Travelzoo had some interesting information about San Diego’s Little Italy. It has increasingly become one of my favorite places in the city. Let’s see why. I think you will be pleasantly surprised. The Saturday street market is one of my favorite events here. But any day is a good day here.
Thanks to waves of Sicilian and Ligurian immigrants who began building up San Diego’s tuna fishing industry in the 19th century, Italian culture figures prominently into the local mix, too. And as you might guess, Little Italy is the best place to find the vestiges. But as you might not guess, it’s also one of the best places to go for ground-breaking, news-making cuisine—plus some of the chicest décor and design shops in town.


For a quick historic overview, check out a few of the longstanding fixtures—from Our Lady of the Rosary Catholic Church (the nearly century-old spiritual heart of the neighborhood) to the Waterfront Bar and Grill (said to be the city’s oldest continually operating tavern, where Italian fishermen would relax after mending their nets outside the front door) to Mona Lisa Italian Foods (the old-school, family-run deli and restaurant whose sandwiches and slices are legendary).
You’ll also want to check out a few modern nods to the neighborhood’s Italian heritage: Piazza della Famiglia (a 10,000-square-foot plaza where you can enjoy takeout treats from the new Little Italy Food Hall), the more intimately scaled Piazza Basilone (a tribute to WWII Medal of Honor Recipient Gunnery Sergeant John Basilone); and—on Saturdays—the Little Italy Mercato (a vibrant, open-air market).
But you’ve got to show up prepared for at least two meals: ideally, an old-school Italian lunch, followed by a long promenade—this would be the time to work in a visit to the chic Kettner Arts & Design District—and topped off with dinner at one of the city’s buzziest modern restaurants. These include Juniper & Ivy, Herb & Wood, Ironside Fish & Oyster (noticing a theme?).
In keeping with the alfresco theme (because every restaurant we’ve mentioned offers some version of it), wine lovers should make time to pull up a seat outside M Winehouse—a beloved wine bar that occupies the neighborhood’s oldest house: a tiny Victorian beauty that dates to 1888 and makes for the perfect place to toast to your neighborhood discoveries.

I love what the Little Italy Association says: “Our business district is rooted in the toil of immigrants and the perseverance and optimism of a new group of business owners. The strength of their faith and our proximity to the waterfront is what has supported families in Little Italy for generations.”
The city streetcar passes within a block or two of Little Italy. Parking is rather difficult unless you are willing to pay. My suggestion is to go for lunch, when it is less crowded. The area is clean and safe. You will find some rather eclectic dishes. I am still not sure about combining sushi with burritos. Just remember, you can always go to the beach!
Every Saturday, from 8am to 2pm, the Little Italy Mercato takes over four blocks (West Date Street) in the neighborhood. Over 85 vendors participate. Of interest to me are the food vendors, as well as the fresh fruit vendors. They even have a dog park!
I am here Tuesday to Thursday, so no Little Italy Street Market on this trip. But I get to see a long time, dear friend, see a few ballgames, and enjoy the beautiful San Diego weather.