Where to windsurf in October.

Question
My wife and I want to go someplace special to windsurf in mid-October for our 25th anniversary. I was thinking about Bonaire but that might not be the best time to be there. I am sort of intermediate level, re-entering the sport after a 30 year hiatus, and my wife is a beginner, having started last season, so we cannot handle challenging conditions. However, we sail now in our local body of water, the Chesapeake bay, which can get pretty choppy.
Would Hawaii be a possibility? Are there sheltered spots where one could rent equipment? This occasion warrants some loosening of purse strings, but cost is always a factor, of course.  Thanks!
-George

Answer
Hey George,

Congrats on 25 years. Hawaii, Maui specifically is probably the best place for wind in October. It should also be good in the Caribbean at that time of year. Check out www.velawindsurf.com for plenty of info for both areas. Check their wind charts for wind history. Their resorts have top notch equipment rigged and ready. Margarita is probably the best location for the level of sailors you describe yourselves to be. Also, plane fare from the east coast to the Caribbean will probably be less than to Hawaii. This is also one of the few places in Hawaii with gear on the beach. Most folks stay in a hotel or condo and have to rent gear in town and carry the gear on top of a rental car. Vela may seem a bit pricey but taking in all the cost factors of renting a car, gear, etc., they are actually a decent, no hassle deal.

Hope this helps.
Keep on sailing,
Windlover