The Five On It • San Diego Date Night

Five unforgettable San Diego date nights.

Imagine finishing work on Friday, already knowing exactly where you're going. The reservation is booked. Dinner is decided. The after-spot is waiting. Just show up and enjoy the night.

Get instant access, $5 Instant digital access. Yours forever.
Full itineraryMaps for every stopInsider tipsBackups & budget options
What's inside

Five date nights, planned down to the minute

Every one runs start to finish, the spots, the timing, the order to do them in, plus reservations, maps, budgets, and a backup for each.

01
The Romantic SplurgeWaves crashing, candlelight, and a view you won't forget.
02
The Cool & MoodySpeakeasy energy, live jazz, and a movie under the stars.
03
The Adventure DateSan Diego Bay at sunset, from the water. Need we say more.
04
The Rooftop CrawlDinner with a 360-degree skyline view, then cocktails even higher up.
05
The Outdoorsy DateGolden hour over the Pacific, then dinner with sandy feet.
Night one · a first taste
7:00 PM
The Marine Room La Jolla

One of San Diego's most iconic dining experiences. Floor-to-ceiling windows sit inches from the ocean, on high-tide nights, waves literally crash against the glass while you eat.

a short drive between the two
9:30 PM
Revealed inside

Twelve floors up with a 300-degree panorama of the bay, Coronado, Balboa Park, and the skyline. The classic San Diego post-dinner rooftop, dress code enforced, views unmatched.

+ 1 more
Revealed inside

It's the move when dinner went well and neither of you is ready to call it a night.

Planning a night like this yourself can take 4–6 hours. Here, it's already done, yours to download in seconds.

5 complete date nights, every one chosen and mapped, yours for $5.
Perfect for
AnniversariesFirst datesA night outSpecial occasions

Unlock all five, $5

A note from us

From us to you

We've done every one of these date nights ourselves.

Some are where we celebrate birthdays. Some are where we take friends visiting San Diego. Some have just become our favorite “we don't even need to think about it” go-tos.

These are the date nights we recommend to the people we care about most.

Now go enjoy it,

The Five On It
Stop planning. Start going.

Five date nights in San Diego, ready tonight.

Pick one, make the reservation, and go - the hard part is already done.

Unlock all five date nights

Instant access to your web guide, printable PDF, and map.

Or get it inside the San Diego, All Guides Bundle, $15 →