Once upon a time the city streets of Little Italy were home to a thriving fishing community founded by Italian immigrants. It has since evolved into one of the most modern and trendy neighborhoods in San Diego. The lively social scene makes it the perfect place to enjoy both a day and night out on the town.

I've compiled a comprehensive list of the best 45 spots to eat, drink and be merry in Little Italy. From the swanky high brow spots to the cool and comfy, it's all here. Plan a romantic evening with that special someone or invite your pals out for a brunch date. Bookmark this page and consider it your go-to tool for social planning in Little Italy. Don't forget to check out my neighborhood guide to North Park.

Trendy Casual Dinning in Little Italy

Herb & Eatery - Happening hangout for sandwiches, salads & baked goods with communal tables & a gourmet market.

Loading Dock - Mellow joint pairs wine, beer & soju cocktails with eclectic bites plus live shows in the back room.

Super Cocina - El Camino - Buzzy spot offers margaritas & seasonal Mexican grub, plus an outdoor patio, happy hour & DJ nights.

Rakiraki Ramen - Ramen both classic & creative, plus rice bowls, snacks, sake & beer, in casual yet stylish environs.

Pokirrito - Enjoy fresh poke creations including perfectly-packed sushi-burritos.

Grab & Go - Regional chain eatery offering made-to-order sandwiches as well as salads & coffee.

Prep Kitchen - Hip local chain spot draws foodies with seasonal American grub, creative cocktails & happy hour.

Burger Lounge - Modern counter-serve burger spot serving grass-fed beef, free-range turkey & quinoa varieties.

Bar One - Classy sports bar with fido friendly outdoor seating.

Isola Pizza Bar - Sleek, contemporary pizzeria & wine bar slinging inspired Neapolitan-style pies & small plates.

The Crack Shack - Fun spot for chicken & egg dishes with stylish outdoor seating, a full bar & a bocce court.

Best Boutiques in Little Italy

Stroll - Bright & airy boutique carrying bohemian-inspired women's apparel & accessories in a quaint setting.

Vocabulary - Boutique offering contemporary fashions for women & men, plus accessories & some home decor.

Little Apple - Intimate, local boutique featuring fashionable women's clothing & accessories in a modern interior.

Walter & George - Located inside the James Coffee Co. space, this little shop offers trendy home goods and leather accesories.

Crema - Also located inside James Coffee Co. space, this boho trendy boutique is inspired by free spirits. Shop women's aparel and home goods.

Specialty Drinks

James Coffee Co. - Hip local chain doling out coffee & espresso-based beverages crafted from house-roasted beans.

Bottlecraft - A selection of bottles from domestic & international craft breweries, plus a tasting room.

Ballast Point - Brewery & pub providing acclaimed beers, refined bar fare & to-go kegs.

Vino Carta Wine Bar - Casual wine bar & bottle shop offering retail wine sales, wine by the glass & light bites.

Pali Wine Co. - Wine tasting bar with minimalist decor & an upstairs patio serving a variety of vino & charcuterie.

Bolt Brewery - Tasting room for a local brewery serving up craft beer, pizza & bar snacks in industrial digs.

Wine House - A very quaint and special Wine Bar in the heart of Little Italy. Come have a drink prior to your dinner reservation; and why not have a drink after dinner.

Juice Crafters - Juice bar which uses raw gourmet, 100% natural ingredients to prepare some of the most amazing freshly pressed juices.

Italian Restaurants

Barbusa - Stylish Italian restaurant with Pop Art decor & a marble-topped bar serving modern Sicilian fare.

Bencotto - Chic bi-level eatery famed for artisanal Italian eats, including handmade pasta & classic desserts.

Monello - This sleek eatery serves handmade pastas, gourmet pizzas & Italian street food plus weekend brunch.

Civico 1845 - Contemporary Italian cooking with vegan options offered in warm digs with reclaimed wood & a patio.

Brunch Spots

Davanti Enoteca - Rustic-chic hot spot known for its large patio, happy hour & diverse menu of refined Italian eats.

Craft & Commerce - Taxidermy & old books line the walls of this hip gastropub, serving seasonal eats & craft cocktails.

Monello - This sleek eatery serves handmade pastas, gourmet pizzas & Italian street food plus weekend brunch.

Sweet Treats

Pappalecco - Panini, gelato & coffee served in charming digs or on the outdoor patio at this cozy Italian cafe.

Extraordinary Desserts - From coffee cake to crème brûlée, this airy eatery offers a range of desserts, plus savory options.

Solunto Ristorante & Bakery - Italian cafe serving baked goods, pizza, gelato & more in a modern space with colorful mosaic tiles.

Yogurtland - Go with classic frozen yogurt or choose fun fruity flavors like guava and pineapple.

Fancy Date Night Restaurants

Ironside Fish & Oyster Bar - Seafood fare & cocktails offered in a renovated warehouse with quirky, nautical design accents.

Juniper & Ivy - Spacious, modern restaurant serving imaginative New American fare & drinks in woody, arty surrounds.

Herb & Wood - Sprawling, upscale locale serving rustic, wood-fired dishes & old-school cocktails.

Flowers on table inside Herb & Eatery restaurant and shop in Little Italy.

Afternoon Date at Café Gratitude

When news traveled that hip LA chain Café Gratitude opened up a location in San Diego, I immediately made plans to visit. This popular spot offers creative plant-based fare and my favorite kombucha on tap. The modern clean digs set the scene for a perfect cool-chic outing. My boyfriend and I had an late afternoon lunch date.