I used to do similar trips with friends (pre-kids era)… each year a different country, so many places to choose from… just a few that I
recall off the top of my
head:
Croatia, Sardinia,
Corsica, Hyeres, Balearics,
Turkey, etc. for
Europe (avoid the densest months of Jul-Aug; we used to go in late April / beginning of May);
BVI,
Cuba,
Bahamas, Angra Dos Reis (BRA), etc. for the Americas…
I’m sure others have plenty of additional suggestions.
Fair winds!