Roadtrip Recap Pt 1: Seaside, Austin + Las Cruces


Day 1 – The Journey Begins

It was Friday morning and I was pretty groggy from staying up late and packing. (Because who needs more than a few hours to pack for a three-week trip? Pshh. Amateurs.) As we hopped in the car, said a tearful goodbye to Plax (ok not really, but it felt that way), and pulled out of the driveway, I don’t think it had quite hit me yet just what we were getting ourselves into.

Those first few hours we listened to music, snacked on various goodies and I may (MAY) have gotten an hour of shuteye so I wouldn’t be such a crabbypants due to my lack of sleep. Around lunch time we stopped in Talahassee so Jason could relive the days of his youth and eat lunch at his favorite stir-fry place: One Fresh. (For the record, it was my first time there and while I appreciate the concept, it wouldn’t have been my restaurant of choice.) Sidenote: Yes, I’m going to include EVERY single place we ate on our trip, probably with ample photos of food, so if you’re not into that now’s your chance to escape.

After lunch we decided it was time to actually figure out where we were sleeping for the night. We had purposefully not booked the first two nights of our trip because we were kind of torn on our first stop and wanted to make it a game time decision.

Lesson #1: Be flexible.

Keeping those first days wide open was the best way to kick off the trip in my opinion. It set the tone for adventure and spontaneity, which is what we both wanted the trip to be about in the first place.

While Jason drove, I was deep in the catacombs of several different apps/sites on my phone trying to find a really cool and affordable place for us to spend our first few days. We considered a number of things, most notably a condo in Destin,FL, a casino in Biloxi, MS, or a hotel in New Orleans, LA. After searching endless (and I mean ENDLESS) rates on VRBO,, HotelTonight, everything we could think of… still nothing was really speaking to us.

That’s when we decided to throw it up to Facebook. Jason asked his friends where we should stay between where we were and NOLA. Within minutes, multiple people had all recommended a city called Seaside. Jason and I had never heard of the city so we decided to look up photos on Google. Turns out, it was gorgeous. (And apparently also where The Truman Show was filmed… so if it was cool enough for Jim Carrey and Laura Linney, I decided it was cool enough for us.)

We suddenly got pretty excited about the idea of kicking off our trip with a relaxing beach weekend. I had actually only been to a beach in the panhandle one other time in my life despite being born in Jacksonville, so I was down to explore a completely different part of my home state.

Back to the phone I went, looking up every beachfront condo I could find on VRBO. Jason and I agreed that if we could find something ON the beach in a reasonable range, we would book it.

Lesson #2: Splurge on the things that will bring you immense value.

To us, we knew waking up to the ocean would be an ideal way to start the trip, especially given it’s what we always wish we could do from our own home, so we were willing to pay a little extra to make that happen. That’s a lesson I’ve actually learned in general from Jason over the years – you don’t have to buy it all, but you also don’t have to feel bad about treating yourself to experiences that will leave a lasting impression.

But none of that would matter if we couldn’t find a darn place to rent. I must have clicked on 100 links and suffered through more realtors’ sales pitches on the phone than I can count. As a tip, if you want to stay in Seaside, don’t bother contacting the official Seaside beach cottages rental agency. It’s something ridiculous like $500 a night. No ma’mam. Not gonna happen.

Just when we were about to give up and drive to New Orleans, I found a place that looked pretty nice, ON THE OCEAN, and in our price range. Hallelujah. Just in the nick of time too because our exit where we’d have to turn off I-10 and start making our way south to the coast was coming up literally in a matter of minutes when we found this place.

Because of the rush that the upcoming exit caused, we had to make the decision to book in a matter of seconds. Now, I’m probably the most indecisive person on the planet so to say that made me uncomfortable is an understatement, but I have to admit it felt pretty amazing to just spontaneously book an entire weekend in a city we’d both never even heard of in seconds. It was exactly the excitement we wanted to kick off our trip.

But still, we had no idea what we’d find when we arrived. As we drove closer and closer to the coast, it was like this secret little hideaway started to emerge. It was such an interesting landscape: tall, wooded areas filled with pine trees mixed with the breezy ocean air and the unmistakable markings of a beach town. We saw tons of beautiful, modern beach homes on our way into the city, and each turn we made just revealed more and more of this picturesque little town. Jason and I both commented that if we had the money, we’d build a home there in a heartbeat.

Before heading to check out our condo, we did a quick drive through the main town square. It was around 2pm and the weather was perfect. We rolled down the windows letting the brisk March air into the car, and I felt the sun beating down on my arm resting over the open car window. The only thing I kept thinking over and over was, How perfect.

Lesson #3: Don’t give up.

