Date night in Shelter Island / Harbor Island
Where to eat, drink and end the night in Shelter Island / Harbor Island.
23 spots · Jump to the list
Planning a date night in Shelter Island / Harbor Island? We track 23 spots here — places for dinner, bars and things to do outdoors — and the best-rated of them are below, editors' picks first.
For one kind of night, the Shelter Island / Harbor Island guides plan the whole evening: cocktail bars, restaurants with a view 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 Shelter Island / Harbor Island
Editors' picks first, then by rating.
Bar 1924
5.0(19)Shelter Island / Harbor Island · $$
The Wine Pub & Restaurant
4.9(22)Shelter Island / Harbor Island · $$
Tom Ham’s Lighthouse
4.8(15)Shelter Island / Harbor Island · $$$
Dumpling Bar
4.5(24)Shelter Island / Harbor Island · $$
Point Loma Lighthouse
4.5(22)Shelter Island / Harbor Island · $
Harbor Island Park
4.5(8)Shelter Island / Harbor Island · $
Mitch’s Seafood
4.3(17)Shelter Island / Harbor Island · $
The Bar at Moniker General
4.3(16)Shelter Island / Harbor Island · $$
Stone Brewing
4.3(4)Shelter Island / Harbor Island · $$
Ketch Grill and Taps
4.2(26)Shelter Island / Harbor Island · $$
Jimmy's Famous American Tavern in Point Loma
4.2(24)Shelter Island / Harbor Island · $$
Old Venice Restaurant
4.2(22)Shelter Island / Harbor Island · $$
Pearl Hotel
4.2(15)Shelter Island / Harbor Island · $$
Mess Hall
4.1(25)Shelter Island / Harbor Island · $$
Bali Hai Restaurant
4.1(21)Shelter Island / Harbor Island · $$$
Blue Wave Bar & Grill
4.0(23)Shelter Island / Harbor Island · $$
Pinot’s Palette
Shelter Island / Harbor Island · $$
Humphreys
Shelter Island / Harbor Island · $$$
Cabrillo National Monument
Shelter Island / Harbor Island · $
Next Level Sailing
Shelter Island / Harbor Island · $$$
Sail San Diego
Shelter Island / Harbor Island · $$$
Pomodoro Ristorante Italiano
Shelter Island / Harbor Island · $$$
Carruth Cellars Urban Winegarden & Cheese Shop
Shelter Island / Harbor Island · $
Good to know
- What are the best date spots in Shelter Island / Harbor Island?
- Our top pick is Bar 1924, rated 5.0 out of 5. The Wine Pub & Restaurant and Tom Ham’s Lighthouse are close behind.
- Where should we eat in Shelter Island / Harbor Island?
- Try Tom Ham’s Lighthouse, Dumpling Bar and Mitch’s Seafood for dinner.
- Where can we get a drink in Shelter Island / Harbor Island?
- Try Bar 1924, The Bar at Moniker General and Pearl Hotel for cocktails.
- What's the most romantic spot in Shelter Island / Harbor Island?
- The Wine Pub & Restaurant and Pomodoro Ristorante Italiano are the most romantic on this list.