Are secondary alcohols more easily oxidised as compared to phenol? Which among the following compounds is oxidised most easily? 
  
  
  2-propanol ($\ce{CH3CHOHCH3}$)
  phenol ($\ce{PhOH}$)
  ethoxyethane ($\ce{Et-O-Et}$)
  1-methyl cyclohexanol
  


The answer given in my workbook is option 1. It's obvious to me that options 3 and 4 can't be the right answer (ether, hindrance). But I am confused between options 1 and 2.

I have arguments that can support either of the 2 options. There's less hindrance on phenol so formation of an intermediate ester like chromate ester would be easier their as compared to secondary alcohol. However, phenol is losing aromaticity as well, therefore activation energy of oxidation should be higher as compared to secondary alcohol.

Since $E_\mathrm{a}$ matters more, we would say that secondary alcohol is oxidised more easily, is it?
Hindrance has little to do with this. Loss of aromaticity is a big deal, so the oxidation of phenol to quinone takes a high energy reagent (Ceric Ammonium Nitrate is a good one). Oxidation of a secondary alcohol by contrast is fairly easy.