I ‘Winged’ a Weeklong Vacation and This is What Happened

Let me preface this by saying that I am a planner. Don’t get me wrong, I love spontaneity and an adventure more than I probably should, but when it comes to trips, birthdays, and other major events, I can give even the most high-strung wedding planner a run for her money. So when my boyfriend and I decided to book tickets for a week in California, I was full of “We should do this” and “We have to book that.”

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We booked a flight into LAX for the 4th of July, and a return flight out of San Francisco a week later.  We then booked a rental car (FYI: it is SO hard to find a company that will let you up pick up and drop off at different locations, but shout out to Enterprise car rentals for being amazing), an AirBnb for the first two nights in Windsor Hills, and a gorgeous hotel for the last night in San Francisco. We planned a few activities: a day at Universal Studios and ziplining in the Redwood forest (my birthday treat from the boy). And then…we did nothing. Since he had recently moved to New York City, and I was cramming for finals, any further planning simply didn’t happen. As it turns out, that was the best thing we could have done.


We got into LA around 10:30pm, picked up our bags and the car and hightailed it to In N Out Burger (how could we not?) before heading to our home for the next two nights. After a brief dispute over how to enter our temporary home (What “white door” were the owners talking about?), we were officially settled in (near) LA! The following day, despite a small hiccup with our day passes and getting changed 17 times before leaving because “What if the forecast is wrong” (it was and I thought I was going to die), we made it to Harry Potter World—er, Universal Studios. That was followed by about an hour of traffic, empanadas, cocktails at a weird karaoke bar and an excessively expensive parking ticket that we didn’t actually find until the next day. Oops. Whatever, we were going with it.

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And then, well, we weren’t sure.  We hadn’t planned that far.  We’d discussed maybe spending the following day in LA doing touristy things, but one day of insane traffic was enough. So on a whim, we booked another AirBnb on the edge of Joshua Tree national park and headed south. Because I mean, why not? Therein lies the beauty of an unplanned trip. 

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Our reservation was in the complete opposite direction to where we were meant to be heading, but it didn’t matter because we were winging it. After lunch at an oceanside cafe in Laguna Beach suggested by Yelp and an afternoon spent exploring and dozing on Thousand Steps beach, we headed into the desert.

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The drive took slightly longer than anticipated, but our destination was so stunning that the long drive didn’t matter. (A note to the spontaneous traveler: If you ever get chance to drive through desert mountains at sunset, take it.) However, that did mean that it was pitch black by the time we were attempting to navigate small dirt roads with only our host’s monumentally vague directions to guide us.

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 Despite the twenty minute period we thought we’d just driven into an episode of Criminal Minds, we eventually arrived where we were meant to be: gorgeous hand crafted clay domes that were deceivingly roomy on the inside. 


The following day, I dragged my boyfriend’s grumpy ass out of bed at 5:00am to hike a rock formation on the outskirts of Joshua Tree National Park and watch the sunrise. (The struggles of being a morning person trying to date a night owl) This is quite possibly one of my favorite memories to date, and it still blows my mind that it would never have happened if we had actually sat down and arranged an itinerary for the trip. Who would have thought of spending a night in the middle of a desert 5 hours from LA- in the wrong direction, just because? But when the opening popped up on AirBnb, it was too cool to pass up.

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Coffee, showers, and then we were back on the road- heading to an airstream trailer in Malibu (another Air Bnb) that we had booked after arriving in Joshua Tree because it was in vaguely the right direction after our desert detour. The drive took most of the day, but again it was gorgeous; and we spent the evening sat on the beach eating the overpriced artisanal chocolate bars we had lugged all the way from Brooklyn (it’s the little things).


After breakfast on the outdoor grill (Pineapple wrapped in bacon. Try it now. Seriously.) and some frantic searching for another place to stay (the downside of having no planned accommodations), we were on the Pacific Coast Highway, finally heading north. We had booked a hotel somewhere called Morro Bay, whose claim to fame according to the internet, was a really big rock.

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This weird little town turned out to be one of the most magical places I have ever been in my life and is home to what’s left of an eroded Volcano. It was a tiny little fishing town, seemingly devoid of tourists and is at the top of my list of places that I will recommend to everyone and anyone to go visit (but only if you take me with you). Again, this is a place we had never heard of before, that we stopped at because it was on the way and we realized our wandering had left us cutting it close to when we needed to be in the Redwood forest for zip lining. 

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We spent the following night with one of Luis’s old high school friends, who he’d reached out to on a whim, before our Sunday morning zip-lining session; then headed into San Francisco. 

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Our intended night of exploring quickly devolved into a ‘nap’ from about 5:00pm to 9:00am the following day (we’ve all been there); which consisted of the best Chinese food I’ve had in my life, and sitting on the beach by the Golden Gate bridge with a really good bottle of red wine. Not a bad way to spend your last few hours somewhere if you ask me, and exactly the kind of laid back day that was needed after covering just over 500 miles in a few days. Needless to say, we were both grateful we didn’t have a barrage of scheduled activities to attend.


So yes, overall, despite a few minor hiccups in travel plans and a horrendous sunburn on my part, this trip was fantastic. And we wouldn’t have done any of the things that made it so randomly amazing if we had planned everything out. The ability to decide what you were in the mood for, Google that thing, then book somewhere nearby and go? It’s refreshing and exhilarating and my new favorite way to travel.

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So here is my advice to you: anyone still reading after my rambling about a week spent mostly in a car, stop worrying. Stop planning and over planning and be adventurous and spontaneous and a little wild. In a life that revolves around deadlines and responsibilities, a little spontaneity is good for the soul.

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That said, always over budget—way more than you think you need to. Shit is expensive, and so are random misadventures and strict parking enforcement officers. Double check times of where you are supposed to be places, then check them again because a flight at 12:00am Monday definitely means it leaves Sunday night (United Airlines is wonderful, and monumentally helpful), and book an AirBnb whenever you can. The experience is so much more unique and memorable than another beige hotel room.

Lastly, you should only ever date a person that you can spend seven days in a car with, with no idea where you are going, and still not want to murder them. Safe travels!

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