i recently, just last month, sailed my boat from ft. lauderdale to tampa bay. the ideal conditions we hoped for did not materialize. the wind and tide clocked aroud with us as we rounded the state and, essentially, we had to fight a 20-25 kt headwind and 2-4kt current during each leg of the trip. fortunately, i had taken two weeks off work and used every bit of it to get my boat home. i am very thankful that when we really needed good weather, 50 miles offshore - sailing from key west to sanibel, we had it. so, if you go the long route here are some of the anchorages we used to duck and cover. each has good protection from all or most directions and good holding.
tampa bay - egmont key - probably the least comfortable and least protected of the group
venice - we rented a slip in venice at the crows nest, but i did make note of an anchorage just a little north of venice on the icw. i think it is in the area called "stump pass". if you are interested i could email you the numbers.
boca grande - there is an anchorage right across the channel from the cabbage key resort sign- umatilla key or idylewild key or something like that. good protection and good holding. only problem was the wake from passing big boats in the morning.
ft. myers beach - there is a mooring field in mantazas pass for $12/nite but if you go just beyond the mooring field there is an anchorage area with good holding and great protection from all sides.
*for groceries/laundry/liquor- if you dingy up the 4th(and last)channel from the bridge(heading west) there is a grocery store, liquor store, and laundry mat.
key west - rented a slip in kw
marathon - boot key harbor is well protected and well known.
islamorada - behind long key is jewfish hole. this one was recommended by a cruising buddy of mine. good protection from the east and good holding. it is labeled on the charts. i really liked this spot.
key largo - we anchored as far to the southeast in blackwater sound as we could. very close to the channel that leads to largo sound. there is a dingy dock behind the mexican restaurant that you can use. good protection and holding.
elliott key - this was my favorite anchorage of the whole trip. we anchored on the inside of elliott key on the way from miami to key largo. no development, lights, cars, cell phone service, etc..felt a million miles away from civilization.
miami - we anchored on the inside of south beach. good hold and protection but hard to find a place to dingy ashore to party on south beach.
ft. laudredale - lake sylvia - the locals tell you it is to shallow or that the marine patrol will run you off if yuo anchor there, but, we did not find this to be the case. it is a great anchorage and can be found on the charts. it is a great alternative to the $30/nt. mooring balls at the las olas bridge. thsi is probably why the locals don't like to talk about it.