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Date night in Little Italy / Middletown
Where to eat, drink and end the night in Little Italy / Middletown.
53 spots · Jump to the list
Planning a date night in Little Italy / Middletown? We track 53 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, special-occasion restaurants, restaurants with a view and dessert spots, each with dinner and a last stop within walking distance.
Nights couples planned here
Published date nights with a stop on this list.
The best date spots in Little Italy / Middletown
Editors' picks first, then by rating · the top 24 of 53.
RestaurantRomanissimo
5.0(22)Little Italy / Middletown · $$$
RestaurantBarra Oliba
4.8(20)Little Italy / Middletown
BarThe Cordova Bar
4.8(13)Little Italy / Middletown · $$
Rooftop & TheaterRooftop Cinema Club Embarcadero
4.8(6)Little Italy / Middletown · $$
MuseumStar of India
4.8(6)Little Italy / Middletown · $
BarShakespeare Pub
4.7(24)Little Italy / Middletown · $
Italian RestaurantGaribaldi
4.7(24)Little Italy / Middletown · $$
BakeryGelato Vero Caffe
4.7(20)Little Italy / Middletown · $
BarAero Club Bar
4.7(17)Little Italy / Middletown · $
GardenHarper’s Topiary Garden
4.7(12)Little Italy / Middletown · $
ParkWaterfront Park
4.7(7)Little Italy / Middletown · $
BreweryBallast Point
4.7(6)Little Italy / Middletown · $$
RestaurantC Level
4.6(26)Little Italy / Middletown · $$
BreweryBallast Point Brewing Little Italy
4.6(19)Little Italy / Middletown
RestaurantAnimae
4.6(19)Little Italy / Middletown · $$$$
CafeJuice Alchemy
4.6(15)Little Italy / Middletown · $
RestaurantAzuki Sushi
4.6(12)Little Italy / Middletown · $$
RestaurantBurgeon at The Arbor
4.6(5)Little Italy / Middletown · $$
RestaurantTop of the Market - San Diego
4.5(21)Little Italy / Middletown · $$$
MarketMona Lisa Market
4.5(20)Little Italy / Middletown · $
RestaurantRoVino Rotisserie + Wine
4.5(16)Little Italy / Middletown · $$
BarWaterfront Bar Tavern
4.5(16)Little Italy / Middletown · $$
RestaurantMona Lisa Italian Foods
4.5(6)Little Italy / Middletown · $$
RestaurantMiguel’s Cocina
4.5(4)Little Italy / Middletown · $$
Good to know
- What are the best date spots in Little Italy / Middletown?
- Our top pick is Romanissimo, rated 5.0 out of 5. Barra Oliba and The Cordova Bar are close behind.
- Where should we eat in Little Italy / Middletown?
- Try Romanissimo, Barra Oliba and Garibaldi 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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