Coastal points along the way
Presuming you will be taking a coastal route I'd recommend some anchorages I've enjoyed. Just south of the Sanibel causeway there is "New Pass" on the north end of Big Hickory with 6' anchorage, but watch your depths heading in; the real estate to the north I bought with $675 in (TowBoatUS insured) towing charges. After a liesurely day's sail you could overnight at Marco Island, where you will see on your chart Coconut Key, another well protected anchorage inside that strip of sand reaching around just west (or choose local marinas upriver a bit). From there you can go offshore or upriver; the inshore route will save you time so as you emerge past Coon Key to Gullivan Bay you can tarry and find some of the best tarpon fishing in the area. Head south to Indian Key and head up the Barron River to Everglades City. This is the heart of the "10,000 Islands", and as you cross Chocoloskee Bay you will be enchanted at the site of the Outward Bound outpost directly before you. Head upriver past the Lodge (which U.S. Presidents have found suitable), and overnight at "Larry's World Famous Barron River Resort and Marina Chickee Bar". I wouldn't sail to the Keys without stopping here, but I must warn you to keep in mind your destination for an "overnight" here can turn into...ok, just show up on Thursday, for that's bingo night so locals and snow birds give it a real ecclectic flavor. The food is pretty good, too. Stone crabs are in season until the end of April, and then the whole town pretty much shuts down. Refuel before debarking, and leave on an outgoing tide for record speeds, for at times they have 6 knot current. Note: To really get the flavor go to Smallwoods store in Chocoloskee and buy the book "Killing Mr. Watson", and read it as you progress this trip. Your next overnight should be in what I call the Shark River basin, on the southwest side of Shark Island. If you arrive early enough head upriver through the mangroves to Oyster Bay, and if time permits further into Whitewater Bay. I have taken this route further to Flamingo into Florida Bay but don't consider it this trip (its the closest thing to impossible).Flamingo is your next hope for fuel, food, and shower if but a bit out of your way if you are hell bent on hitting the Keys, though accessible on your coastal route. I enjoyed this overnight for a cheap slip ($.55/foot last time I was there), and you may witness a salt water crocodile (no, not 'gator) indigenous to the area. Its worth it if by this time you have become enchanted by our Everglades. In Flamingo buy the book "Everglades: River of Grass". Read it when you get home, or better yet, buy it now and prepare for the adventure.If you bypass Flamingo and go directly to "Marathon" (Vaca Key) you will be going through a minefield of crab "pots". Good luck, and respect the fact what you are cursing are valuable to the owners, so go gently and stop as soon as you snag one. You will stop after you snag two, regardless (at least I did). Don't cut them free, but take the time to back off or dive and clear.Welcome to the Florida Keys at Vaca. After the causeway head east for fuel, food, and anchorage. Not my favorite. The next day you might want to stay at Cujo for secluded slight water anchorage, and then you will make Key West (your route in is well marked; good luck finding swing room). On the lucid side of your "Duval crawl" bring the family to the Wrecker's Museum. I'll leave you to the rest of the guides as to what is available there otherwise.Go to Garden Key and spend two nights. That's a whole 'nuther adventure and will take six days.Mark Major'86 H23 Lesismor