Updated April 27, 2023

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. So, read on for some of our favorite date ideas in San Diego.

WINE BARS

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 for your date night.

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 is 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. This is one of the San Diego attractions that 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

Drinking good wine is always a great date idea for Valentine’s Day. So, if you ever visit San Diego, be sure to try visiting this place. 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 date idea for couples and small groups.

DINNER

A list of San Diego date ideas is never complete without dinner. 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 in Southern California is at the corner of India & Fir, right next to the Piazza Basilone with its globe styled fountain. Besides its delicious authentic Italian menu, Civico 1845 also includes an additional menu, showcasing a variety of vegan and gluten-free options.

Barbusa

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

Ironside

A departure from the area’s Italian options, Ironside is a 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.

DESSERT

A night out in San Diego county 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 in the area.

Pappalecco

Every San Diegan agrees 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 its 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 the perfect place to pick a tray of packaged Italian cookies to enjoy at home or some freshly baked bread for breakfast. Of course, grabbing an assortment of cookies to eat right away is our recommendation.

BARS

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 best cocktails in San Diego and the lights of Downtown San Diego or watch a few flights come in.

Kettner Exchange

Pop into this perfect spot in Southern California and head up to the rooftop patio for prohibition style cocktails, a generous selection of 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 San Diego. Inside, the bar boasts rich walnut, Italian marble, and brass inserts.

Coco Maya

Inspired by exploring the history of the Islands and Latin American regions of the Caribbean Ocean.

The dishes presented by Caco Maya are a contemporary link from the past to the present using local produce and Seafood guided by the Monterey Bay Aquarium Seafood Watch. Culinary flavors influenced by European cooking techniques are echoed throughout the menu with the core of the kitchen coming from the Coal Fired Josper Oven. Hints of the Ocean, smoke, and char will reverberate through all the dishes.

A daily Brunch Menu is centered around composed Latin American and Caribbean breakfast dishes with rotating pastries and a unique Sandwich called Bokit (a stuffed fry bread from the French Islands of Guadeloupe).

Camino Riviera

This Tulum, Mexico-inspired restaurant and bar features a gorgeous interior décor which combines bamboo, macrame, and tropical plants to create a beachy Caribbean vibe. The back bar features tile and stone, and likewise feels like you were transported to the courtyard of a Riviera Maya hotel.

Camino Riviera creates the perfect atmosphere to enjoy one of their fresh cócteles. Drink selection includes but not limited to Passionfruit Spritz, and Motorolo made with Mezcal, Charanda Rum, Nocino Walnut, Cafe Liqueur, and Orange Bitters.

Climb aboard,  you’re in for a ride with our next bar of interest. Wolfie’s carousel bar encapsulates a fun whimsical playland which features hand-carved carousels. Enjoy a fresh glass of their Whispering Angel Rosé while feeling like you have been swept away to a French carnival. 

Wolfie’s Carousel is a singular setting to enjoy a moveable feast with the vanguard of old and new.

You and your date will surely enjoy several of our San Diego food tours. 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 have a Little Italy food tour where you can experience the best bites in the Little Italy neighborhood. If you’re looking for more date night inspiration without breaking the bank, check out our guide with cheap date ideas in San Diego.

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.

Written by:

This blog was written by Aleezah Davenport. Aleezah is a native San Diegan, and a second-generation PLNU alumna. She enjoys exploring the city and taking her girls out for dinner on the cliffs at Sunset Cliffs. Writing about San Diego provides her the opportunity to learn more about the local scene, and share her newfound knowledge about her hometown – two of the things she loves most. She enjoys sharing her passions with readers, and is excited to be writing for a platform that provides fun information to a large audience.

xxx