Having lost count of how many ICW trips I've made (north of 20), I have a bit of experience. Those who relax and take it during the right season, and don't push on when the weather is bad or out of season have a great time. I read so often of someone complaining about being too cold (you're either too early or too late), or hating all the bugs (you're probably out of season). Yes, there can be bugs, particularly after sunset, but some of the worst mosquitoes I've ever encountered have been in far north places in the summer (In Labrador you need a face mask or a bandana in order to breathe). And, the gnats can drive you buggy in the south too. However, most boaters heading south in the fall or north in the spring need to button up the boat at night to stay warm, so no bugs down below. The trick is to travel as the seasons are changing so that as you move along the season moves along with you and it is mostly pleasantly warm during the day, but a bit cool in the evening. It is also a good idea anywhere, even Maine in the summer, to have good screens for those unusually warm evenings. Just in general, those who have the best trips on the ICW take their time, go in the proper seasons, and don't try to stick to arbitrary schedules. In other words, they go when the weather is good, take a few days off every week, enjoy the places along the way, and don't kill themselves trying to make miles or some destination by a certain point. I also often mix in offshore jaunts when the wind is favorable, which can relieve some of the motoring blahs. Headed north you can often take long offshore legs since the good weather, prevailing wind is from the southwest/southeast. Going south is a bit more problematic, but it is possible to have some great sailing when the wind is from the north but offshore so the seas are low. Go inside and outside to break up the monotony of the trip, if you're getting bored.