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Good anchorages from St. Pete to Ft. Myers???
There are several good anchorages along the way if you go down the intercoastal waterway. We like to stay a night at the Buchanneer, on Longboat Key (I believe) excellant food, nice dock. There is also a nice resturant on the northeast side of the Cortez Bridge. But it is noisey there at night from the sound of the cars crossing the bridge and lots of rocking from the early morning boat traffic.
If you can; buy, borrow or browse a copy of "Gunkholers Guide to the West Coast of Florida". This is THE authoritative guide to the area, with info on marinas, resturants with docks and good places for anchoring out too. I''m sorry that I can''t be more helpful myself, but I keep my copy on the boat. There are many, many places to hole up along the way, except for that strech just south of Sarasota. Even without a guide book, you won''t have any problem finding places to anchor out. But the book is well worth buying.
On that first night out, if the wind is strong from the north, you might want to anchor in the lee of the Sunshine Skyway on the east side. There is plenty of water there. Similarly, you can shelter just inside the channel in the Manatee River, just south of the big Indian mound on the north side of the river. Deep water very close to the shore, very sheltered from those sometimes nasty north winds that can blow this time of the year.
If the weather is nice, and you want to go down the coast, not in the ICW, Sarasota is going to be your best bet for the next anchorage. The channel there isn''t quite like my charts show it. Last time I went down it was running off way south of where it should have been. Watch the local traffic to spot the nun that marks the end of the channel and don''t try to cut any corners. There are lots of sandy shoals all around there till you get inside.
The area around Pine Island, Captiva Island, Gasparilla Island, etc is beautiful with many good spots for anchoring. But I don''t get to that area often and I can''t recall specific directions off the top of my head. Last year the pass at the north end of Captiva was not well marked (to my stranger''s eye) but easy to see in good weather. There is a much better marked pass north of there which most of the traffic uses.
Best wishes for a great trip.