I think Rick (BEERMAN) covered most everything. I'll add what I can.

When we first we're looking at the trip, we really didn't have too many concerns that wouldn't have been a concern anywhere else we might go - they are just a little different (hotel rooms have risks for example..). Weather forecasts are pretty decent these days and we wouldn't have put ourselves in a position of being in a place under bad weather. If there was going to be a big storm, we would have left or possibly not even gone down. Since trips are booked ahead of time, those are decisions you need to be willing to make - might be good to have insurance. Fortunately, we had great weather the whole time.

The other concern we had, even though he had no signs of allergies was if he had an allergic reaction. So we got an Epi-pen just to be safe. Never had an issue here either.

Safety around water and while on the boat we're the only other two concerns. We simply made sure he always had his life vest on and was always supervised.

Mosquito's we're never a big concern. I'm sure many wouldn't think twice of spending a week on St. John or St. Thomas with a little one and I think the risk of mosquito's is greater on land. We simply covered up when needed and put bug spray on whenever we went ashore. Mosquito's are a problem at home too and we just take the same precautions.

He's been on 4 trips so far, all prior to turning 2 (he just turned 3 a couple weeks ago) and we had a great time on all of them and he did too. He wants to go again soon (as do we)!

The one thing that has become easier is each trip we managed to bring a little less stuff. First trip, we had a LOT. Diapers, baby food, you name it. 2, 3rd and 4th trip he was 1 and was eating regular food, so that made things a lot easier. We also stopped bringing the pack n play as 1) it was one more large thing to bring and 2) he was too big for it. Sleeping in a cabin worked great and we just brought our camera baby monitor so we could keep an eye on him. Having shore power or Genset are key to have stuff like that running.

Happy to answer any specific concerns or anything like that. We've always pretty much taken him everywhere with us. And we are glad we did these trips with him as we all had such a good time (did I already say that?). I think the other thing that made it easy was the great crew we had each time as well! Everyone spent some time with him here and there.

Here's some pics from that first trip - Album will expire in 60 days - just an FYI for anyone reading this later on.. https://1drv.ms/f/s!ArF5dENynbvii6czLihYjHi2oIhS6g

Our trips we're on a few different boats. One on a Moorings 4800, One on their 4000 (that was our favorite due to the forward galley and essentially large play area he had inside - we just had to block off the stairway to each hull. Then we were on our boat for 2 trips which was great too and where he had his own cabin (or shared cabin with us). I'd suggest a cat, but a monohull would be fine too - larger with A/C would probably be preferred, but something with shore power would work too. It is easy to spend every night on the dock if you want to.

Since we've done this many times, I'm happy to answer any specific questions or concerns. Feel free to comment here or send me a private message.

Matt