Exploring San Diego’s Little Italy

Founded in the 1920s, San Diego’s Little Italy was once home to 6,000 Italian families who built the neighborhood on the back of the tuna fishing industry. Today, it is Downtown San Diego’s oldest neighborhood and a thriving social scene encompassing vibrant restaurants, boutiques, art-design shops, and a variety of historical tales.

San Diego is a city composed of pocket-sized neighborhoods, more so than most of the country’s urban areas and to a point that such a mosaic of communities lends the city its distinct hometown feel. Each neighborhood boasts a unique vibe, and Little Italy is no exception, though it is exceptional—particularly when considering that Little Italy communities around the country have generally declined while San Diego’s has blossomed into a colorful destination.

While in town, the majority of visitors (and locals) tend toward walking along India Street, a north-south commercial corridor running through the heart of the community and boasting seemingly endless restaurants and cafés. This street is strewn with sidewalk cafés and two-top tables under wide umbrellas, where locals of Italian descent can often be found chatting in their native language.

Though India Street is a must, one can also explore the 48-block footprint of this neighborhood via the One-Mile Walk. This self-guided path, marked by plaques at every eighth of a mile, begins at the intersection of Union and Ash and takes walkers through the more residential areas of town before ultimately guiding them back into the heart of the action at popular Piazza Basilone.

In Italy, piazzas are public spaces—traditionally city squares—used as community gathering places. Little Italy’s Piazza Basilone is often the gathering place for families, veterans, and others passing through. Established in 2003, this central space is dedicated to Gunnery Sergeant John Basilone and “the boys that never came home” during the wars of the 20th century. It is the location of many special events (including Little Italy’s annual Tree Lighting and Christmas Village) and its central fountain is a prime photo opp for visitors.

To dive further into the neighborhood’s history, visit The Convivio Center and Little Italy Heritage Museum, where light is shed on the area’s Italian influence through artistic and cultural displays and information. Close by, the San Diego Firehouse Museum is another history-filled spot showcasing firefighting memorabilia dating back 100 years.

A few other musts: Check out the Little Italy Landmark Sign constructed mid-way down India Street; keep an eye out for celebratory banners commemorating famous Italian Americans and families who made Little Italy what it is; and visit Amici Park to watch locals participate in bocce ball tournaments (or try your own hand at this traditionally Italian game with Little Italy Tours).

A first item of importance upon arrival in Little Italy: lodging. Hotels are rampant in Downtown San Diego but a bit fewer and farther between in Little Italy. Consider this lack of blatant tourism part of its beauty. For the most central location, La Pensione Hotel is a prime choice. Rooms are a minimalist white with modern silver touches, and securing a spot on a higher floor may just grant you a balcony overlooking lively India Street below.

Also on site is an indoor courtyard created for lounging and an intimate lobby complete with fireplace; conveniently, the hotel also connects to Caffé Italia, a popular place for morning coffee and cannoli, as evidenced by the throngs of locals who line up each morning for their bit of caffeine. Take it from a local: The wait is worth it.

San Diego’s foodie set ventures out to Little Italy on a regular basis, often to shop and socialize during Saturday’s massively popular Little Italy Mercato, a pop-up farmer’s market with more than 150 booths of artisan foods and locally farmed produce. Beyond this, locals and visitors enjoy Little Italy’s large collection of restaurants, a mix of traditional Italian staples and a new crop of modern eateries.

Ask San Diegans where they prefer to eat and chances are their favorite spots will be in Little Italy. Longtime favorite Buon Appetito is a solid choice for a traditional Italian meal. The dimly lit restaurant buzzes with the chatter of locals and out-of-towners enjoying decidedly rustic fare. In fact, back at La Pensione Hotel, the front desk staff brought Buon Appetito up as a top choice before I’d even shared that I already had reservations here. The reasons why are apparent, as this is not your uber-Americanized spaghetti and meatballs; this is Italian done right.

Take the time to break from the barrage of Italian cuisine and taste California’s fully blossomed farm-to-table movement, a revolution practiced by several area restaurants that support increasingly sustainable and locally sourced practices. One of the better-known spots included in this category is Prepkitchen, a modern eatery specializing in seasonal Californian cuisine (and occasionally reflecting San Diego’s proximity to the Mexican border, should you opt for a dish such as the chilaquiles—a brunch staple throughout San Diego and a Prepkitchen favorite). The restaurant is also known for its cocktail program and bar scene, so stopping by during evening hours is just as appropriate as swinging in for a midday bite.

For those who jump right to dessert, Extraordinary Desserts is a mecca of inspired gourmet sweets, panini, and more served alongside eclectic wines, organic coffees, and special tea blends. Bonus tip: Extraordinary Desserts is located at the starting point of Little Italy’s One-Mile Walk, meaning that slice of Balboa Centennial Cake can be at least somewhat worked off during a post-dessert trek around town.

And of course, there is pizza. Isola Pizza Bar is a modern space for enjoying your favorite pies in conjunction with an extensive wine list and happy hour specials such as farinata (crispy garbanzo beans in the shape of French fries, served with a truffle aioli) and bruschetta burrata & carciofini (bruschetta topped with artichokes, lemon aioli, capers, prosciutto, and fresh burrata cheese). The staff here is also some of the warmest in town, or perhaps it just seems that way once charmed by their Italian accents.

Travelers could spend the duration of their trip eating and still not visit every restaurant Little Italy offers; culinary focus aside, the neighborhood also boasts plenty of opportunities to shop. Boutiques are found along the main and side streets, with one area aptly dubbed “The Cottages” for its string of stand-alone wooden structures that house gems including Love & Aesthetics, a collection of unusual décor and gifts, and Azzurra Capri Boutique, where guests can create their own one-of-a-kind Italian leather sandals decorated with Swarovski crystals.

Art lovers are also bound to discover a few treasures amidst a dozen or so art galleries (the small but whimsical Pecoff Studios by local artist Grant Pecoff is a favorite), and each April Little Italy hosts the Mission Federal ArtWalk, a 17-block free art and music festival that attracts thousands of attendees and features artwork from countless local and imported artists.

For those interested in appearance, a visit to Salotto Blow Dry Bar is a welcoming primping experience. Owner Corrine has decorated the salon to feel like a posh living room, hence the name Salotto, an Italian term that translates to “sitting room.” Salotto exudes the warmth of a home, simultaneously bypassing the more whitewashed, sterile feel that many styling bars convey. On its first floor, a round table allows girlfriends-on-the-go to sit across from one another as they have their hair styled and, if they choose, sip cocktails from the adjacent Porto Vista Hotel.

While San Diego is a year-round destination due to its warm-weather climate, visitors may opt to plan their trip around one of Little Italy’s many annual community events. While art lovers may journey here to experience the aforementioned ArtWalk during April, foodies can try many restaurants in one visit by staying during the Taste of Little Italy. From the Little Italy FESTA! to Ferragosto, both celebrations of Italian culture, something always seems to be happening in these streets. For more information about Little Italy San Diego and to view a calendar of trip-worthy events, visit the Little Italy Association website.