At the beginning of the Gulf Intracoastal Waterway, where the Caloosahatchee River enters San Carlos Bay and the journey northwards enters Pine Island Sound, there are enough places to anchor for a month of Sundays.

Leaving the river you can find shelter from winds from any direction except the southwest at Glover Bight in 6 feet over a sand and mud bottom. 

To the northwest of Punta Rassa there is good anchoring between Fisherman Key, Kitchen Key, and Big Island. Enter from the south a little past day marker G”11”. Depth is up to 11 feet over a shell bottom.

Dipping down into San Carlos Bay and Estero Island, you’ll find spots at Matanzas Entrance in a “No Wake” zone in about 8 feet. East of the bridge drop anchor in the deep water of Matanzas Pass, or go further down to day marker R”4” and find good holding in mud at 5 to 7 feet.

If you run straight out of the river to get into the GICW (Gulf Intracoastal Waterway) you can spend the night off pricy Sanibel Island in good-holding sandy mud. This spot is open to winds from the northeast through east, though.

At Buck Key by Captiva Island you’ll find good holding in 4 to 5 feet over sandy mud. There’s good protection from all directions except north winds. Then, at the north end of Pine Island Sound you will find a number of spots to drop the hook in and around Cayo Costa or at mile 28.5 of the GICW on Boca Grande.

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