For the winter months, there were two "sun" locations that weren't too far away: Bermuda and Florida.
As the author described, new flying options and generally cheaper fares have upended the old vacation order. People are also more open-minded to going places that were never considered as vacation destinations in the past, such as Iceland (only 4 hours from Logan).
But a few strange geographical outlooks remain. For road/train vacations, for as long as I remember, the dominant perspective has been focused on New England, New York City, and maybe Washington DC as a stretch (7-8 hour drive). Montreal is less than 5 hours away but I never knew anyone from my generation that went there until we were in our 20s. Other parts of Quebec and the Southern Maritimes and Northern New York are still basically terra incognito to 90% of the population of Boston. It seems further away even though these locations are closer than Washington DC.