The Perfect Date Night in Little Italy SD

Compared to the more party-like atmosphere of the Gaslamp Quarter, Little Italy is a prime destination for couples out for a romantic date night. Evening in Little Italy will have you walking close together with your date on the narrow sidewalks, peeking into warmly lit restaurants to see what looks good and basking in the warm smells of italian food the kitchen wafting out almost every door. Lit with twinkle lights most of the year, Little Italy encourages a romantic atmosphere in the evening and with the sound of many people speaking Italian, you can almost imagine you are walking the streets of Florence.

Wine Bars

So Diego - Date Night Little Italy

Before starting dinner, you and your date can decompress in one of the many area wine bars. Little Italy has become a wine destination with at least 6 fun and flavorful wine bars on or right off the India St.

Pali Wine: At the north end of Little Italy you will find Pali Wine, just look for the selfie-worthy Fine Wine & Good Times painted building. At Pali Wine you can enjoy your glass of local California wine along with a generous charcuterie board featuring select meats, cheeses and fruits you’re sure to love. Besides the ground-floor tasting room, there is a roof-top patio which beautiful during the day, but particularly excellent in the early evening.

Vino Carta: At Vino Carta selection is heavy on small, family run wineries with sustainable farming practices. They provide a rotating selection of wine by the glass as well as a retail store where bottles can be purchased. On the weekend, tasting flights are available for $15.

M Winehouse: Tucked inside the oldest house in Little Italy, M Winehouse is a cozy spot to sip a glass of wine and watch the bustle of India St. A variety of seating options from cheerful bistro tables in the front, intimate 2-person tables in the back and an upstairs area filled with snug spots and a variety of board games makes this an ideal stop for couples and small groups.


So Diego - Date Night Little Italy

There are so many great dining options in Little Italy so we just picked a few of our favorites. Reservations are recommended especially on the weekends.

Civico 1845: Opened in 2015 by two Italian brothers, this intimate spot is at the corner of India & Fir, right next to the Piazza Basilone with its globe styled fountain. Besides it’s delicious authentic Italian menu, Civico 1845 also includes an additional menu, show-casing a variety of vegan and gluten-free options.

Barbusa: Barbusa for a twist on modern Sicilian cuisine. This striking restaurant has a generous selection Sicilian favorites and modern takes on the classics. Can we recommend the Bolognese al Forno or the Carbonara con Piselli pasta as a dish to share with your date?

Ironside: A departure from the areas Italian options, Ironside is breath of fresh ocean air. From fresh caught oysters to decadent whole lobsters to crunchy fish & chips, there is an option for every seafood-loving palate. Enjoy your meal inside the or on the patio, right in the heart of the very active India St.


So Diego - Date Night Little Italy

A night out would not be complete without dessert and when in Little Italy, gelato is the obvious choice. You can also find cookies, pastries and treats at many of the Italian restaurants.

Pappalecco: Locals agree that Pappalecco has some of the best gelato and most friendly staff in San Diego. Though Pappalecco has grown and now has five locations throughout San Diego, the Little Italy location started it all. Escape the activity on India St and walk just 2 blocks to it’s door. You’ll find a short line even in the evenings as people stop by for coffee, authentic Tuscan pastries and yes, gelato.  

Solunto: Tucked into the Solunto Italian restaurant on India St is a bakery specializing in Italian cookies, gelato and breads. This is a great place to pick of a tray of packaged Italian cookies to enjoy at home or some fresh baked bread for breakfast. Of course, grabbing an assortment of cookies to eat right away is our recommendation.


So Diego - Date Night Little Italy

After dessert, keep the date going with a visit to one of the local bars. Kettner Exchange and Born & Raised have rooftop bars where you can enjoy the lights of Downtown or watch a few flights come in.

Kettner Exchange: Pop into this sophisticated spot and head up to the rooftop patio for prohibition styled cocktails, a generous selection spirits, and a judicious list of curated wines by the glass or bottle.

Born & Raised: The newest addition to Little Italy, this opulent steakhouse includes a rooftop patio with velvet booths and stunning views of Downtown. Inside, the bar boasts rich walnut, Italian marble and brass insets.

If you are interested in a more detailed tour of the wine options in Little Italy, be sure to check out our Vino! Vino! Little Italy Stroll that runs weekly. This tour is a great option for couples. We also have a brewery tour available.

Street parking in Little Italy can be hard to find but there are valet options around different restaurants. Just drive down India St and you will see at least 2 valet options each evening. There are multiple paid parking lots throughout the neighborhood; just a few blocks walk from the main India St strip. Little Italy is also easily accessible from the trolley line with the County Center/Little Italy stop just down the street from the main restaurant area.


Book our Little Italy Pizza Tour today!