I did an all inclusive to Gran Canaria last Oct, it was paid for by my mother-in-law and it was a family holiday for the kids etc. They had a great time frolicking around by the pool etc. But **** me, more than a week of that **** would get dull. The first couple of days of free beer and food whenever you want is a novelty, but after that it's just encouragement to over indulge and make a ****ing pig of yourself.
My travels in the past have been way more off the beaten track. Plane ticket to Caracas and then try and find a hotel in the cheapest part of town, before speaking to some locals who'll take you into the Jungle to find some psychedelics. Since I've had kids, I don't take the same risks, but I've taken the little one up into the back country in Yosemite and out into Bear and Wolf country in Canada earlier this year.
The idea of sitting around a pool reading a book bores me to tears.