How I Scored a Trip to San Diego for Two for Under $500

We booked a last-minute trip to San Diego from Fort Lauderdale. Why? Two words: Birthday. Vacation. Jorge was turning another year hotter, and we never miss a chance to turn a celebration into a getaway.

The second reason? My Alaska Airlines Visa Signature® Credit Card.
Every year, I get a companion fare deal—basically, Jorge flies with me for just $99 plus taxes and fees. This little perk was about to expire, and I refuse to let free(ish) flights die on my watch.

So, I jumped online and hunted for a flight that would give me the most value. Rule of thumb: use your companion fare on long-distance flights. The further you fly, the more you save. We flew from Fort Lauderdale (FLL) to San Diego (SAN) for $493 total. That’s right. Two people. Round trip.

Here’s the breakdown:

• My ticket (Main Fare): $303 plus $53 in taxes and fees
• Jorge’s ticket (Companion Fare): $99 plus $38 in taxes and fees
  Grand total: $493 for both of us

I chose the Main Fare not just for the seat assignment perks, but because Jorge is AAdvantage Executive Platinum with American Airlines. Since Alaska and American are buddies in the Oneworld alliance, his status qualifies him and a guest (hi, I’m the guest 😝) for a First Class upgrade, but only on Main Fare tickets or higher. No dice if you're flying Saver.

Thanks to this little hack, we got bumped to First Class on our return flight to Fort Lauderdale. Fancy, right? Well, it would’ve been…

Except our flight was delayed. Why? Because the cabin smelled like fish🐠. Yep. They couldn’t figure out where it was coming from, and let’s just say Eau de Mystery Seafood is not what you want lingering for hours in a recycled air tube.

They aired the plane out for over an hour, then finally boarded us. But the smell? It stayed. We flew across the country in First Class with warm nuts, comfy seats—and five hours of fish aroma. So, was it worth upgrading? I mean… yes. It was still free afterall.

San Diego in 72 Hours: What We Did

Day One: Boozy Beginnings and a Hidden Bar

We landed around noon, grabbed a rental car for just $50 for the entire stay (yes, really), and headed to the hotel. We stayed at The Guild Hotel that was perfectly placed for all of our adventures. Thanks to my Marriott status, our welcome drinks were free. That’s a perk I’ll never get tired of.

Dinner was at Born & Raised, where the prices are high but the steaks are higher quality. We sat outside next to a floral waterfall like we were living in a rom-com. We shared the steak sampler, a white asparagus special, and got drinks from a tableside cocktail cart because, of course.

After dinner, we drove to Sunset Cliffs to catch the... well, clouds. Not quite the dramatic sunset we hoped for, but it was still peaceful and romantic. Think of it as moody coastal vibes.

To end the night, we hunted down the Prohibition Lounge. A legit speakeasy that's disguised as a law office from the outside. We made it in right when they opened and caught a mini cocktail demo with Leif, who could teach a masterclass in both mixology and friendliness. Check their site for themed cocktail events if you're planning a visit.

Day Two: Koala's and Dumplings

We started with breakfast at the hotel, then headed straight to the San Diego Zoo. It’s massive. Like, wear-your-good-walking-shoes massive.

We kicked things off with the guided bus tour included in your ticket. Pro tip: Sit on the left side of the bus for the best views (left side walking in, right side when seated).

Then, I pulled up the zoo app and made a plan. We tracked down all our must-see animals: red pandas (I could’ve watched it all day), penguins (naturally), fennec foxes (ridiculously cute), koalas (actual stuffed animals in disguise) and so many more.

Midway through, we stopped for a snack and a drink to refuel. We expected theme park pricing—but this? It was more expensive than snacking around Disney. Two drinks, two snacks, and we were suddenly contemplating selling stock. It was tasty, but let’s just say it came with a side of financial regret.

We wrapped things up with the Skyfari® Aerial Tram, sponsored by Alaska Airlines coincidentally. The tram gave us a bird’s-eye view of the park and a much-needed break for our feet.

Dinner was at Din Tai Fung. If you’ve followed us for a while, you know we visited their Tokyo location. The San Diego branch was packed, but the food lived up to the memory. Soup dumplings are still the main character.

Day Three: Wine, More Wine, and a Chemistry Class Disguised as Wine Tasting

We took the scenic drive to Temecula for a day of wine tasting, about an hour. First stop: Lorenzi Estate Vineyards. We were the first ones there (shocking, I know), we signed up for the tour plus a patio tasting with charcuterie. Their Adam & Eve red made it into our suitcase 🍷.

Next up: Lorimar Winery. We walked the grounds while enjoying six tastings. The cabernet stole the show.

Then we visited Chapin Family Vineyards and met the owner, Steve Chapin. He gave us a behind-the-scenes tour and busted out a Sommelier Wine Aroma Kit to test our Sommelier potential. I’ve never been so excited to be quizzed on fruit smells. We followed that up with a food and wine pairing that ended with pistachio chocolate and dessert wine. Bliss.

Our final stop: BOTTAIA Winery. This wasn’t just wine tasting—it was wine science. We signed up for their Wine Blending Lab, where we tasted four varietals and mixed our own blends. After picking our favorite, we bottled it, decorated the label, and brought it home. It needs to age for about a year, so we’ll pop it open for Jorge’s 40th. If it’s terrible, we’ll just say it has "earthy notes."

Final Thoughts

This trip cost under $500 in airfare for two people, all thanks to the Alaska Airlines Visa Signature® Credit Card companion fare. That one perk has saved us hundreds every year and not using it feels like throwing money into a volcano.

If you live on the East Coast and want to explore the West Coast (or vice versa) without breaking the bank, this is your move. Just make sure you book before that companion fare expires. Trust me, future you will be high-fiving present you all the way down the jet bridge.

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