Little Italy San Diego Spontaneous Weekend

Posted on March 20, 2015


Spontaneous vacations are the best kind since there is no agonizing about planning all the travel details and schedule. A Thursday night phone call from a friend, “the condo in Little Italy is in between renters, want to go for the weekend?”, meant our clear weekend was now filled with unplanned fun.

Little Italy Sign

With a warm weather forecast and no dinner reservations, we quickly packed and drove 30 minutes down the freeway to our “Staycation” destination of San Diego’s Little Italy. While I’ve been to dinner here before, I’ve never stayed longer than a few hours. After dropping off our weekend bag at the condo, we headed out in search of food, expecting to find a new Italian restaurant to try. We walked up and down Little Italy’s main drag India Street and decided upon the most bustling restaurant Ironside Fish and Oyster Bar.

Little Italy Ironside inside 1

Turns out you need reservations to eat at a recently opened hot spot, so we booked for Saturday night at the “chefs table”.  Still hungry, we put our name on the list next door at Prep Kitchen – at least we could get in on a Friday night with no reservation. They took my cell phone number to text me when the table was ready – 45 minute wait. We ventured up and down India Street until my cell phone buzzed.

Little Italy Prep Kitchen Wine WallLittle Italy Prepkitchen sign

Prep Kitchen in Little Italy is the younger partier of the trio of restaurants (there is one in Del Mar and La Jolla as well). The vibe was urban, menu eclectic, and service friendly – it felt like we were in the “in” place immediately. The waitress was kind enough to define a few of the items on the menu for us – like the Sauteed Rapini and Sauce Chermoula which is paired with the Pan Roasted Yellowtail with Blood Orange Braised Carrots $27.95. I had the delicious roasted beet and spinach salad $13.50. We raved with our dining neighbors about how the dinner was well worth the wait, how glad we were to have saved room for dessert!

Little Italy Prep Kitchen Yellowtail Little Italy Prep Kitchen Beet Salad

Not quite ready to go “home” after dinner we stopped off at Isola Pizza Bar which made us feel like we were in a small European bar. We started at the bar and moved outside to the back patio for deep conversation solving all the world’s problems.

Little Italy Isola chalkboard Little Italy Isola mural

The next morning, with no plan, we created a mission of shopping for a few things for the condo like water, toothpaste, and toilet paper. Yelp led us on a trek away from Little Italy into true downtown San Diego to a grocery store that no longer exists. Our walk gave us suburbanites  a taste of big city life complete with trash smells and homeless people sleeping in whatever cubbyhole they can find. A Google search helped us backtrack to a 7-11 in Little Italy and lucky for my boyfriend he spotted Little Italy Tobacco shop next door where he replenished his stock of cigars.

Enough of the boring shopping, off we went to the Mercato for some vacation souvenirs. I settled on California Olive Oil and Seed Salts.

Little Italy Souviners

American dinner last night, seafood dinner planned for tonight, we felt the need to have some Italian food while here in Little Italy. No lack of pizza places and Italian restaurants to choose from we decided on Flippis – an icon in San Diego Little Italy and far to busy to get into on a weekend night.

Flippin Pizza Chianti Flippin PizzaLittle Italy Flippis

Delicious pizza + Chianti at lunch = nap time in the afternoon.

Next up was our only “planned” event of the weekend – Saturday dinner reservations at Ironside Fish and Oyster Bar. We headed out two hours early so we could have a before dinner drink. After walking into and out of the VERY busy Craft and Commerce we found quieter Enoteca for some pre-dinner wine tasting.

At Ironside, with our reservation, we were seated in about 10 minutes. Turns out the “chef’s table” is really the chef’s counter where we get to watch busy chefs at work in a kitchen alcove in front of the big kitchen.  We were intrigued by the “quality control guys” inspecting all the plates before shouting out to wait staff to pick up their orders – if they passed inspection. We asked “who are those guys”.  They are Ironside sous chef’s Jose “JOJO” Ruiz and Josh Maynard and Head Honcho Jason McLeod a two-star Michelin Chef, top dog in the kitchen and the quality control patrol.

LIttle Italy Ironsides Chefs

Jose “JOJO” Ruiz and Josh Maynard

Little Italy Quality Control

Ironside Quality Control Chefs

Little Italy Ironside Simple Fish

Simple Fish Mahi Mahi

Little Italy Ironside

Ironside counter dining

Little Italy Ironside decor

Ironside “ship” decor

Little Italy Ironside lobster


The menu is printed daily, and is packed with fresh fish and seafood choices. If you are a red meat person, go somewhere else. I passed on the whole grilled sheepshead fish ($25) with the head still intact that was “exceptionally tender and delicious” according to our counter neighbors visiting from Newport Beach. Instead I ordered the 1 1/2 lb.  lobster ($36) and it was the best lobster I’ve ever had – better even than the one I had in Portland Maine. My date had the Mahi Mahi “Simple Fish” $17.00

It’s clear that historic Little Italy is an up and coming melting pot hot spot not just for Italian food anymore.