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For the big ticket items that I really wanted (venue, food, photographer) I actually booked those 2 years out (18 months-2 years). I felt like that was really early but it was so nice to get those things off my mind and know that they were set in stone! Then after that I hired my coordinator and she slowly started filling in the rest. By about 1 year out I had everything booked (hair, makeup, etc). Then it was just a waiting game for the last minute details. Overall this worked out great because I had plenty of time between when I placed deposits and when to pay in full (most people want the remainder about 30 days out).
Also, to rest your worries, I never did a planning trip or visited the venue or met anyone in person. I HEAVILY relied on this board, many reviews, and Yelp. I was worried at first, but once I got to the island and my big day came, everything went perfectly. Some small issues here and there may have arisen, but I was the only one who ever noticed and everyone had a great time. Planning from home can totally be done, but I would highly suggest at least a day of coordinator so you can relax and enjoy the day.
My engagement was 2 years, but that was mostly so we could save enough money to pay for it all, as well as that was the timing that worked out for me school-timeline-wise. Other than that, a lot of girls plan for a year, but I have heard of girls doing it a few months out as well. Just depends, because if you have your heart set on something you need to make sure it is available. Things book up fast in Maui, especially in the summer months.