When we finally arrived at our condo unit, I was still pretty skeptical. The outside looked in need of a little love. But the second we opened the door, I couldn’t believe it. It was the perfect oceanside cottage I had pictured from the very moment we decided on Seaside. And to think we were SO CLOSE from giving up on finding a place.

We immediately opened the glass doors to the back patio which overlooked the beautiful Gulf waters. I took a deep breath and sighed in complete and utter gratitude. I want every person in the world to experience this feeling, I thought.

After that we headed back out to the town square for a late lunch and to do some exploring. The very first thing I spotted when I hopped out of the car was a store sign with a logo that immediately caught my eye. One step inside and it was like I was in Made Vibrant heaven.

I kid you not, it felt like if my aesthetic and personality was just turned into a retail store, this would be it. The store was called “The Art of Simple” and I was like a kid in a candy store. I wandered around just touching everything and mentally taking photos so that when I go to open my own one day (who knows, right) that I can take a page out of their book.

Lesson #4: If you appreciate someone’s craft, let them know.

As I meandered through the store, I asked the girl behind the desk if the owner was in. I loved the store so much that I just had to tell the person who’s brain it came from that I appreciated it. Has that ever happened to you? You visit a place or see a thing that speaks to you so much that you just have to say thank you?

Jason and I were introduced to Michael Granberry who owns the store with his wife. Michael worked in advertising for years as a photographer, and we got to swap travel stories while I tried to play it totally cool and act like I wasn’t OBSESSED with his store. (Okay, I might have let on a few times when I blurted out “I JUST LOVE YOUR STORE.” Who can tell.)

After we left (read: Jason dragged me out) we decided to grab some lunch from the gaggle of food trucks that were lined up right outside of the cutest little post office in all the land. I’m telling you guys, this place was straight out of a postcard.

In an effort to work off some of the delicious food truck grilled cheese, we decided to go for a sunset beach run (and by “run” I obviously mean “walk” with various one-minute run periods in between.) Watching the sun set over the calm water was a bit like a movie, and I honestly wondered if it could get any better. Spoiler alert: it could.

Later that night we decided to come back to the square because Jason was craving some fresh tacos. We had unbelievably fresh, baja-style tacos with margaritas and sangria at Bud & Alley’s Taco Bar. It was a super casual little outside taco bar that definitely hit the spot.

Thankfully, Jason also had a friend send him some restaurant recommendations in the area and since we were both hankering for something sweet, we decided to take a quick drive down to Rosemary Beach for dessert at La Crema Tapas & Chocolate. Umm…. yeah… you read that right. TAPAS. AND CHOCOLATE. Was there ever a better description of a restaurant? I think not.

Rosemary Beach is another town pretty close to Seaside – there are a group of them spanning the length of the road they call 30A. That was one of my favorite parts of our stay. The fact that you could drive such a short distance to get to a tiny beach town with a completely different feel. If Seaside was quaint, colorful, and a bit sleepy, Rosemary Beach was charming in a more European sort of way. Cobblestones, twinkly lights, rustic wood trim – it was kind of magical.

And so was La Crema. Might have been one of my favorite meals we had on the whole trip. (Yes, I’m aware it was just dessert, but in my mind that counts as a meal.) We were both still reeling from how absolutely adorable Rosemary Beach was when we sat down at our table to find our water glasses were the exact same glasses we have at home (not a common choice, mind you.) We had a good laugh about it because it was the final serendipitous piece of a day that had just gotten better and better.

Lesson #5: Just get the chocolate molten cake.

I will admit we MIGHT have gone a little overboard at La Crema, getting chocolate covered bacon AND their chocolate molten lava cake, but if you tasted both of those things, I guarantee you wouldn’t blame us.

I can say without exaggeration that our first day will be an absolute favorite day of mine for a long time to come. Maybe it was because we had no expectations for it or because it fell together so perfectly, but you couldn’t wipe the smile off my face for the entire day. It was truly such a special start to our adventure, and I’m so thankful that we left ourselves open to flexibility.

Day 2 – Seaside, FL

Day 2 started early with a 20-minute yoga session on our deck facing the ocean, led by my all time favorite yoga instructor: JASON. Our wifi was pretty spotty at the condo so instead of the 20-minute relaxation yoga video that Jas usually plays on YouTube, he just recited the whole thing from memory… IN THE EXACT VOICE of the breathy yoga instructor on the video. Frankly it didn’t end up all that relaxing because I was laughing the whole time, but at least we tried.

We got ready and decided to go out for breakfast. Since we kind of splurged a bit on dessert the night before, we decided to look up some place cheaper on Yelp, which led us to a weird little cafe sort of in the woods that doubled as a Bed & Breakfast. It made for an interesting experience, mostly because, as we sat outside in their odd little garden waiting for our food, an older gentleman on his screened-in porch behind us was chatting with who I presume to be his adult son and proceeded to just RIP A FART MID-CONVERSATION.

