Let me opine on the Tarpon Springs/Clearwater leg to the keys. I grew up in these waters and still
cruise them. While you are cruising south you may want to jaunt through Gulfport just south of Clearwater for a pleasant
anchor out and then on up Tampa Bay to the St. Petersburg area. There are
anchorages, moorings and marina's there. St Pete is on fire with activity and restaurants if that is your thing. South of the south Siesta Bridge in
Sarasota you will come to a spot where you pass two points--on on either side and the bay opens up. I anchor off the ICW to the west in 5 feet of
water and it is fine holding and protected. Heading back south toward Venice there are
anchorages off Marina Jack in
Sarasota where you can also dinghy ashore for some night life. The Venice area has gotten crowded with moored and docked
boats near the public launching
ramp. But, with your draft you should be able to find a place in Roberts Bay to anchor for a bit being unaffected by even the lowest cold front tide. Much to do in Venice and a short uber up to town or walk it in 20 minutes. If you go outside at Venice your next stop will be Boca Grande. If you go inside you will find some anchorages off the ICW north of the Englewood Bridge on the east side. you will see some other
boats that are permanently moored there. There is an anchorage just south of the Englewood bridge to the west. It can be crowded but offers easy dink access to the gulf beach. South from Englewood you will follow the ICW to the Charlotte Harbor/Boca Grande/Pine Island Sound area. Get a cruising guide and check this out for a plethora of anchorages with great
fishing, star viewing and the like. Don't miss Pelican Bay and Cabbage Key. You can go back out the channel at Boca Grande and
head south in the gulf or take the ICW down to Fort Meyers passing Sanibel and other nice stopping off spots. From there you have a decision to make. ICW over through Lake O. or down the coast to Naples/Marco or right on down to the Keys. One more caveat. If you are adventurous, I would encourage you to go into the Everglades at Little Shark River and anchor. I too am shoal draft and like to go all the way up to Whitewater Bay. This area is really
remote so be sure you are prepared for same. Hope that gives a little color. If you are in a hurry you can do long jumps. But, if you can wander there are many many nice areas on the
west coast of
Florida to gunk hole, dine and watch fab sunsets from. Have a hell of a trip!