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Date night in Little Italy / Middletown

Where to eat, drink and end the night in Little Italy / Middletown.

56 spots · Jump to the list

Planning a date night in Little Italy / Middletown? We track 56 spots here — places for dinner, bars, spots for dessert and things to do outdoors — and the best-rated of them are below, editors' picks first.

For one kind of night, the Little Italy / Middletown guides plan the whole evening: rooftop bars, cocktail bars, live music venues, special-occasion restaurants, restaurants with a view, dessert spots and activities, each with dinner and a last stop within walking distance.

Nights people planned here

Published date nights with a stop on this list.

Fun &  Mediterranean
adventurousStaff Pick
San Diego

K1 Speed → Truva → The Cordova Bar

3 stops · $$ · 1 saveLoloLolo
Bacari North Park → Vino Carta
cozy
Borrego Rooftop → Romanissimo → TopSail
upscale
San Diego

Romanissimo → TopSail

2 stops · $$$$ · 4hCWClaire W.

The best date spots in Little Italy / Middletown

Editors' picks first, then by rating.

Showing 1–24 of 56 spots

Good to know

What are the best date spots in Little Italy / Middletown?
Our top pick is Harper’s Topiary Garden, rated 5.0 out of 5. Ballast Point Brewing Little Italy and Animae are close behind.
Where should we eat in Little Italy / Middletown?
Try Animae, Azuki Sushi and Mona Lisa Market for dinner.
Where can we get a drink in Little Italy / Middletown?
Try Romanissimo and The Cordova Bar for cocktails.
Where can we get dessert in Little Italy / Middletown?
Try Gelato Vero Caffe for something sweet.
What's the most romantic spot in Little Italy / Middletown?
Ballast Point Brewing Little Italy and Juice Alchemy are the most romantic on this list.

Date night guides for Little Italy / Middletown

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