May move to malta

I love the winters. Cold is relative- I personally prefer winter over the horribly hot summers. Since you're active people I don't think you'll mind the winters (particularly after Massachusetts!) as long as you manage some indoor heating. I did an 11km hike a couple days ago with a group of friends (Italian, Polish, German) and it was beautiful and green, due to the rain we finally got- in summer I'm lucky if I feel like walking 11 steps. Also sitting outside cafes this time of year is nice because I don't find it too cold but the smokers do so they go indoors . Be prepared for that if you are non smokers- the anti smoking laws are not as good as in North America.
Yes, the driving is silly but it's totally manageable to live here without driving every day (bus/rent a car/Gozo is good for cycling). Some areas are more mini-England than others but not everywhere.

Thanks for your reply - we are considering a move to Malta in the near future for retiremnet. I am American my husband is an English citizen. We have read that we would be covered under the nation health. Are the summers really humid?

Sept is actually more humid than July and Aug but yeah, it is humid; it's def not Arizona-type heat. I was only here summer '15 (moved here 2 years ago, went back to Canada for 9 weeks this summer) and humidity really depended day to day. People said this past summer 'wasn't too bad' but none of those people were Canadian so I'm not buying it . I live a block from the sea so that helps for cooling down when it gets hot. You'll want to be within walking distance of the water because even though it's a small island it can take an absurdly long time to get around. It's not the most efficient place.

Compared to many countries the winters here are not cold, although quite chilly at the moment it is colder indoors than outside.  We do not normally get frosts and snow and last year was mild with very little rain.