>  Explore   >  Staying Classy in San Diego

San Diego is one of my favorite layovers and a top contender for favorite U.S. city. The vibe is chill, the weather is perfect, and the food is de-friggin-licious. I was lucky enough to have two 24-hour layovers here this month, including a very well-spent Memorial Day. (Did I mention how much my job rules?) And I figured while I’m hanging in America’s Finest City, I’d take a few to highlight some of my favorite San Diego things to do.


1. Eat fish tacos

Yes, seriously, this is my number one favorite thing to do in SAN. I’ve tried a ton of different restaurants and quick-stop taco shops. Lately I’ve been loving King and Queen Cantina on Kettner Blvd, just a few blocks from the waterfront. Their happy hour is good, their fish tacos are great and the spicy jalapeno cucumber margarita is To. Die. For.

The taco love is strong with this one.

2. Go hiking!

For the longest time, maybe because the beach was forefront on my mind, I failed to equate San Diego with hiking. But there is an abundance of beautiful trails from beginner to ass-kicking and they’re all worth a try in my book.

Torrey Pines State Reserve is one of my favorites and although it is easy and suitable for all ages, the views are simply breathtaking. Stop along the many vistas overlooking La Jolla coastline to snap-gram-book the surf crashing against the shore for miles and miles.

Cowles Mountain is a lot more challenging, and what it lacks in sea breeze it more than makes up for when you get to the top. See all the way from Coronado to Tijuana and everything in between. Be sure to take a photo at the top and to touch the lucky rock. If you don’t it means you never officially made it to the top, and you’ll have to hike the whole thing again for street cred.

Today I rented a car and drove 30 minutes to Poway to hike Iron Mountain Trail. It was gorgeous, bursting with wild flowers in the beginning and providing spectacular views at the top. It’s not an especially strenuous trail, but takes about 2.5 hours to the peak and back. Well worth the drive—and the walk!

A tiny fraction of the view from the top of Cowles.

The wild flowers leading you along Iron Mountain will make you feel like you're in an old timey romance novel.

And the views from the top aren't so bad.

3. Run along the waterfront

Take a right when you hit the water and watch the planes taking off and landing as you run by the airport. There’s a nice little park across from the airport on Harbor Island that takes you away from the traffic and is one of the best views of the city skyline. Or go left and run by the ships, restaurants, maritime museum and tourist trinket shops until you get to the Convention Center. Or be an over-achiever and run all the way to the Coronado Bridge.

This can all be done on bicycle or scooter, and there is no shortage of them available to rent.

4. Party in Hillcrest

This gayborhood has my heart, and Hillcrest has seen me on many a memorable but not rememberable night. Stop by Alibi, a dive bar that pours a drink so strong I ask for a plain soda water on the side to dilute, get your Karaoke fix at Flicks, stop for tacos in between at Tacos Libertad. Don’t skip out on seeing the speakeasy in the back, located just behind what looks like a meat freezer! It’s very Gatsby-esque, way more swanky than the well-lit taco shop, and very cool. Then head to Ralphs for Drake in the front and Drag in the back.

Rideshares are plentiful so don’t drink and drive, dammit.

5. Hit up La Jolla

La Jolla (pronounced La Hoya, learned that one the hard way) is a fun place to spend the day. Rent sea kayaks and check out the caves that line this famous cove. Meet the cute-ish sea lions that call the rocks home. Snorkel in the marine reserve.

Drive just a liiiiittle bit further and stop by the Torrey Pines Giliderport, where you can jump off the cliffs and paraglide over the coast. Not a fan of heights? No problem! Grab a snack and a seat on the sloped lawn and watch as the braver folk take their turns running and jumping off the ledge. It’s mesmerizing watching the colorful sails soaring through the sky, little legs dangling underneath.

Cute, but smelly.

6. Bar hop in the Gaslamp

The Gaslamp Quarter is a historic neighborhood of San Diego that boasts Victorian architecture and all you can eat, drink, and dance. Mexican food, Irish bars, beach bars, hipster bars, sushi, underground speakeasy featuring jazz bands. Whatever it is you’re craving you can find it in the Gaslamp District. Except maybe peace and quiet.

7. Go to the beach, duh.

PB, OB, Black’s, La Jolla, Dog Beach, Coronado. There are so many freaking beaches! Soak up the sun, frolic in the water, take a surf lesson or just watch some hot surfer bros (and ladies too!) from the sidelines.

8. Sunset Cliffs

In Point Loma, by Ocean beach are sandy cliffs that fall into the Pacific Ocean, creating the perfect spot for viewing a sunset. Bring some snacks and drinks, and maybe a hot date, and have yourself a picnic while you watch the sky turn pink and orange. The only problem with this natural wonder being so gorgeous and incredible is that basically everybody knows about it. Don’t expect to have the place to yourself. But is sharing an oceanside cliff and a beautiful sunset with a bunch of strangers, all taking in the same little wonder, really the worst thing in the world? Nope, I didn’t think so either.

There are a couple designated parking lots in the area and ample street parking on the side streets that line the winding, coastal cliffs.

9. Hit up a farmer’s market or festival.

There’s a farmer’s market in a San Diego neighborhood almost every day of the week, all year long. To see a list, click here.

Brewfests, taco festivals, music festivals, and don’t forget Pride! And um, hellerrr—Fleet Week! Outdoor celebrations abound in this city of eternal sunshine, and there is sure to be something fun happening when you happen to be visiting. Check out a list of events here.

10. The Waterfront Bar & Grill

A staple for airline crews who tend to stay in hotels nearby, this place is not to be missed. Unless you don’t like loud dive bars with outdoor seating, a friendly crowd, all you can eat popcorn, and beers-a-plenty on tap. (In which case, who even are you?)

The thing about the Waterfront that is so great is no matter what day of the week, there are always people there looking to socialize. All the other bars in the area could be sleepy on some random Tuesday night, and the Waterfront will end up packed with people. They’ll drink, they’ll dance, they’ll talk to strangers. It’s just a good, solid neighborhood bar. Try playing “pick out the pilots” based on their outfits while you’re there!

And there you have it. The best things to do in San Diego, according to me. I’m usually here briefly, just popping in for a 24 hour layover. The longest I’ve spent in SAN was a whole four-day stretch one Fall, before driving all the way up to coast to San Francisco. I don’t claim to be a local and have all the secrets, but who knows, maybe someday I will. Either way, these activities are perfect to keep you busy if you’re taking a trip to San Diego (and looking to fall completely in love with this city.)

Are you a native San Diegoan or do you live there now? Comment below with your insider tips! Always looking to expand my palate in this sunny city.


  • Amanda

    May 28, 2019

    Love! I’m using these tips when I’m there in July!

  • May 30, 2019

    LOVE THIS! Your writting style is so engaging. And those food photos are on point. You need to give me some tips on how to shoot food. Anddddd can we plan a campervan trip from DEN to SAN and you be our tour guide for SAN?! Say yes!!!

  • August 13, 2020

    I’m so happy to read this. This is the kind of manual that needs to be given and not the accidental misinformation that is at the other blogs. Appreciate your sharing this greatest doc.


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