There are a lot of variables including the amount of daylight, whether you are planning on sailing inside (on the ICW) or outside (the Atlantic or Gulf), the weather
, availability of anchorages
, number of crew, breakdowns, waiting for bridges etc. But in general, if you are motoring up the ICW, you can probably plan to make 50 to 80 miles a day assuming you can motor
at about 7 knots and you are stopping at night.
I can't tell you much about the trip to Miami and only a little about the trip from Miami to Clearwater, but for the leg from Clearwater to Mobile you will need at least
seven days and two or three weeks would be better. You could probably sail/motor directly from Clearwater to Mobile in about 3-4 days assuming you motored any time boatspeed dropped below 5 knots, but it sounds like you are more interested in doing day hops.
From Clearwater to Carabelle there is no ICW. You have two choices, either one of which takes you out on the Gulf. You can either go overnight from Clearwater to Dog Island/Carabelle (about 24 to 30 hours - anchorage at Dog Island, marina at Carabelle), or you can make a series of 50 to 80 mile hops along the coast. The first hop is from Clearwater to somewhere near Port Inglis (the best spot to anchor
here for a quick over night stop is probably the unfinished Cross Florida
Barge Canal), then to the Steinhatchee, then to Carabelle/Dog Island.
From Carabelle/Dog Island you can take the ICW to Port St. Joe (assuming your mast
height is less the 65'). Your mast
height will prohibit you from going all the way up the ICW to Pensacola
because of 50' bridges just east of Panama
City and beween Ft. Walton and Pensacola
. You will have to go outside at Port St. Joe and come back in at Pensacola.
At Port St. Joe you will have to go back out on the Gulf to Panama
City (a short 25 mile hop) for the night (good anchorages
and marinas), then outside to Destin ( 50 miles from PC).
You can go into Destin Harbor and anchor or get a slip, but cannot continue onto the Choctawhatchee because of the 50' bridge across the entrance. Be very careful going into the Destin pass. Try to get there with plenty of daylight, and preferably some sun so you can see the shoals. Call someone on the VHF
and ask for local knowledge. This pass shoals regularly and is often dredged so the deep water
could be anywhere. Sometimes is it ouside the markers!
From Destin it is another day (50 miles) on the Gulf to Pensacola where you can rejoin the ICW. From Pensacola, you can travel up the ICW (assuming your mast height is less than 65') to Mobile Bay taking either one really long day or two shorter days. Lots of great anchorages (and marinas of course) along here. Lulu's Homeport is about halfway and makes for an easy way to break it up.
In any event, it is a great trip and you will have a wonderful time, just watch the weather
and leave yourself as much time as possible. Trying to stick to a fixed schedule on a sailboat is one of the biggest reasons people get trouble. At a minimum, it will convert a great trip into a miserable trip. Worst case it can be a disaster. Take as much time as you can, go when the weather is right, and be prepared to leave the boat somewhere if the weather turns nasty. You can always come back and pick it up and continue on your trip.
Claireborne Young publishes cruising guides
to all the areas you are considering going and would probably help.
Also, try googling "cruising the great loop". Loopers cover this exact route
you are planning on doing (although usually in the other direction) and you should be able to get lots of information from them.
Have a great trip and enjoy your new boat!