San Jose in January

April through June gives you perfect weather without the summer crowds that hit other Bay Area destinations. Temperatures hover in the 70s, and you can actually find parking downtown without circling for 20 minutes. September through November works just as well. The heat breaks, and fall events like Cinequest Film Festival bring energy to the downtown core. Plus, hotel rates drop after summer travel season ends. Skip December through March unless you love gray skies and occasional rain. It's not terrible weather, but you're not getting the California sunshine you came for. Summer gets hot – we're talking 85-90 degrees regularly – though evenings cool down nicely.