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TAKE ACTION AND MAKE IT HAPPEN
The best way to make a trip happen is just to book a ticket and let the adrenaline make everything else fall into place.
However, there are some key things to check out first. ALWAYS check out the health and safety advice for the region you're travelling to and make sure you're up to date with any recommended vaccinations and healthcare procedures. After that, it's up to you whether or not you book accommodation now or figure it out when you get there - or whether you'd prefer to let someone else take care of all the logistics for you through an individually designed tour.
For my general recommendations on equipment, tour operators and more, visit the Travel Resources page. For tips specific to Italy, read on below.
As ever, with any advice you find on the web, this is meant for help and guidance only. Always check with your own doctor, embassy, lawyer and spouse before making any irreversible plans...