Every year, my wife and I set off on a journey to celebrate our anniversary. This year, after going back and forth between a few different destinations, we finally settled on San Diego. It checked all the boxes: close enough for a quick 55-minute flight, familiar without feeling repetitive, and relaxed in a way that makes you feel you’re doing it right even if you don’t do much at all.
San Diego works for us because there’s always enough to do if we want to stay busy—but with the ocean never far away, there’s no guilt in slowing things down. You can spend an entire afternoon doing nothing more than watching the light change over the water, and somehow that still feels like a full day.
We didn’t arrive with a rigid plan or a color-coded itinerary. This trip was about celebrating an anniversary and giving ourselves permission to move at an easier pace—something San Diego seems to encourage without trying too hard. Sunshine helps. So does the ocean. Mostly, though, it was the sense that there was no urgency to rush to the next thing.
Coronado Island and a Happy Little Accident
After arriving, our first stop was Coronado Island. Normally, this is where I’d tell you about breakfast at a place we’ve enjoyed in the past—Little Frenchie—except that isn’t what I booked. Instead, I somehow managed to make a reservation for an outdoor table at The Henry.
Like Bob Ross would say, let’s call it a happy little accident.
We were pleasantly surprised. The food was solid, the setting relaxed, and the experience felt like an easy way to ease into the weekend. A complimentary glass of anniversary prosecco didn’t hurt either. It wasn’t what we planned, but that ended up setting the tone for the entire trip in the best possible way.
After breakfast, we took a short walk toward the Hotel del Coronado. Even if you’ve seen it more times than you can count, the Del still has a way of stopping you for a moment. It’s part history, part spectacle, and somehow still feels grounded by the beach it sits on—equal parts landmark and living postcard.
Liberty Station: Familiar and Comfortable
From Coronado, we made our way to Liberty Station to check in. It’s a place we almost always gravitate toward when we’re in San Diego, and part of that pull is personal. My old Navy days make the area feel familiar in a way that’s hard to explain unless you’ve spent time there.
Liberty Station was once a working naval boot camp and training center, and while the uniforms and routines are long gone, the bones of the place remain. Today it’s been thoughtfully reimagined into a collection of hotels, shops, restaurants, and open public spaces. Wide walkways, historic buildings, and an unhurried pace give it a sense of calm that’s often missing in more tourist-heavy areas. It’s a place that encourages wandering without an agenda.
That evening, we kept things simple with wine and a cheese plate at Carruth Cellars. It wasn’t a big, elaborate dinner, but it didn’t need to be. Good wine, something easy to snack on, and the feeling that the weekend had officially begun made it more than enough.
Belmont Park, Minus the Coffee
The next morning, we drove up to Belmont Park with a simple goal: walk the boardwalk, grab a coffee, and watch the ocean. Walking happened. The ocean showed up, right on cue. Coffee, somehow, did not.
This remains one of life’s small mysteries—how a place like Belmont Park doesn’t have a great option for quick, takeout coffee. We looked. We walked. And eventually, we gave up.
We did get a little tourist shopping in. Sometimes a plan doesn’t pan out, and that’s okay.
Breakfast, Take One
By late morning, we found ourselves back downtown along the Embarcadero and stopped at Malibu Farm for a late breakfast. It was… fine. Nothing bad, nothing particularly memorable. Sometimes a meal simply fills the space between experiences, and this was one of those times.
Thankfully, breakfast redemption was waiting.
Anniversary Dinner, with Mixed Reviews
That evening, we headed to Rare Society in University Heights for what was meant to be our main anniversary dinner. There’s a Rare Society location in Las Vegas that we’ve been meaning to try, so giving the San Diego sister restaurant a shot felt like a good excuse to finally see what it was all about.
The food was good—solid, well-prepared, and clearly the kind of menu built for people who appreciate a classic steakhouse experience with a modern edge. As far as the meal itself went, there wasn’t much to complain about.
The seating, though, told a different story.
We were placed at a small two-person table right in the middle of the restaurant. For an anniversary dinner, it wasn’t exactly romantic. The energy was lively and the room was buzzing, but it felt more like being dropped into the center of the action than tucked away for a quieter, celebratory meal.
It didn’t ruin the night by any means—but it reinforced something we’ve learned over time: atmosphere matters just as much as what’s on the plate, especially on a trip meant to slow things down.
Breakfast, Done Right
The following morning, we headed to Farmer’s Bottega in the Mission Hills neighborhood, and this one absolutely delivered. A locals kinda place—not flashy, just confident in what it does well.
The short rib benedict alone was enough to justify the stop. Rich, satisfying, and the kind of dish you keep thinking about long after the plate is cleared. It was easily one of the food highlights of the trip.
Sailing into the Sunset
That afternoon brought the standout experience of the weekend: a sunset sail with Sail San Diego.
Being out on the water as the light changed was everything we’d hoped it would be—quiet, unhurried, and genuinely memorable. The city looks different from the bay, softened somehow, and the rhythm of the boat made it easy to let the rest of the world fade out for a while. If there was one moment that defined the trip, this was it.
A View Worth Sitting For
We wrapped up the weekend with a late dinner at C Level Lounge. Once again, the table placement wasn’t great. We weren’t seated by the windows, and the setup didn’t feel especially conducive to a relaxed, end-of-trip dinner.
What did ultimately made the stop worthwhile was the view. Lights reflecting off the water, and the sense of being on the harbor did most of the heavy lifting. The food was fine, but without the setting, the experience wouldn’t have stood out.
Sometimes a place earns its reputation for reasons other than what’s on the plate—and in this case, the view was the reason.
San Diego has a way of reminding us why we travel the way we do now. Fewer checklists. More pauses. Better meals when they happen, and the willingness to let a few things miss the mark along the way. This trip wasn’t about doing everything—it was about spending time together, doing a handful of things well, and letting the rest unfold naturally.