Launch at county line marina after stocking in Fl. city. Cross key first night. (dog run beach but it’s tiny) from there, sunset cove, waterfront dining.(tarpon basin if you don’t want water front food) Next, islamorada, Lorelei restaurant district. Two days here because there’s lots of stuff to do on shore. From there, book it to marathon, and get any last minute stuff.(there a public park and ramp) Next day, stop at Ohio key, just past 7 mile bridge. Park in the cuts behind the small bridges. This is a very pretty place for kayaking. But don’t get hung up. Next, go down into big Spanish channel. (Leave Ohio key at dawn) If the tide is high, work your way across the shallows near the end of big Spanish channel to the content keys. It’s pretty shallow. If you don’t want to risk it, go out the end of big Spanish channel
and sail in the gulf instead. The access to Content Keys small harbor is vague. You’ll have to be able to read the water unless you have a GPS waypoint from someone. There is a very unpleasant rocky ledge near by. Do not do this in strong onshore conditions the first time. I usually choose the shallows option. Content keys and surrounding area is lovely. It’s very like the Bahamas.

Expect strong current in these cuts where you’ll be anchoring. From here, go to Tarpon Belly keys. This is popular with weekenders. There’s some other pretty areas to the southwest also. The Unpleasant Rocky Ledge is a recurring theme on the deep water gulf side of these keys so be careful. Don’t mess around there in bad light, or bad weather. Or check things out first in the dinghy. Further notes on this area: The scary “stars” (*) that can be seen on the chart on the shallow side hereabouts seemingly do not exist. I actually looked for them and couldn’t find them. There is probably also a bit more water here than shown. 6 inches probably. Some areas have considerable more.
So you’ve spent three days here and probably would like to not leave. Sorry. It’s time to return to Ohio key, Or go out in the gulf back towards Fl. Bay and then head for seven mile bridge depending on weather. Go under the bridge and and spend a night anchored by Molasses Keys. Both little keys are private property and landing is forbidden, but the surrounding water is very pretty. It’s a popular weekend place. Next, stop at boot key harbor if you need anything. It’s tempting to try to get Bahia Honda park into this trip. But that’s for another, lower keys adventure.
From boot key, stop at Long Key Bight and dinghy over to beachcomb the SE shore, OR skip that and stop at Indian key. This is a fascinating historical area. There are also some Atlantic reefs not too far away. From Indian key you have a choice: Return to the gulf side via snake creek draw bridge and return to Countyline marina, or continue to angelfish creek on the ocean side. Depending if your prefs. There are plenty of nice snorkeling reefs in hawk channel all the way to angelfish creek. Stops include Rock Harbor (last place to pick up any supplies) garden cove, old Rhodes key and nearby creeks. Then back to county line marina with a last stop at Alabama jacks and cross key.
This itinerary requires good anchors. 2, Minimum 25 pounds, chain etc. it assumes you want to anchor out as much as possible.
I carry a fifty pound fisherman anchor, a delta 12 (useless here) and an FX 35 fortress in the aft bunk locker. The fisherman has 80 feet of 1/4 inch chain and fifty feet of 5/8 nylon. All this is overkill but I just kept getting larger anchors till we didn’t drag much any more. (Keys are notorious for difficult anchoring) The ability to read the water depth is handy but not imperative until you get to the middle keys. Everything is pretty well marked but once in the Big Spanish channel/Content Keys district, you’ll be doing it by eye. Have good sunglasses. Spare prop too.
Ix

