For a guy in MA who hasn't traveled too much over 30 years and plans a 1 week Dec or Feb holiday, pick a spot in a manageable area, consider limiting the tendency to try to cover too much space, and increase the chances of enjoying yourself. During winter, I suspect you may want to get away from crap weather.
No snow, but weather might be something to consider with Ireland. Otherwise, that's a quick, easy flight from Logan to Shannon or Dublin (well, easy and quickfor someone familiar with much longer flights). Both Israel, which you mention, and Costa Rico, are good options for weather breakaways. Costa Rico has the advantage of diverse territory, topography, etc (Pacific, jungle, hill country), minimal time change / limited jet lag, and Las Ticas.
Happy to respond to questions via PM. During your summer breaks, your teaching background could easily pay for more travel - some teaching, lots of potential international experiences ...