Number 14 on my bucket list is, “Fly somewhere on a whim“. Here’s what I was thinking of when I put it on the list:
Me: What do you want for dinner?

DC (Dinner companion): Not sure, why don’t you pick?

Me: Hmm…I feel like Italian <easily swappable with any other cuisine I may be craving>.

DC: Italian sounds good. Where do you want to go?

Me: Let’s go all out and go directly to the source. Let’s take the next flight to Italy.

Boom.

Ok, maybe not that extreme…maybe more extreme. Maybe we go to the airport with bags packed and roll dice to figure out what plane to get on. (And we’d stay for a few days if we’re going to go that far, of course.) But you get the picture. This item screams spontaneity! And it also implies success: it means being able to walk up to a ticket counter and being able to afford whatever that very, very, very last-minute fare would cost along with other associated costs and it also means having the flexibility to rearrange your schedule to accommodate.

Kind of like this video.

http://youtu.be/teAB_8dqEVs

Except, it’s a tad easier when your destination is picked for you. What do you do when you have to pick your destination yourself? That’s what (kinda) happened today.

I love to travel but my bank account doesn’t always agree with my adventures. Recently I’ve really gotten into reading all of these travel hacking blogs. These people are really smart about the way they travel and have the best grasp on how to maximize your dollars and points to take you further, in terms of distance and value. So when I saw a post by The Flight Deal with “United – Starting at $149: US – Europe/India/Israel/Middle East/Australia. Roundtrip, including all taxes“, I stopped everything I was doing–and I was about to eat lunch, so that’s a HUGE deal–I read the post and I started plotting.

Did it sound too good to be true? Of course it did, but it also felt like deja vu. It reminded me of the time I went to New York for under $130, roundtrip from Portland. Since that trip ended up working out, I thought that there might be a small chance that this one could do. After New York, I had a bunch of people telling me that they would have come with if I let them know, so this time I actually thought about who else would want to go on a random trip–and who could commit quickly, given that we had no idea how long the fares would be around. Thanks to my most recent adventure to Peru, I didn’t have to think too hard and Beau and Urvi were in!

The blog post outlined the best timeframe to consider (mid-February sounded like a good time to take a break to us, especially in the dead of the winter), but where to go? Also, Beau and Urvi live on the east coast, I’m on the west coast, so we’d have to find a destination that would work with all of our schedules, travel plans and we’d all enjoy. In the end we went for cheap (airfare), level of intrigue and not freezing…so, Tel Aviv? We booked our flights, knowing that there was a possibility that it wouldn’t work out, and waited.

And waited. And waited.

While waiting, I got to thinking, what did I learn from all of this?

1. Having a partner in crime (or travel) who is down for adventure at any given moment is rare. Find these people and hold them close. I know I made it sound like I took the bait pretty easily on this deal, and I did, but it’s taken me a while to get here. To book spur of the moment trips. To understand and pounce on good value when I see it. To turn my travel aspirations into a reality. So when I ask other people if they want to join me, I’m not surprised by their skepticism or uncertainty. We all lead different lifestyles and have different schedules and interests, that’s just reality. But then your friends say, “Let’s do it. I’m in. Just tell me when and where.” and I’m left in that moment where you pinch yourself and wonder, “Are we really about to do this?” I guess I must be rubbing off on my friends or they’re just as crazy as I am. Then again, maybe we’re all getting the do-it-while-you-can-before-you-have-kids itch? Either way, I’m glad I found people to travel with! (I wonder if I would have booked a trip if it was just me going–I’d like to think that I would have.)

2. Have an idea of where you’d want to go–and where you wouldn’t pay to go, no matter how cheap. Looking at the list of possible destinations, there weren’t any that stuck out as OMG WE HAVE TO GO! But there were a bunch that we thought would be cool to check out. Factor in the weather, and it gave us a shorter list to pick from, which we then narrowed down by cost and value. (FYI, we booked our flights for 1/3 of what other travel sites were showing us.) I think it’s time for me to start working on my travel Pinterest boards and my Airbnb wish lists so next time I have a list to reference. As nice as it is to know where you want to go, it’s equally as important to know where you wouldn’t want to go, it makes making decisions that much easier.

3. I really get this incredible rush from booking trips. If I was in denial or unaware before, there’s no hiding it now. Travel is a passion that runs through my blood. I literally had 2 computers up, with 2 browsers open on each, with a total of 19 tabs going, had my phone on speaker, was texting another friend and chatting online with a third when figuring out where to go. It took us about an hour and a bit to get it all figured out, but we did, yet here I am 10 hours later, still on a rush (mixed with a little bit of anxiety of if this is really going to work…)

In the end, I’d say it’s totally worth it. I’m definitely in that space where I’m excited about the possibility but don’t want to get too excited in case it doesn’t work out…

So, what would you have done? Where would you have gone? (If you would have been down to go somewhere together, maybe you should be on my travel buddy list for the next time :))

P.S. Just checked my email and our confirmations, we are officially ticketed! Tel Aviv, here we come! To all of my friends in Israel and all of my friends who have been to Israel, mark your calendars and start sharing your advice with us!