Little Italy is one of our favorite places to go out to eat and drink! There are tons of good bars and restaurants in this area. Some of the favorites are Ballast Point Brewery, Waterfront Bar & Grill (one of the oldest bars in San Diego), Carruth Wine Cellars, and Crack Shack (amazing chicken sandwiches).
For nightlife, this historic district is in the heart of downtown San Diego. There are restaurants, entertainment, art galleries, and shopping, all within walking distance. Some of my Bri and Matt's favorites are Altitude Sky Lounge, Vin de Sarah and Trailer Park after Dark.