great trip you've got planned
You are gonna have a great trip! I'm kinda jealous

Anyway, the part from Marathon up to the Everglades will be one of the best parts of this trip. All the crusing guides are okay but they never really talk about the REAL Florida, the parts I'm talking about. I'm a born Cracker, these waters have been my home all my life. Nothing bad to say about Mr. Youngs guides but they don't tell the whole story. From Marathon you just head north. I'm sure you have the chart of Fla. bay so I won't go into details. It is about 30-35 nm from Marathon up to Little Shark River. Be patient with the winds before you leave the keys. If it is a north wind (cold front) than watch out, a SE wind (commen trade wind in the spring/summer) you'll have a smokin run north. As you get back up to mainland Fla. near Cape Sable in the afternoon you'll notice the sea breeze will fill in after 1pm most days if you are within 5-10 miles from shore giving you a nice ride up and into Shark River. If you want to see a really kewl place stop in at Flamingo. Your draft should allow you in there with no problems. I've been in there in my H33 with a 4'6" draft. The slip fees in here are cheep, it's great. You even have access to a pool and can kayak up the wilderness waterway. At the wall where you launch your kayak you'll find a resident salt water croc (he goes to both sides of this wall) along with bucket loads of the usual 6-10' gators. Be warned that the swamp angels, aka mosquitoes, can be unbelievable around here. I mean to the point that you will choke on them cause you can't take a breath without a mouth full of those suckers. Anyway, Flamingo is a still great stop. Little Shark River is around the corner just north of the three capes. If the wind is good you can anchor just off any of the capes that suites you and the winds. The beaches in here are totally untouched and natural (again, the swamp angels can be tough here too). If you make a single run to shark river it can easily be done in a single day from Marathon or Flamingo. The Little Shark River offers dozens of great anchorages that are safe in all winds including Hurricane Andrew (several boats rode out Andy up there with minimal damage). Feel free to head up the river to Oyster Bay, it is deep all the way up to the chickee huts and beyond. The currents in the rivers in here rip so be warned. Also, if you fish in here use serious line and leaders, the critters in here have bent my grouper digger rod to the breaking point and easily snapped 80lb leader wire more than once. Of course I've also cought nothing more than a bunch of bug bites. From Little Shark river it is about another 30 nm up to Everglades city where there are, again, at least six great anchorages or docks and reprovisioning. From Everglades city you can go around the Romano shoals or head straight up to the inside route to Marco Island via Goodland. Once you pass Coon Key and make it into the Marco River you'll have no problems in here either with your size boat. Once in the Marco River you can go all the way up to Naples on the inside route or jump out at Capri Pass (Marco Island) and head back up via the near coastal route. I recommend the inside passage just once, it is truly beautiful and undeveloped, for now......... Naples is trying it's best to ruin the rest of Florida like they've destroyed Collier county. From here I'm sure you know the way home. I've sailed these areas for many years on all types of boats from a 43' sport fish to a 23' Hunter, if you want any more detailed info feel free to ask. I've been there more than a couple times and will be going back a couple more. The Everglades and SW fla offer some of the best gunk holing in all the country, just have good mosquito netting.