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I grew up in the Boston area around the same time. Another factor that limited interest in flying to sunny beach places was we already had options close to home during the warmer months, such as Cape Cod, Cape Ann, Hull, Rhode Island, Southern Maine, and so on. Lots of people including families of modest means had cabins in these areas.

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.

It really is surprising how much air travel has changed during my lifetime. I remember feeling like kind of a loser in (public) high school back in the 90s when a select few kids would return from some exotic location for the winter break. But the consolation was that at least, like me, none of my friends went anywhere. There was one kid in my friend group who had flown once before. But if I recall correctly, it was to visit a divorced parent or something, so even though flying struck all of us as a crazy and aspirational way to travel, we all still felt bad for him.

By the time I was in my 20s (in the early 2000s), the situation was totally different. The most ridiculous: sometime in 2009, JetBlue had a deal, announced on radio, that you could purchase unlimited flights for 3 months for only $500. As my fiancee had moved to the western US for her medical school residency program, this was a godsend. I visited her every weekend... I don't remember if I took a full 12 trips, but it was more than 10. I would leave Boston immediately after work on Friday and then take a redeye and arrive back in Boston at 7am on a Monday. I haven't seen a deal like that in a long time, and flying has increasingly gotten worse since that experience, but it still is relatively affordable compared to my high school years.

> The cruise ships still make their runs, usually in the spring and fall, and they remain popular. But if you’re going by air, today your options are JetBlue or a tiny upstart called BermudAir, both using small jets.

I work with that tiny startup! Bermuda Air has been a fantastic partner for us developing automated routing/alerting for pilots, dispatchers, and ops.

We even got to do some work during the big hurricane season last year. Pretty special to see your code operating in that real of a real-world application.

This must be Bermuda Week. Just yesterday I saw an interesting video about Bermuda from Geography by Geoff:

https://www.youtube.com/watch?v=0NVb5M7m9xg

Great photo up top, of author's family members entering the "America[n]" airliner.

Not much meat to this article, but I do wonder how much lower prices were then in Bermuda. Almost everything needs to be imported and shipped over. Today, it is incredibly expensive. You can easily pay $30 for an incredibly mediocre breakfast (though cheaper options can be found, if you look).