Hi Snowcrow,
This is my first post ever so please bear with me.
My wife and I have sailed up and down the Caribbean and the US east coast over the previous three years.
The simplest approach we have found, after trying a number of different plans/phones, etc is to purchase local plans eg Trinidad when you get there. You might also have to purchase a cheap phone if yours doesn't work with their local SIM card. If you use a shop near the waterfront then they know what visiting yachties want. In the US we found that purchasing a local cheap phone at a supermarket and SIM card worked best for us. We also tried a plan but that failed when it came to topping up - we are also not US citizens so that made it more difficult. Coverage is spotty (big country). In Trinidad our mobile phone worked okey with their plan and SIM card. If you have to have a local address use the local boatyard where you are staying, or shopping, etc. Just top up as you need to via your mobile and/or local shops that sell you $20, $50 etc worth of calls and you just follow the instructions on the receipt.
Internet access in the Caribbean, for nothing, we found easier than the US where there are heaps of internet providers but that are generally secure. There were occasional exceptions around marinas and hotels. We often subscribed when at anchor for a few days or visited Starbucks etc to use their wifi. It was easier for us in the Caribbean. More freebies and also pubs, bars, marinas provide wifi - nice to answer emails and have a beer/coffee. There are also plans you can subscribe to short term just like in the US when at anchor for instance using a credit card. If you have internet access you will, more often than not, be able to use Skype. Skype is brilliant and you can even use it with a mobile (not that I have yet).
We were also after reliable weather reports. Enter Skymate, a satellite system. This costs about $1200 if I recall and you have to install hardware but it's not difficult to do at all and it works great through your computer or nav display. About $30 per month for our plan and you can turn it off for $6 per month when not needing it (like us - we sail for only six months each year). Almost worldwide coverage ie certainly covers all of US, Atlantic, Europe, etc. We can get NOAA weather reports anywhere, anytime, and also send and receive text emails anywhere easily.
I might add, we don't have HF radio (for now).
That's been our experience after countless chats, etc with fellow cruisers. I'm sure there are better and/or more costly solutions. Hope this helps and good luck.
