We were there 2 weeks ago (MM also) and used Spotify - You can get a free premium account for 30 days and download songs to your device which allows you to play them without wifi or data. On Board we connected our iPad to the stereo via a usb/lightning cable. Worked well. As others have indicated Pandora won't work. The digicell wifi works well (except Norman island). We vacuum sealed meat and packed it in a RTIC soft cooler (checked bag) - had to pay $10 duty on entry into Tortola. Our food stayed frozen solid so you may be able to bring as carryon without ice if you have a good cooler.