Things to Do in Little Italy, San Diego

Podcast Episode #6 – My guest today who will explain the amazing things to do in Little Italy is AnnMarie Rose who is a brand strategist in San Diego. Although Little Italy is considered to be “downtown”, we usually think of our downtown area to be where all the tall buildings are – near the Gaslamp area. It has a completely different feeling than what I consider “downtown”

What do you love about Little Italy?

I love the energy of the area, clean, super close to the bay. It has the relaxed San Diego vibes but not a touristy area. It is really family friendly.

How is Transportation in Little Italy

If you are staying close to downtown, then don’t even rent a car. Little Italy is very close to the San Diego airport (less than 10 min). Can get an Uber or Lyft for less than $10.

Plan to hang around downtown do a ride share or rent a scooter. They have scooter parking spots. They have widened a lot of lanes to accommodate the scooters.

How do you rent a scooter downtown?

To rent a scooter get an app on your phone for Lime, Bird, etc. Put in your credit card information and you’ll be charged depending on the distance. AnnMarie said it was only $2-3 to get from Little Italy to all the tall buildings in downtown. The most she has paid was about $5.

Can I take a train into Little Italy?

The Coaster stops at Santa Fe Depot on Kettner Blvd. The Coaster is so easy to use. AnnMarie recently took it for the first time from Little Italy to Solana Beach. It was less than 30 min and it was great, fun and pretty. You’ll get some great views of the the ocean. If you don’t want to deal with parking and you’re coming from the north this is really a great mode of transportation.

Where should you park?

Parking is very difficult in Little Italy. Although there are paid lots, they are small and usually full. Paid lots closer to gas lamp then walk or do the scooter. There is a free ride (parking downtown) Free Ride it is like Uber/Lyft with multiple passengers?

Hotels / Places to Stay

AnnMarie says that if you are on a budget you may want stay in Bankers HIll instead of Little Italy. Something to be mindful of if you are a super light sleeper is that planes fly overhead and it can be very loud. Bring earplugs. Check reviews to see if the place your staying is in the flight paths.

It can be more expensive to rent in Little Italy as there are not as many airbnb because of restrictions for owners. You would be able to find a house more easily in Bankers Hill. would be good for bigger families.

Hotel Republic

Sofia – The Sofia is more downtown.

Carte, a Curio Collection hotel – the Carte offers a full array of unique amenities.

Shopping in Little Italy

Shopping – Shopping here is a lots of boutiques without the big box stores. Lots of fashion, home decor and vintage furniture. All the shopping is local owners. There are a few touristy shops.

Farmer’s Market Little Italy is well known for its weekly (every Saturday) farmer’s market. It isn’t just produce, you’ll be able to find all sorts of hot food and other goods throughout the 5 blocks. Live music on nearly every block of the farmer’s market.

Live Music 

Piazza della Famiglia – every Sat night

Music Box– intimate that attracts good names that you hear on the radio. (I’ve included an affiliate link here. You won’t pay any more however I will get paid as an affiliate if you do buy a ticket)

Waterfront Park – Playground – 1600 Pacific Highway, San Diego, CA 92101. great for kids. Relaxing area. Up against the Harbor.

If you want a beach you are only 10 min drive from Coronado or Pacific Beach

Wineries – several tasting rooms

Carruth Cellars Wine Garden – 2215 Kettner Blvd – Carruth is AnnMarie’s favorite place. They have 3 locations in San Diego but this is her favorite because of the garden.

M Winehouse – 1918 India St

Pali Wine Company – 2130 India Street. Pali Wine has a nice roof top setting.


Balast Point – 2215 India Street – Balast Point is San Diego based. Private outdoor cubbies. Full menu.

Bolt Brewing – 1971 India Street- Bolt is always happening. Garage door with a bar on either side of it so it feels open air.

BottleCraft – 2252 India Street. If you want to taste a lot of different beers they have a lot on tap and you can buy bottled beer. She likes Kombucha there since she is gluten intolerant.


Nolita Hall – 2305 India Street. Great place for family or to watch a game. Shuffleboard inside. Awesome salads, pizza, cocktails, beer. Upscale and more than a regular sports bar. majority of the other food is not Italian

Cloak and Petal –1953 India St. Cloak and Pedal is a high end Sushi/fusion restaurant with an urban, yorkie vibe. It is not for children. Cherry trees in the middle of this restaurant.

Crack Shack – 2266 Kettner Blvd. The Crack Shack is all about chicken but not you’re typical chicken. This place is co-owned by Chef Richard Blais (you might remember him from Food Network). AnnMarie says that her husband always says to look at Instagram at the food and pick out what you want based on the pictures not the description. The menu description doesn’t do it justice. This casual place is great for family and is so much fun with lots of games outside.

Café Gratitude – 1980 Kettner Blvd. The first thing they will ask you here is about food intolerances or allergies. Interesting fun place and great meals. Even AnnMarie’s parents who have a midwest palette really like it. The food is Vegan.

Queenstown Public House – – 1557 Columbia St. Queenstown is great for brunch and happy hour


Civico 1845 – This is AnnMarie’s favorite Italian restaurant and she mentioned that it is really authentic. It has a bit of a causal vibe. Note, AnnMarie was so enthusiastic about this place that I went to lunch there less than 30 min after our podcast interview. I had one of the best ravioli dishes I’ve ever had.

Benecotto Italian Kitchen– 750 W Fir St #103 – Benecotto has a more of an upscale vibe. This is my favorite Italian restaurant in the US. However I have to say that Civico 1845’s food gave me the same authentic feeling as when I go to Italy. It is worth going to both places

Bars and Speakeasys

False Idol 675 W Beech St. – The False Idol Speakeasy is Tiki style bar hidden in the back of Craft and Commerce and you have to ask the hostess to get in or get a reservation online. This place almost feels like Rainforest Café but it is more unique. AnnMarie mentioned that it has a waterfall.

Craft and Commerce 675 W Beech St. – Craft and Commerce has a woodsy feeling to it. Taxidermy & old books line the walls of this hip gastropub.

Waterfront Grill 2044 Kettner Blvd. – The Waterfront Grill is the oldest bar in San Diego. This 1933 institution outlasted the waterfront but still draws crowds with pub grub & happy hour.

King and Queen Cantina 1490 Kettner Blvd – King and Queen Cantina has a great Happy Hour. Anne Marie says that this is a hip, airy eatery for updated Mexican fare & cocktails on two art-filled levels with a sidewalk cafe. 

Queenstown Public House 1557 Columbia St – Queenstown is great for breakfast


Extraordinary Desserts – 1430 Union St. Extraordinary Dessert is well known for dessert including gluten free ones. People usually don’t realize that they also serve breakfast, lunch, and dinner.

Pappalecco – 1602 State Street. Pappalecco has fantastic gelato and pastries. Sheri thinks they might have the best almond filled croissants that she has ever had outside of Europe.

Bobboi – AnnMarie is crazy about the gelato at Bobboi. They also have a location in La Jolla.