Destination | Little Italy

Right beside downtown is one of our favorite, bustling neighborhoods in San Diego. It’s progressive yet has that element of history that makes it extra special. Generations of Italian families made their living here, in Little Italy which was once a thriving tuna fishing industry in the 1920’s. San Diego’s oldest neighborhood business district is still just as lively, with street filled patio cafés, dynamic restaurants, craft brew stops, urban wineries, art galleries, shops and boutique hotels. Some of the most picturesque views of the San Diego bay can be seen in the hills of Little Italy.

Every Saturday, several blocks of Little Italy are shut down for the weekly Little Italy Mercato — believe us, a must visit. Hands down, the best Farmers Market in the city. Locals shop for fresh produce along with gourmet goods, crafts and ready made foods.  It’s reliable (rain or shine), it’s organized, and it’s always delicious. I never leave without a bouquet of beautiful flowers, and fresh salsa, guacamole and chips to bring home for that weekends festivities.

When I was 21, I lived in Little Italy for a year. It was nothing short of amazing and this was back when most of my favorite spots, didn’t even exist yet. Over the past decade, Little Italy has completely blossomed. Cutting edge restaurants seem to always be making a home there, condos popping up everywhere, and a plethora of new shops seem to have appeared every time I visit.

When I lived there my building was adjacent to the famous Extraordinary Desserts and boyyyy is it. Everyday my route home passed the front display window. The most delectable, beautiful cakes and pastries adorned with flecks of gold and fresh flowers. Everything is edible which makes this particular spot, extra special. After living there for a year, I would literally have to shield the side of my face to keep my head from wondering.


Above all, the food is what brings us here. Within the past decade, a slew of luminary chefs have gravitated to Kettner Boulevard, AKA “Top Chef Alley” with countless distinctive eateries in the heart of Little Italy. There is Italian food, but one of the best things about the offerings in this neighborhood is that there is plethora of cuisine, amazing cuisine might we add, to choose from.

Born & Raised has definitely been our go to spot since it recently opened in the heart of the neighborhood. We have been there twice this month alone and it will never disappoint. The interior design is impeccable! Every details, detail was very well thought out, even down to the bathroom design. The vibe is roaring 20’s chic (think Titanic) with a hint of 90’s gangster flair. There are table-side cocktails and salads along with a fabulous rolling dessert cart. Their dry aged meat selections are out of this world. If you don’t believe me, see the image above ↑ Chef Jason McLeod and his crew won’t let you down, you definitely need a reservation so click HERE now to experience the yumminess.

(Local Tip: If downstairs dining is booked, you can always stop by for a cocktail and appetizer on the upstairs deck – beautiful views from up there! A must see)

Chef Jason McLeod


One of our favorite details 😉



It would be hard to put a complete list of places to visit in Little Italy because surely you would end up forgetting something incredible. Here are some tried and true places that will never let you down.

Eats & Drinks

Filippi’s Pizza Grotto – Family style old Italian pizza, casual, family friendly

Born & Raised – Amazing food, fabulous meats and table-side craft cocktails *

Kettner Exchange – Food, Cocktails, Night Out on the Town *

Juniper & Ivy – Date night, amazing food, cool atmosphere

The Crack Shack – Family friendly outdoor good, home cookin’, soul food *

Herb & Wood – Great date night spot or cocktail meetup *

Davanti Enoteca – Italian in a rustic setting (get the cheese and honeycomb focaccia!)

The Waterfront Bar and Grill – 1933 old school local bar

Extraordinary Desserts – Decadent, rich, beautifully crafted desserts and beverages

(*personal fav’s)


Little Apple

Azzurra Capri

Love & Aesthetics

Other Fun Places

Architectural Salvage – Old fixtures and unique home treasures

Farmers Market – Every Saturday (rain or shine) 8am-2pm

1805 Gallery – Open Artist Studio and Exhibition Space

Adelman Fine Art – Contemporary Fine Art Gallery


If you want to get the biggest bang for your buck visit to get up to date information on shopping, dining, and upcoming events!


Love – Whether you are exploring some place near or far you are opening your mind and your heart to all the possibilities the world has to offer. Travel is all about the journey, not the destination. Find a new neighborhood in your area and let your heart wander. 


Ciao Bella,

Katy & Shawna



Miranda McDonald Photography 

Kyla Stuart Makeup


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