Winter Date Night Ideas in La Jolla, CA

Best winter date nights in La Jolla, CA include George's at the Cove (Rooftop entrees $25-38, fine dining $40-60), Prospect Street / La Jolla Village (Free to walk; First Thursday galleries free), The Comedy Store La Jolla ($20-35 cover, two-drink minimum), The Cave Store / Sunny Jim Sea Cave ($10 adults, $6 kids 3-17), and Torrey Pines Gliderport (Free to watch; tandem flights $175-225). Add ice skating or a holiday lights walk for the full seasonal experience.

7 places4 freeOct 2026
The Cave Store / Sunny Jim Sea Cave

145 steps down to the only land-accessible sea cave in California — $10 and unforgettable

1325 Coast Blvd, La Jolla, CA 92037 · Daily 10am-5pm

$10 adults, $6 kids 3-17
Museum of Contemporary Art San Diego

Contemporary art with an ocean-view terrace — free if you're 25 or under

700 Prospect St, La Jolla, CA 92037 · Thu-Tue 10am-5pm, closed Wed

$25 adults, free 25 and under
The Comedy Store La Jolla

Since 1976 — same Comedy Store lineage as Sunset Blvd, intimate room, six nights a week

916 Pearl St, La Jolla, CA 92037 · Shows Wed-Mon, typically 8pm and 10pm

$20-35 cover, two-drink minimum
Shell Beach Tide Pools

Free tide pools at low tide — sea stars, anemones, and crabs right at your feet

Coast Blvd S at Cuvier St, La Jolla, CA 92037 · Open 24/7; best at low tide

Free
George's at the Cove

Rooftop ocean terrace with no reservations needed — same views, lower price point

1250 Prospect St, La Jolla, CA 92037 · Daily 11am-9pm (rooftop); fine dining Thu-Mon 5-9pm

Rooftop entrees $25-38, fine dining $40-60
Prospect Street / La Jolla Village

Walkable village with galleries, boutiques, and ocean views — First Thursday Art Walk free

Prospect St, La Jolla, CA 92037 · Most shops 10am-6pm; restaurants to 10pm

Free to walk; First Thursday galleries free
Torrey Pines Gliderport

Watch paragliders launch off ocean cliffs for free — or tandem fly for $175

2800 Torrey Pines Scenic Dr, La Jolla, CA 92037 · Daily, weather permitting; flights typically 10am-5pm

Free to watch; tandem flights $175-225