I’ve been to both Bencotto and Monello, but not since before Covid. I like them both but prefer Monello. The interior ambiance at both restaurants is actually quite nice, Monello is just a bit more relaxed. They are literally right around the corner from each other, the entrances are only about 50 feet apart +/-
Born & Raised is probably the most upscale of the restos in LI. The interior is fancy. If you like red meat this is your place. Not a lot of options for vegetarians. I’ve had both dinner and drinks and apps there. I thought the food was very good, the steaks excellent and the drinks even better. It’s not Manhattan weather for me, but they have a drink trolley from which they do tableside Manhattans. It’s fun and the drink is a very good rendition. The drinks from the bar are equally as good. I’ve tried to do Happy Hour on their rooftop bar but there has never been available seating so we’ve always ended up having to go back downstairs to the bar.
Ironside is very good for fish and seafood altho’, for me, it gets a bit too noisy. What they do, they do well.
Some options that haven’t been mentioned yet:
Craft & Commerce - it reinvented itself shortly be Covid from a burgers and craft beer joint into a much more serious restaurant, meaning a more creative and upscale menu. (Unfortunately, you’ll have to look for the TINY word menu to view it)
Civico 1845 - is one of the top Italian restaurants in Little Italy, better than Bencotto or Monello. It features the cooking of Calabria, the toe of the boot. My Italian friends give it all thumbs and fingers up. In fact, I’m going to their sister restaurant on Bankers Hill tomorrow night for my B-day.
Kettner Exchange - does creative cocktails and creative food.
Juniper & Ivy has a new chef, one with Michelin credentials. I haven’t been in quite a while and definitely not since the new chef started. I like J&I but it’s always been VERY noisy and I’m not big on having to yell, or at least speak very loudly, in order to have dinner conversation.
I should note that Born & Raised, Ironside, Craft & Commerce along with quite a few other SD restaurants are all owned and operated by Consortium Holdings. All of their properties and holdings are very well done and cosistent from design, to menu, to service. They pay attention to detail and aren’t afraid to spend the money needed to create a good dining experience. The webpages for their places, however, are maddeningly awful and provide very little usable information.
And I should also note…India St., the main drag through LI, has been closed due to Covid and is currently a pedestrian promenade wth most restaurants providing outdoor dining areas. Parking sucks (Uber/Lyft or the trolley). And you will definitely need reservations wherever you decide to go.
If you really want Italian, Cesarina in Point Loma is your best bet. It’s really good and the staff and service warm and well trained. (Yes, their website intro is annoying)
If I was looking to do "must-try"in San Diego it wouldn’t be in Little Italy. My choice would be either Fort Oak or Trust
Good luck, I’m sure you’ll end up with something fun and delicious.