Welcome and Congrats!!! I had a lot of the same questions and I know it can kind of be overwhelming at first. Don't stress about family and friends and how they will react. Some will be upset and others will be really excited. The best thing I can tell you is to just go with the flow and remember that it is about what you and your fiance want. As far as a date, I chose April 2013 because it is the cheapest time to travel that isn't during hurricane season. That being said, I don't have many children going so the out of school thing isn't really a problem I have to worry about. I am sending out my STD's this week so you are fine time-wise where that is concerned. The biggest thing you want to do is to make sure that you get word out to people so that they can start to make arrangements as early as they choose to. I chose Jamaica as I want it to be legal when we have our ceremony, and Jamaica has shorter residency requirements than Mexico does (2 BUSINESS days versus the 4 you would have to wait in Mexico). Just keep that in mind when you make your decision. We didn't want to worry about having to be down there a full week before we got married. When it came to bridesmaids, I simply met with each one individually and explained to them that I would love for them to be a bridesmaid, but since it was a destination wedding and I know it would be expensive, I understood if they just couldn't swing it. That way they can decide for themselves and know that I would be fine with whatever their decision was. The one thing I would suggest about a TA is to make sure they specialize in Destination Weddings. I cannot stress this enough. I went with the travel agency from this forum and Teresa has been fantastic about answering my questions. Just know that you will come up with many more throughout the process so don't worry about asking them everything in the first meeting. The first thing I would make sure you ask though is "what do I need to do right now?" They will assist you on what is a priority to decide and what can wait, and this information is EXTREMELY helpful. Either way, congrats to you and good luck! I hope this helps a little!