Montreal!

Posted by always_explore 17:00 Archived in USA Tagged chicago

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