Around The Cordova Bar
3 stops, all within a short walk
1
0.6 mi
5:30 PMDinner
2
0.6 mi
7:00 PMCocktails
3
8:30 PMSomething sweet
Frost Me Cafe and Bakery
Dessert Shop
555 W Date St, San Diego, CA 92101, USA
Little Italy / Middletown
← Best cocktail bars in San DiegoDate night guide · San Diego
A cocktail night in Little Italy / Middletown
A proper drink between dinner and dessert.
6 spots · Jump to the list
These are bars you go to for the drinks themselves — a considered menu, careful technique, a bartender who can make you something that isn't on it. They sit best in the middle of a night: after dinner, before dessert, or as the nightcap. Restaurants with a strong bar are on the restaurant lists instead.
This guide ranks 6 cocktail bars in Little Italy / Middletown. Editors' picks come first, then the rest by rating, and the plans below build a whole evening around the best of them.
Nights people planned here
Published date nights with a stop on this list.
adventurousStaff Pick
Make a night of it
Routes around the top spots on the list, with the best-rated places nearby for the rest of the evening.
Around Shibuya Nights
3 stops, all within a short walk
1
0.7 mi
5:30 PMDinner
2
0.7 mi
7:00 PMCocktails
3
8:30 PMSomething sweet
Around Kiku Room
3 stops, all within a short walk
1
0.8 mi
5:30 PMDinner
Farmer's Bottega
Restaurant
860 W Washington St, San Diego, CA 92103, United States
Hillcrest / Bankers Hill
4.9
2
0.1 mi
7:00 PMCocktails
3
8:30 PMSomething sweet
Cocktail bars in Little Italy / Middletown
Editors' picks first, then by rating.
The Cordova Bar
4.5(13)Little Italy / Middletown · $$
Shibuya Nights
Little Italy / Middletown · $$
Kiku Room
4.7(18)Little Italy / Middletown
Sunbird
4.0(1)Little Italy / Middletown
Bar
False Idol
Little Italy / Middletown · $$
The Pool House
Little Italy / Middletown · $$
Good to know
- What's the best cocktail bar in Little Italy / Middletown for a date?
- Our top pick is The Cordova Bar, rated 4.5 out of 5. Shibuya Nights and Kiku Room round out the top 3.
- Are there affordable cocktail bars in Little Italy / Middletown?
- Yes — The Cordova Bar, Shibuya Nights and False Idol are all $$ or under.
- What should we do before or after?
- Make it a cocktail night: dinner, then cocktails, then something sweet. The plans on this page pair each top spot with the best-rated places within about a 20-minute walk.