If I understand correctly, you have a choice of departing from Biloxi or Galveston, so assume you are going to truck the boat that far. I would most definately do it from Biloxi. From Galveston to New Orleans you can go ICW or offshore. Neither is a good option. I have done it offshore and ICW and neither one would be considered fun.Offshore there are literally hundreds of oil
rigs. Some unlit, so a radar is almost a necessity. From Galveston to Biloxi is approx 500 miles offshore, and you will be far enough off to not have much of anyplace to head
in should the weather get bad. ICW is heavy barge traffic, not a lot of easy places to anchor and in some place diesel
can be a little hard to find. For example, Morgan
City, is easy to get 2,000 gallons of diesel
, but no one is very interested in 20 or 30 gallons for a sailboat. Once east of the Mississippi
the oil rigs pretty well fade away. From Biloxi you can go ICW as far east as Pensacola
, where you have to run outside as there are some 50' bridges east of there. But you can easily do this offshore in two day runs. From Pensacola to Pt. St. Joe is about a 20 to 24 hr. run. Pt. St. Joe marina is very nice, and bill themselves as the friendliest marina on the coast. Leaving Pt.St.Joe you can head
straight to Clearwater, or Tampa, or make an easy day run over to Appalachicola. This is a really quaint little town, with lots of eclectic shops. Worth a visit. From either Pt.St.Joe or Appalachicola to Clearwater or Tampa is a short offshore run, and you have to do it offshore. There is no ICW across the Fl. panhandle. You should be able to make Clearwater from Appalachicola in around 30 hours, and Pt. St. Joe to Tampa in approx. 48. And close in there is a lot of very shallow water
. At Tampa you can anchor up as soon as you get inside behind Edgemont Key, or a little farther in, in the Manatee river. Or of course you can do the Marina thing in Tampa or St.Pete. From there there are lots of neat anchorages
en route to Key West, or you could just do another two day run and be there. Nice anchorage at Marco Island, and in the Shark River.
You can go to cruises
, and find good anchorage info, marina info and fuel
prices for all of western Fla. and the Keys. Good luck and fair winds.