If you are heading South of Sanibel Island it would be best to round her on the Gulf side and avoid the "miserable mile" on the ICW. Your last good pass to get out of the Pine Sound would be Redfish Pass in Captiva. There is a good anchorage off of Useppa Island (Private resort, no services) but you can dingui to Cabbage Key (good restaurant). We use anchorages when in transit to catch up on some sleep but for recreation in the area you cannot beat the marina at the South Seas Plantation in Captiva right of the Redfish Pass. Around $2.00 a foot buys you a resort with swimming pools, showers, store, restaurants, BBQ grills, trolleys and water sport amenities in the lap of luxury. A rental car agency on premises can open opportunities for land exploration and provisioning. Watch your draft in the area as the water is skinnnnnny.