Alexa,
I would suggest you start by finding a social group where you can practice your skills , heading off into the RW and isolating yourself in a holiday maybe a step too far .
I picked a wet/ cold Monday morning when I ventured into Boots to have my skin colour checked but it was the best thing I ever did . OK I was in male mode and there were shoppers passing by but I was shown how to apply the products and walked out with confidence knowing the makeup was suited to me . Make overs can be expensive and often go OTT , just take a good look round at GGs and see how much or little most of them wear .