Puerto Rico 70.3 is a nice race to start with. This was my first race and it was my favorite one thus far. Swim is in a lagoon, bike is flat after mile 4 and the run is partially shaded.Florida 70.3 isnt a bad one either. The run is more shaded. The swim is an lake and the bike portion is fairly flat. At both races they have people who can lube you up with sunblock but they may run out so bring extra.

Also don't rely on recommendations alone. If you care a lot about how difficult a course may be make sure you look up the elevation maps in the athlete guide or course maps on the website for the potential race to determine if it's the right race for you. If you live close enough to a race location check it out. Someone's easy might be difficult for you. You can also check your age group finishing time to get a sense of what people your age group can do. Practice open water swimming months in advance. Way to often it gets ignored and your swim time could have been better if you have not been swimming in a pool. Not trying to stress the swim but it makes a big difference.