There Are Worse Ways to Turn 30: My Birthday Trip to San Diego

For the next blog post or two, I’m going to veer away from my long-running story about my travels in South America last year. But don’t worry — I WILL be writing up posts on the rest of those adventures soon! For now, though, I have other fun stories to tell you…


For the past few years, I’ve given a decent amount of thought to how I wanted to ring in my 30s. I knew I wanted to be traveling, and I knew I wanted to be somewhere warmer than Chicago. Having a December birthday is fun, but with the exception of my 27th birthday in New Zealand, my birthdays are almost always cold and snowy.

Planning a trip to a foreign country seemed too daunting with my new job, and also a little too expensive. So as Logan and I brainstormed potential destinations, one particular locale began to stand out: Southern California. We kind of fell in love there when we went to Coachella four months into our relationship. It’s warm all year round. And, frankly, it’s somewhere we might want to move one day (everyone who knows me knows I’ve been trying to move to California for years now…).

We decided to spend the week in San Diego with the intention not only to enjoy the weather and the seafood, but also to explore the area to see if it might be a good fit for us in the future. And let me tell you: I fell in love.

We boarded a flight on Saturday morning, leaving behind the cold, wintry weather of Chicago. Until that week, it had been a very mild early winter — it finally got really cold right before we left for California.

Another major weather event threatened to derail our plans, too: The wildfires that were raging across Southern California. Though a few fires had reached into San Diego County, it appeared that La Jolla, where we’d be staying, was unaffected.

We landed in San Diego, checked out our rental car, and set the GPS for our Airbnb in La Jolla. Even the 20-minute drive to the Airbnb was pleasant. Logan said, almost immediately, “Let’s move here. It just feels right.”

Our Airbnb was about as dreamy as it gets for $80 a night. The top floor of a converted single-family home in La Jolla, it had a rooftop porch that was perfect for watching the sun rise and set over the ocean. It was the perfect spot for our daily morning ritual: Books and coffee (yes, we do that every weekday morning here in Chicago).

Because of the time difference, our bodies naturally woke up at 6 a.m. every morning of our trip, giving us plenty of time to sit in the porch and watch the sun come up. By 7 or so, the weather would start getting warm… We had absolutely PERFECT weather (not that anything else exists in San Diego) with daytime temps reaching the mid-70s, dipping down into the low 50s at night.

Since we arrived in San Diego around 2 p.m., we had a half a day to explore La Jolla. Our first stop, naturally, was the Taco Stand, a little joint just down the street that had nine or ten people lined up outside waiting for tacos. The tacos were delicious, by the way.

(A side note: Logan and my second-favorite tradition, right after our morning books and coffee routine, is taco Fridays. So we eat *a lot* of tacos.)

We wandered around for the remainder of the evening before stopping at a little hookah bar for happy hour (we passed on the hookah). We watched the sun set over La Jolla before managing to stumble upon a restaurant called Herringbone, where I introduced Logan to oysters — his life was forever changed — and we enjoyed an indulgent birthday-week meal of seafood, bread and wine.

The next day dawned bright and early, and we headed out for Sunday brunch at a restaurant called Breakfast Republic in the North Park neighborhood. When I visit a new city, my first priority is to figure out where the hipsters live and descend upon their neighborhood to get a taste for the local dining and art scene. North Park is apparently San Diego’s equivalent of Logan Square, so that’s where we headed… And boy, we were *not* disappointed by our brunch. Breakfast Republic had all of the Paleo, gluten-free, and healthy options you could ever imagine, but they were hardly dainty diet food. We were full all day.

After wandering around North Park and checking out an open house in the area (yet another one of our favorite things to do together), we drove back to our Airbnb to regroup. Logan had been interested in taking a drive up to Del Mar, a seaside town just north of San Diego that has a reputation for being a fantastic beach/surfing destination. We hopped in the car and cruised north.

Del Mar was upscale. Like, really upscale… We passed an average-sized seaside house that was listed for $7 million. The town was clean and pretty, and we absolutely loved the look and feel of the beach. Surfers dotted the ocean and people lazed around on the beach and the grassy park beyond. We grabbed some fresh juice and kombucha from a little juicery down the way before heading back south.

