I would avoid even the $10 a day plan and download a free wifi calling/messaging app like whatsapp or iphone's facetime/imessage. Put your phone, and all attached devices, like apple watch, tablets, etc., in airplane mode as soon as directed on your outbound flight and don't change that until you get back to your home country. I use a VPN and use whatever free wifi is available wherever I am- hotel, bars and restaurants, etc. Even if you need to check in frequently at home you can do so on a wifi only device (like an ipod). If you need to do a lot of work related stuff, I would contact your service provider directly to see what options you have. If you do use the $10 a day thing, just plan to do $10 worth of activity in the 24 hour period you are allowed- this is not a good option for a once a day text or call check in. You can also consider a digicel or flow phone with local and international text, talk, and data plans, see the websites or a local shop for details.