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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 and spots for dessert — 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.

wine n rooftoppp
romantic
San Diego

J & Tony’s Discount Cured Meats and Negroni Warehouse → Chez Loma → TopSail

3 stops · $$Llexii.afterss
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 49–56 of 56 spots

Good to know

What are the best date spots in Little Italy / Middletown?
Our top pick is Olala Crepes and Sweets. Chocolate Cafe and Kettner Exchange are close behind.
Where should we eat in Little Italy / Middletown?
Try Kettner Exchange and TopSail for dinner.
Where can we get a drink in Little Italy / Middletown?
Try Kettner Exchange, The Pool House and False Idol for cocktails.
Where can we get dessert in Little Italy / Middletown?
Try Olala Crepes and Sweets, Chocolate Cafe and Frost Me Cafe and Bakery for something sweet.

Date night guides for Little Italy / Middletown

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