hi, there, the wind here is very unpredictible, theres many spots, and if you want to go to all you need to have a car, holbox is an island like 2:3o hrs of cancun, isla blanca is like 20min north of cancun and yes you need a car to get there, or playa del carmen i do not recommend, tulum and xpu-ha are good for you, check
www.freestyleplaya.com, i do not know anything about a hostel in holbox, i know theres a campground close to the main beach, supervision depends on your skills, in holbox the beach is so big you do not need supervision, you should bring camping stuff and camp at xpu-ha and you can learn there, the spot is ok and theres a school if tou want help