Yes, you read that correctly. Not like an I’m-old-and-can’t-control-my-farts-so-it-slipped fart. Like a lean-sideways-and-not-give-a-crap-about-who-hears-it,-on-purpose fart. Somebody please explain to this man that a screened porch doesn’t create an invisibility cloak, nor does it make your farts inaudible to the people quietly waiting for their food just outside. It took everything in both Jason and me not to DIE laughing. (You’ll have to forgive me for including that little tidbit from the trip, but it’s a moment I’m going to want to remember forever.) Overall the food was pretty meh and the experience as a whole was enough for me not to recommend it to you.

After the fart debacle, we decided to head back to Rosemary Beach to check out their small Saturday arts market.

That’s another thing I loved about the 30A area – so many galleries and artists. You could tell there was truly an appreciation for craftsmanship among them. We also took a half hour to just sit in their grassy park, soak up the sun, and watch the dogs play and chase each other.

By then it was getting a bit hotter so we decided to spend the afternoon laying out on the beach back by our condo. I got to finally finish my friend Pam Slim’s book, Body of Work, and had some time to just BE.

Lesson #6: Don’t force it.

In those moments, I remember feeling a little impatient with our trip because I was waiting for it to start feeling like a life-changing adventure. In the weeks leading up to our departure, I had built it up so high in my head as this experience that would rekindle my creativity and give me a renewed sense of direction. At that point in time on the beach, it was just feeling like a really awesome vacation.

When I sensed myself starting to put that kind of pressure on the trip, I tried to remember not to force it. Instead to simply be grateful for what it was shaping up to be right then and there. (You can read more about this in my newsletter email from a few weeks ago on gratitude.)

For our final dinner in Seaside, we decided to head to Alys Beach (yet another 30A town – we’re still not confident if it’s pronounced “Alice Beach” or “Allie’s Beach” so if you know, pllllease let me know in the comments) to a restaurant called George’s. George’s is definitely a bit more upscale, but the quality of the food was in line with the price. It’s one I’d recommend if you’re in the area.

Apparently we hit the city at the right time because Spring Break was just starting and our waiter told us that’s typically the mark of open season when it can get a little crazy. They had just opened up the outside deck seating at George’s so we got to enjoy another beautiful sunset with our meal. A fantastic ending to the first leg of our trip.

We returned to our condo to get some work done, and packed up for a full day of driving to Austin for SXSW.

Day 3 – Drive to Austin, TX

We woke up pretty darn early (maybe 6:30 – that’s REALLY early for me) and got ready to head out of town. Not without stopping by Charlie’s Donut Truck in Alys Beach though, which unfortunately had run out the day before by the time we got to it. With a fresh half-dozen donuts in our possession, we hit the road. (Yes, half dozen. The man loves his donuts, what can I say.) We also got to see the sunrise heading out of town which I rarely get to see.

The drive to Austin was pretty dang long and uneventful, though I was excited to start seeing some change in scenery through Mississippi and Louisiana.

We finally arrived in Austin around 6:30pm and got to meet up with our good friend Justin who runs social media for GoToMeeting. They were having a private event at the Tesla Gallery at The Domain in Austin, and Justin was kind enough to invite us. The 100% electric Tesla is something Jason and I have been increasingly interested in (mostly Jason because he loves cars), but since we don’t have a dealership in Jacksonville we’ve never had the opportunity to drive one. Until then! We got to test drive the Model S, and let me just tell you… it was incredible. So many cool features, so quiet, and crazy fast. I opted not to drive one (only because if I’m going to break things, I’d prefer they not cost more than $60K.) Anyway, Tesla is a topic for another day, but let’s just say Jason and I are officially saving up for one. We both want to contribute to humanity’s weening off of fossil fuels, and we want to do it in style. Simple as that.

Lesson #7: Make the effort to spend time with the people who make you better.

At the Tesla event, we got to hang out with some of our favorite people in the world – AJ and Melissa Leon – and the rest of the Misfit, Inc. crew, whom we love. Misfit put on the conference last year that changed our entire outlook, so we are forever grateful to them. To be honest, SXSW is great and all, but it’s a little bit of a zoo; We made the trip to Austin for the sole purpose of seeing Justin and the Misfit crew, and I was so glad to spend some quality time with them.

Despite being as crowded as you’d expect during SouthBy, Melissa and her magic managed to get our HUGE group a dinner table at Lambert’s, an upscale BBQ restaurant right in the heart of downtown. Definitely recommend. We got to have a joyful meal with friends on the patio while the Reddit party raged at the bar upstairs. How very SXSW of us, I know.

