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.
The best date spots in Little Italy / Middletown
Editors' picks first, then by rating.
Top of the Market - San Diego
4.2(21)Little Italy / Middletown · $$$
RoVino Rotisserie + Wine
4.2(16)Little Italy / Middletown · $$
Michi Michi
4.1(21)Little Italy / Middletown · $
Mimmo’s Italian Village
4.1(15)Little Italy / Middletown
Underbelly
4.1(13)Little Italy / Middletown · $$
Landini’s Pizzeria
4.1(9)Little Italy / Middletown · $
Allegro
4.0(21)Little Italy / Middletown
Lionfish Modern Coastal Cuisine
4.0(4)Little Italy / Middletown · $$$$
Lala
3.9(22)Little Italy / Middletown · $$$
Glass Door
3.8(9)Little Italy / Middletown · $$
Sugarfish
3.7(9)Little Italy / Middletown · $$
Canvas Cafe & Lounge
3.0(1)Little Italy / Middletown · $$
Maritime Museum of San Diego
Little Italy / Middletown · $$
USS Midway Ship and Museum
Little Italy / Middletown · $$
The Brigantine
Little Italy / Middletown
Herb and Wood
Little Italy / Middletown
Spruce Street Suspension Bridge
Little Italy / Middletown · $
Maranello
Little Italy / Middletown
Shibuya Nights
Little Italy / Middletown · $$
Café Madeleine
Little Italy / Middletown · $
Kiku Room
4.7(18)Little Italy / Middletown
Sunbird
4.0(1)Little Italy / Middletown
Three Three Seven
Little Italy / Middletown · $$$$
Music Box
Little Italy / Middletown · $$
Showing 25–48 of 56 spots
Good to know
- What are the best date spots in Little Italy / Middletown?
- Our top pick is Top of the Market - San Diego, rated 4.2 out of 5. RoVino Rotisserie + Wine and Michi Michi are close behind.
- Where should we eat in Little Italy / Middletown?
- Try Top of the Market - San Diego, RoVino Rotisserie + Wine and Mimmo’s Italian Village for dinner.
- Where can we get a drink in Little Italy / Middletown?
- Try Lala, Canvas Cafe & Lounge and Shibuya Nights for cocktails.
- Where can we get dessert in Little Italy / Middletown?
- Try Michi Michi for something sweet.
- What's the most romantic spot in Little Italy / Middletown?
- Glass Door and Café Madeleine are the most romantic on this list.