My parents instilled a sense of wanderlust in me (and my sibling) at a young age. I was barely 6 months old when I traveled to a different state by plane – Hawai’i – and I was 7 by the time I traveled to Europe for the first time.

So I’m always up for a travel adventure. I enjoy skipping about different cities and countries, some times in style, sometimes not. Exploring the touristy options as well as finding fun spots off the beaten track thrills me. Recently, I kept seeing advertisements for Remote Year on Facebook and thought how cool it would be. A year might be a little much (my work does host a huge conference, after all), but the idea of spending months working remotely and staying in places long enough to feel like you lived there sounded like a dream.

So, this summer as a I realized I had several obligations that would take me to Europe and the East Coast, I started thinking about how I could make it an exceptional summer instead of one just flying back and forth between events. I needed to visit my sibling who had moved to Ireland over a year ago, go to a wedding in NYC, a conference in DC, celebrate our 3 year anniversary and our birthdays with my boyfriend all within 2 months. That was a lot of flying across the country!

Or… I could live with said boyfriend and just make easy weekend trips. I didn’t have a rent to worry about due to lease timing. I don’t have kids to take care of. I have a job that requires Internet, not physical items.

I began talking with my boss about how I could possibly work remotely for 2.5 months. Now, I definitely had a good starting point since my organization as a whole works remotely 3 days of the week, but there are some large projects happening this summer and early fall we had to consider. By February, we had a plan in place. I would stay for our organization’s all staff week, then be back in time before things got super busy with our conference planning. With the job on board, I started planning the places I’d go.

The final list included:

• Dublin (free, thanks to my sibling who let me stay there for 2 weeks AND let my best friend, hereafter referred to BFF, come for a week)
• Amsterdam (weekend holiday while in Ireland – quick easy flight and a hostel)
• DC (work conference – paid hotel room, thank you work!)
• Richmond (Boyfriend)
• NYC (Airbnb, so we don’t have to eat out every night for the whole week)
• Delaware (boyfriend’s family house)
• Hampton (birthplace of NASA – day trip from Richmond)
• Montreal (flight with points and an hostel)
• Minneapolis (staying with a friend)

I left two weeks ago, and it’s been a whirlwind already! I’ve hit a pretty big snag already – more about that in a couple of posts – but here’s what I’ve learned so far.

• Packing for this long with so many different climates and occasions – work, touristy things, romance, wedding, beach days, etc. I’m a solid packer, but I don’t feel like this was a particularly effective example of my skills. That being said,
• Packing cubes are your best friends. Not only do they keep you organized – I was able to put my clothes for Ireland and Amsterdam in one cube and just unpack that during leg 1 – but if your scale should give you a different weight than the airport scale does (yikes!) it’s easier to take 5 pounds out of your checked suitcase if you can just grab those cubes. Yes, yes I did need to take out my folded up, packed weekend bag to carry the extra weight onto the plane.
• CLEAR, the new security scanner, is worth every penny for a subscription. If you want to travel a lot, this will help you bypass the longer security lines. It saves you a lot of time, which becomes important when you’re catching planes all the time. Plus, it’s hard not to feel like a boss when you get escorted passed the ID checking security folk.
• No matter how well you plan – and trust me, I had everything scheduled to a T (except my flight home) – you have to be okay with it all falling apart. If you’re not ready to embrace a true adventure, Bilbo, don’t take that step out your front door.
• Friends to call on will be your saviors when things do fall apart. Trust that people who love you will catch you when you need them.
• If you want the shoes, buy the damn shoes. Oh wait, that’s a life lesson, not a travel one!

I’ll recap my last two weeks in up-coming posts, then keep you all updated more often moving forward.