Of course the wind direction will dictate where we tend to ride but here is a few ideas. There are plenty of spots to ride off a boat with miles of flats but the main spots are as follows. If the winds are NW we tend to hit the Cotton Key flats. A cool little sandbar with chop on one side and butter on the other. Most of the flat is about waist deep and a mix of sand and grass bottom. On a N wind we tend to hit the otherside sandbar. This is everyones favorite spot to ride as it is @ 3/4 mile long and butter flat. The bottom is the same as Cotton Key but also gets a bit mushy on the downwind side. Off land. For both directions is Founders Park. It's a town park and cost @ $5 to get in for non locals. The beach is small and a little sketchy for beginners as you are tucked into a cove. A few short tacks and you are in open water with a few small flats but mostly chop hop.
On NE wind there is Whale Harbor. $10 per day to launch. (sometimes) Huge open flats from ankle to waist deep. Also the starting point for a 5 to 10 mile downwinder. Epic! Most of us only do it on an E wind but you can do it on an E - SE wind. We also do most lessons and some off the best riding is at the Moorings sandbar. Huge sandbar but unless you are staying at Cheeca or The Mooring, a boat ride or downwinder are the only options. Good in NE - SW unless you are down winding. Then NE doesn't work. Last but not least is Anne's Beach. Free town park with flats near shore. Works on an E - SW. Limited parking and can get crowded with a very small beach.
There are tons of other spots throughout the keys but that would take me forever. Key west is @ 80 miles south. If there is no wind at anytime, there is always Keys Cable cable park. Plenty of other things to do.
oTHEerside Boardsports www.othersideboardsports.comwww.keyscable.com