We decided to get dinner in Little Italy, a neighborhood of San Diego proper. The downtown section of San Diego was a lot smaller than I’d envisioned, especially being used to a huge downtown like the Loop in Chicago. But Little Italy was cute, the Italian dinner was delicious (squid ink linguine for me, veal ravioli for Logan), and we spent our post-dinner evening walking around the neighborhood eating gelato and admiring the Christmas lights.

The next morning, we woke up early and got acai bowls for breakfast before venturing out to Torrey Pines State Park. We had spotted the park, which ran alongside the beach and also had plenty of big hills and hiking paths, on our trip to Del Mar the day before and had vowed to come back to do some hiking. The morning was supremely gorgeous, and we could not have been happier with our decision. It struck us both that living in Chicago, chances to reconnect with nature are few and far between. People living somewhere like San Diego have beaches, hiking trails, deserts and campsites right within the city limits.

After eating a picnic lunch on our hike, we drove our car back to La Jolla and took a public bus down to Pacific Beach. The Pacific/Mission Beach area was the only place in San Diego that left me slightly disappointed. It seemed dirty and not particularly exciting — at least the beaches in LA, while definitely dirty, had more going on. But nonetheless, we had a beer at a little bar next to the ocean and snacked on a few appetizers before catching the bus home.

That night, it was sushi for dinner and an early night for us. We had to be up 6 a.m. the next morning to leave for a mystery destination. My birthday gift from Logan was a surprise trip to an unknown place, where I was assured we’d have a great adventure and birthday celebration. I had no idea where we were headed, but I was excited to find out.

The next morning, as we hurriedly packed and started the hour-and-a-half drive to our destination, it became clear that we were heading to Catalina Island (okay, if I’m being honest, I didn’t quite figure it out until we were basically on the boat). The ferry from Dana Point to Avalon took about an hour, and gave me strong nostalgia for my days ferrying around Fiji.

When we arrived in Avalon, I was immediately escorted to my first surprise of the day: Electric biking around the island. This was something Logan had done when he traveled to Catalina with his family, and he was pretty excited to do it again. Logan is like a kid in a candy store when it comes to activities like biking or skateboarding, and at first I could barely keep up with him. Biking around the island was actually a ton of fun, though. Catalina is a bit touristy, but it’s saved by its down-to-earth vibe. We explored the streets behind the shops where the locals live, enjoying the walkable layout, narrow streets (the main mode of transportation in Catalina is a golf cart), colorful buildings, and gorgeous scenery.

That night, we dined at the Lobster Trap, a local favorite known for — you guessed it — lobster. That night, Logan also revealed to me the big surprise in store for the next day (my actual birthday): We were going to learn how to scuba dive!

Unfortunately, it wasn’t meant to be. The next morning, while gearing up for our lesson, I spoke with our instructor about the pain in my left ear I’d been experiencing for weeks. In case you don’t know, ear problems = no diving. The pressure underwater is too great.

So, that was a disappointment. But we came up with an alternative plan: Ziplining and snorkeling. We tried a zipline track called Aerial Adventures in which you zipline from obstacle to obstacle. It was a ton of fun (if a little challenging) and was only bested by our subsequent snorkeling adventure, during which we saw hundreds of colorful fish and, in my case, a baby seal!

We caught the ferry back to Dana Point on the evening of my birthday, and were planning to spend our last night in San Diego in the Gaslamp District, an area with tons of nightlife and dining options. But by the time we arrived back at our Airbnb, we were exhausted. We had crammed a ton of activity into our short week, and we were both more in the mood to sleep than to party.

We didn’t end up partying that night, but we did manage to drag ourselves to a last-minute dinner reservation back in Little Italy. In the end, I’m glad we forced ourselves to go. It was my birthday, after all, and we ended up enjoying a truly fresh seafood platter complete with oysters (my fave), shrimp, lobster and ceviche.

The next morning, we had time for one last drive past Seal Beach before we had to return our rental car and fly back to chilly Chicago. Our time in San Diego was so… Dreamy. Dreamy is just the perfect word for it. It was absolutely the best way I could’ve possibly rung in this next decade of my life, with my love by my side in the warm, breezy weather of Southern California. Will we ever make that long-desired move to California? I don’t know, but I DO know that I’m more excited than ever to have a lifetime of fantastic adventures with this guy.

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