Staycation in San Diego: Little Italy, Seaport Village, and Jax’s First Trolley Ride

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Written By J.S. Whaldo

Staycation in San Diego means finally taking the time to explore the city we call home. Even after living here for over two years, there are still so many corners we haven’t seen—Little Italy, Seaport Village, even spots we thought we knew already. This summer, we’re riding the trolley, walking the waterfront, discovering new bites, and bringing our dog Jax along for the adventure. If you missed the start of this staycation series, you can catch up here.

Just your average Saturday in San Diego: mermaids, tacos, and sea breezes. / Photo by Whaldo Digital Content

Let the Staycation Continue

San Diego is such a fun city to visit. There’s Old Town, Little Italy, and so much more to explore. I’ve been a resident for over two years now, and I’m just beginning to scratch the surface. Welcome back to my Summer 2025 Staycation series.

It’s still June—which means June Gloom. Trust me, it’s a real thing. Living near the coast, we get the gloom in the mornings and evenings, and some days, it never really burns off. I’m still in leggings and T-shirts most days, usually with a sweatshirt or hoodie nearby. But the cooler weather isn’t keeping us from getting out and enjoying the city.

Trolley to Little Italy: Lunch and Laughs

Recently, we took the trolley down to Little Italy to meet our friend, Ms. Leon, for lunch. I love that we can park for free near home and hop on the trolley to explore so many of San Diego’s neighborhoods. The round-trip fare is cheaper than parking almost anywhere downtown. Sure, free parking exists, but it’s a hunt—and not usually a quick one.

We took the Blue Line trolley to the County Center/Little Italy Station and walked north along Kettner Boulevard. We passed the Little Italy Mercato Farmers’ Market, which is held on Wednesdays and Saturdays. I would have loved to stop, but we had a lunch date waiting for us.

We met Ms. Leon at Postino, a lively spot known for its mix-and-match bruschetta boards, crisp brews, and great wine. We shared a couple of boards, laughed over a bottle of white, and caught up. Ms. Leon even discovered a new favorite wine and bought a bottle to take home—always a bonus when a neighborhood outing turns into a new favorite find.

Wandering Through Italian Flavors

After our meal, we wandered through Little Italy to explore a bit more. We'd only been once before—for my birthday dinner at Herb & Wood (I’m a longtime fan of Chef Brian Malarkey, and couldn’t wait to try it—delicious is an understatement). Postino is right across the street, so this time we walked a block over to India Street and explored southward. We passed Ballast Point Brewing on the corner of Ivy and India and mentally added it to our future outings list.

Little Italy is full of charm, and you can find just about any style of Italian cuisine—from casual trattorias and cozy pizza takeout spots to upscale dining. We popped into The Market by Buon Appetito, an Italian grocery and café. The aroma alone was enough to tempt me, but somehow, I walked out without a single item. That’s a personal record.

Oysters, Aperol, and a Spiritual Stop

Later, we stopped at Vicenzo Cucina and Lounge for a drink and a few oysters—because let’s be honest, you don’t need to be hungry to enjoy a couple of oysters and an Aperol Spritz. We sat outside, people-watched, and just soaked up the atmosphere.

Snack stop at Vicenzo Cucina and Lounge / Photo by Whaldo Digital Content

Before heading home, we wandered into Earth’s Elements, a beautiful little shop. I picked up some white sage and a couple of black tourmaline bracelets before we headed back to the trolley.

Jax’s First Trolley Ride: Onward to the Embarcadero

A few days later, we ventured out again—this time to Seaport Village, with Jax in tow. It was his first time on the trolley. He’s a great traveler, but this ride was a little noisy, especially being down at his level near the doors. We had to switch from the Blue Line to the Green Line, but he handled it like a champ. He was eager to board the second train—such a brave boy.

Surprises Along the Waterfront

We got off at Santa Fe Station so we could walk along the Embarcadero and pass by the USS Midway Museum on our way to Seaport Village. We took a detour into Tuna Wharf, where we found the Embracing Peace statue—also known as the Kissing Statue, a replica of the famous WWII photo of a sailor kissing a nurse. We’d seen a similar one in Civitavecchia, so it was fun to stumble upon San Diego’s version.

Nearby, we discovered the National Salute to Bob Hope and the Military. I had no idea this tribute existed, and it’s powerful. It includes a loop of Bob Hope’s classic USO jokes, which adds to the emotional impact.

The Embracing Peace statue and Tribute to Bob Hope / Photos by Whaldo Digital Content

A “Daycation” Celebration at Seaport Village

We continued our walk, passing the USS San Diego Memorial and vendors selling handmade goods, and eventually arrived at Seaport Village, which was hosting a community event: the Daycation Celebration. There were entertainers, free samples from restaurants (the hummus from Malibu Farm San Diego was my favorite), and even free carousel rides. We wandered through the booths, caught glimpses of sea lions bobbing near the fishing boats, and enjoyed the festive atmosphere.

Park Play and a Pint Before Home

Next to the village is Embarcadero Marina Park North, where we watched skilled kite flyers make their moves in the breeze. The park was alive with families, picnics, and music—it felt like summer, even under the gloomy sky.

J.S. Whaldo playing on a photo prop, while Jax is wondering why he’s on this thing. / Photo by Whaldo Digital Content

Before heading back, we stopped into Mike Hess Brewing for a cold drink and a little rest. Then it was back on the trolley and home again. Jax did better on the return trip, though he’s still a little unsure. We’ll try again soon—and next time, we’ll pick a seat farther from the doors.

There’s Still So Much to Explore

Part of vacationing in San Diego is venturing out to its many neighborhoods and just… wandering. There’s more we want to see. There’s something special about going somewhere with no set plan and finding a new favorite spot—or a statue you didn’t know existed.

Who knows what we’ll find next in Barrio Logan, Hillcrest, East Village, or any of San Diego’s other unique communities?

It’s shaping up to be a great summer.

—J.S. Whaldo

Practical Travel Notes: Exploring San Diego Like a Local

June Gloom is real.
If you’re visiting in early summer, be prepared for overcast skies—especially in the mornings and evenings. It’s still plenty comfortable for exploring, but bring a sweatshirt or light jacket for those cooler coastal moments.

Where to Stay:
If you’re staying downtown, you’ll be close to everything we explored in this post. A few convenient, walkable options:

Eats and drinks we loved:

Don’t miss:

Local Tip: Dog tips
Dogs are allowed on trolleys, but it may take them a ride or two to get used to the noise—especially near the doors. Jax handled it like a champ (mostly). Parks near Seaport Village, like Embarcadero Marina Park North, are ideal for a break and some kite-watching.

Local Tip: Getting around San Diego without a car is surprisingly easy.
The trolley system is affordable, clean, and runs to many popular destinations, including Little Italy, the Gaslamp Quarter, and the Embarcadero. Parking near trolley stations (like the one we use at the Tecolote station) is often free—making this a stress-free alternative to downtown parking.

J.S. Whaldo
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