Best summer song No. 2: Summer Wind - Frank Sinatra
"Summer Wind" has a slightly bittersweet ending, but that's only because summer ends eventually and turns into winter. But the point of the song is the happiness and relaxed celebration that is, in fact, summer and the memories it can yield. I could have gone with many different versions of this song as it was originally a German song called, "Der Sommerwind" (of course, duh!). But lyricist Johnny Mercer re-wrote the song into English and lots of artists eventually wanted to sing it.
Frank Sinatra's version wasn't the first English language edition of the song (Wayne Newton, Bobby Vinton, and Perry Cuomo tried the song before Sinatra), but as Sinatra is the GOAT of his genre - and his version helps prove why - then the Sinatra version of "Summer Wind" is the one you should be playing among family, and friends, and cats.
No one ever sings a tune the way Sinatra does, just slightly behind the beat. That helps the listener feel enveloped in what he is telling and helps the song feel like home. Sinatra's version of "Summer Wind" is just so laid back that invites those who have been chilling near the fire pit to just be quiet and enjoy each new moment they are living in.
Sure, Sinatra is such an incredible artist that you can sense the bittersweetness of summer ending. But there also seems like he takes some umbrage with the gall of autumn and winter taking over from summer and reverts backs to the memory of a wonderful summer evening.