Christmas Cruise-West Coast FL, Dry Tortugas and a cheap place to leave the boat?

[DreaminFred]

Hi all-

Thanks for all your feedback to my distance cruise planning questions in the past! For those of you who don't remember- I teach at a college in AZ and have a Pearson 365 on the Withlacoochee River north of Tampa about 80 miles. Did a satisfactory shakedown cruise in May (bought the boat in March) and am now planning about a month cruise over Christmas break. Thinking I will make a long day sail to Tampa, then slow down hopping down the Nature Coast. Then want to go out to the Dry Tortugas for a couple days of anchoring/snorkeling. Then over to the Keys? But after the Tortugas, the real end goal is to have the boat in a good yard for the rest of the winter/spring for further upgrades with an eye to sailing the Bahamas in Summer, 2018.

I'm looking for local knowledge regarding special events (holiday related?) on the west coast, favorite anchorages south of Tampa and your ideas about a (relatively) inexpensive place to leave the boat. I've heard about a place on the canal near Lake Okeechobee, how long would I need to plan to get there from say, Miami?

Thanks.

Fred