South Bay Area Date Ideas: Date Night San Jose, Palo Alto, Peninsula, San Mateo
First Date Ideas South Bay Area, Fun Date Spots San Jose, Date Night San Mateo, Date Ideas Palo Alto, Date Night Ideas San Jose, Outdoor Date Ideas San Jose, Date Ideas Sunnyvale, Mountain View
Updated: May 18, 2025
This is an assortment of date ideas in/around San Jose to San Mateo from fun date spots, upscale bars, outdoor date ideas and casual date ideas for first dates and more.
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Date Ideas San Jose, Romantic Restaurants, Santa Clara
For Bay Area date ideas in San Francisco, Sonoma/Napa, Marin, Oakland, Berkeley, Palo Alto and beyond, check out my other guides below:
This list will be updated over time, check back often (there will be a timestamp posted at the top).
Date Ideas South Bay Area, Date Night Peninsula
Be sure to check out my other guides as well!
Bay Area farmers market schedule (complete list by day, time)
If something is outdated or no longer active, let me know. I verified all the places below directly as of the date above through calls, emails and messaging establishments directly.
Unique Date Ideas Palo Alto, San Mateo, Sunnyvale, Silicon Valley Date Nights
Los Altos Stage Company
They produce several shows a year, and it’s a great, intimate venue with incredible set design and incredible performances.