For me, our early holidays were spent on the East Coast, mainly Mablethorpe, as we had no transport, and could get there easily on the train (pre diesel), and the start of the journey was always exciting as the train used to go at the back of our house garden so my Grandma used to come out to wave. :)
I vividly remember in my early teens going to the Isle of Wight, and it was so exciting going on a ferry for the first time. Lots of lovely memories there.
My first flying holiday was to Sorrento. 3 nights, full board, with an excursion thrown in for £29! Beat that.
I will always remember too my first visit to Yugoslavia. To what is now Slovenia. Way up in the mountains, and a foot of snow overnight on my birthday! I have never lost my love for the place which is why I continue to go back.