Misfit was also doing a promotion with GoToMeeting to officially launch their newest creation Twitgift to the world, and they bought an RV and parked it in the heart of downtown for the promotion. Well that RV is where we spent most of the night, all eight of us or something like that packed in this tiny thing, drinking Prosecco and talking about life, politics, business, mythology, education, the internet and everything in between to the wee hours of the morning. This was another highlight for me of our trip – just laughing and contemplating existence with some of the smartest, kindest, most genuine people I’ve ever had the pleasure to meet.

We finally got home around 3am (“home” by the way was actually the empty apartment of a friend of a friend because our original place fell through…) and decided that Austin probably wasn’t going to get any better than that, so we agreed to change up the plan and drive to Las Cruces the next day instead of spending two days in Austin like we had originally planned.

Day 4 – Drive to Las Cruces, NM

Before we left Austin to drive to Las Cruces, we still managed to return downtown for some lunch to meet up with some friends, including two of my awesome college buds – Jamie and Erin.

We decided on Las Cruces because it kind of cut our trip from Austin to Phoenix in half, and after the drive to Austin, we (and by “we” I mean the sole driver of this trip, Jason) didn’t want to do another 12-hour marathon day of driving.

People kept telling us that the drive through Texas was going to be slow and boring, but I actually really enjoyed that day of driving. There were tons of interesting little towns on the outskirts of Austin that we got to see. Jason actually started teaching me in the car how to use the “big” camera – his DSLR – and so I really enjoyed experimenting with the settings to capture parts of the drive.

About midway through the drive, I was scrolling through the Roadtrippers app on my phone (excellent road trip app for finding things!) and I came across this place called The Caverns of Sonora, considered the most beautiful cave in Texas with 95% of its formations still “growing.” Jason had never seen a cavern before and the tours were pretty reasonably priced, so we decided to make the stop of I-10.

That’s when things got interesting.

Besides being greeted with a large number of peacocks upon arrival, we were gifted with probably one of the most mind-boggling tour guide experiences of my life. Our guide was in his early twenties with a deep Texas twang. He seemed extremely knowledgeable with a light-hearted, if not repetitive, sense of humor, as is customary for those kinds of tour guides. Then his stories seemed to shift from the history of the caves to the history of his exploits with booze and women, despite the fact we were in a group with families including 6-12 year olds. At the deepest part of the cavern, hundreds of feet down, he had us literally sit on benches for 25 minutes… for no reason. “To rest,” I think he said, as he continued to tell the kids that they’ll lose all their friends when they graduate high school. I mean, you couldn’t have made up half of the stuff that came out of his mouth. Jason and I just kept exchanging glances as if to say “This crazy kid is holding us hostage at the bottom of a cave. Is this real life?”

Lesson #8: Have patience.

The walk up the stairs to the top of the cave seemed like the longest of my life. After suffering through our “rest period” where we were held captive and forced to listen to the weirdest, most inappropriate stories, we now had one man in our group with a heart condition and another woman with asthma. So on top of every single flight of stairs we had to stop and rest. (Let it be known I certainly am glad we stopped for them, it was just a comedy of errors trying to get out of there.) Jason and I just kept laughing to ourselves at the absurdity, and I had to muster every single ounce of patience in me not to go darting up the stairs yelling “Nope. SEE YA.”

Finally we made it to the top and I think Jason and I must have sped-walked away from that place. Let me just add… the caverns were BEAUTIFUL. They were completely awe-inspiring and I’m glad I had the chance to see them. However, if you ever decide to visit the Caverns of Sonora, I’d think long and hard about whether you want to be hundreds of feet underground at the mercy of someone else’s storytelling. 

We still had quite a bit of road to cover before we made it to Las Cruces, but by the time we got done with the cavern tour, the sun was going down. So many people had told us that the drive through West Texas would be like torture – long stretches with no cities in between. However, those people probably didn’t think about the fact that we would be driving West at sunset.

For two whole hours we got to chase one of the most beautiful sunsets I’ve ever seen. It was magical. That was the moment it starting feeling like a road trip. That was the moment I finally felt like yes, this is why we decided to do this.

We made it to Las Cruces around 2am and just walked right in to a hotel we had found online, Hotel Encanto. Jason asked for any last minute awesome deals and, luckily, they hooked us up. It definitely wasn’t my favorite place we stayed but it was unique, very “New Mexico” and so for that I was really happy. We went to bed and prepared for the next leg of our trip… Phoenix and Palm Springs!

I’ll be sharing the rest of our trip each day for the rest of the week if you want to check it out. If you’ve made it this far, I hope you enjoyed the recap. My goal with sharing this much detail was to hopefully make you feel like you were along for the ride. Everyone needs to take a trip like this at least once, and if you can’t plan yours yet, at least you can join ours! Until tomorrow!


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