I've a feeling that you already went... but thread resurrection seems a good idea, since I'm doing a 7 day trip in late March.
Chartering a 44 out of ST Pete, will spend the first day mucking about Tampa Bay,
learning systems with a
captain (we've chartered before, but this is bigger). Stay that night back at their marina, will go
provisioning after we return the
skipper.
Kids can swim while we shop, then we store provisions,
shower and dinner.
Day 1: Sail to Manatee River,
anchor upstream (Hooker Island) and visit a brother in law north of the bridges. Then return to the
boat, motor/sail to Jewfish anchorage just past Longboat Pass
Day 2: Long day sail Longboat to
Charlotte Harbor via Boca Grande, anchor behind the island. Obviously, this is only potentially possible... Early start is a must. A stop into Venice might be required, and either anchor to the immediate right, or secure a berth.
Day 3: Explore Boca Grande lighthouse, then sail
Charlotte Harbor to Punta Gorda. Marina at Fisherman's Village
Day 4: Day excursion Peace River via airboat Scheduled mid morning so a bit of "still arriving" time is available
Day 5: Sail Punta Gorda to points north, possibly as far as Venice
Day 6: Return to Bradenton/Tampa Bay area
Day 7: Return to St Pete Marina, fly out
Obviously, this is contingent on a cooperative
weather system. If the
weather is dicey, then we either cancel the Peace River jaunt, or rent a car and do it from a safe port further north. We have the Brother in Law in Bradenton who can help with those sort of logistics, or there is Uber
If weather is from the south early in the week, and not expected from there later, we will do Tampa Bay sailing, Gulfport/Clearwater/Anclote Keys, but will be limited by shallower water depths. I guess beach days or find a marina with a pool for the kids.
Ideal weather is steady winds from the west, but prevalent winds are usually from the east. That means lower water, but also means many
anchorages will be well protected. Once
offshore, east winds are great for sailing to and from Charlotte H, so I'm hopeful.