Planning a wedding in Italy from halfway around the world hasn't been the easiest, but it's really not so bad either. Luckily Daniele is Italian, which has helped, but because of how popular destination weddings in Italy are for Americans, British, and Australians, planning for all us non-Italian speakers isn't THAT much more difficult than planning in our home countries.
With the language barrier out of the way, one of the most difficult parts of wedding planning for a destination wedding is not actually being able to physically see/taste everything. I know I am taking a leap of faith trusting reviews, photos, Google Earth, etc when it comes to making a decision, but that's why I've looked at my wedding options from every angle before pulling the trigger.
Keep in mind these tips are for the type of wedding Daniele and I are planning, we're opting for an intimate symbolic ceremony (meaning no legal paperwork to fill out) in a rented villa with a focus on a relaxing break for both our families and on good food. Still, the tips below are applicable to other types of weddings as well.