I've been fascinated by kiteboarding for a couple years, but have always been reluctant to buy a kite. It seems like every year, I take a land lesson from a new school in the bay area, and I get to the point where I'm taking water start lessons, and I always get days where there's almost no wind, I get down on the fact that I'd made it that far and still wasn't riding, and I don't go back or I get preoccupied with other things. Last year I got much better than previous years - I was actually up and riding during my last water start lesson.
I haven't been out yet this year as I'm training for a marathon that I'm running the first week of June, and I've had a number of back problems (herniated discs, pinched nerves) in the past 2 years (I blame surfing, cable boarding, and a weak core), and I don't want to risk not running the race. I plan to go chat with the folks I'd taken lessons from last year and see if we can jump straight to water start lessons again just after the marathon.
Shortly after that, I'm taking a month+ long vacation from work, and frankly while I have a quick stop in Seoul and Bangkok for a week to see some friends, I have 3-4 weeks after that with no set agenda. My general thought is it's now or never, make or break, to finally dedicate time to picking up the sport, or move on with my life. I realize the bay area is one of the best locations this time of year to kite, but I'd like to be able to sit on the beach without a shirt on, and get in the water with shorts on. I know that Oregon is an option as well, but that's not really a vacation for me (another issue). That said, I've been browsing around, and it seems like a couple relatively cheap options that match the rough criteria I'm looking for are Paros, Greece and Cabarete, Dominican Republic. Frankly, I could do both if I were to actually catch on.
Any recommendations on a) whether or not it's a bad idea to 'go all in' and commit to the trip, b) should I take a kite+board+harness (I'm sure that I'll want a seated harness due to my back complications) with me and just get lessons there, c) recommendations on Paros and/or Cabarete, is one better than the other, recommendations on where to stay, etc?