Trap:
I wish I could...my computer technical expertise is in short supply. I tell myself I need to devote time to get a tighter grip on "copying" "pasting" and the assorted other aspects of Modern Day Living. It never seems to get done.
Please refer to Planned Outage's map that you see on this thread. Note that he maintains a Southerly track and that track takes him further offshore once South of Cape Romano. The only difference in his and my track is the heading. I bend SSE toward Marathon while he heads directly to Ramrod Key.
It is indeed a neat trip, loaded with variation. You get the "Sun Coast Florida" Vibe in spades as you motor past the white sand beaches in the foreground, backed by the kick-butt Hi-Rise Condos that line the coast all the way to Marco. From there around Cape Romano, it goes to complete Wilderness with no facilities except for Everglades City.
During the times I run close in to the Everglades to escape the chop on windy days,, all I see are endless mangroves along the shore, and the only people I encounter are indifferent local fishermen in flats boats who barely look up as I motor past. It is within this stretch of No Man's Land that I always come to grips with the insane price I paid for my dependable Yamaha OB's. In the event of engine failure, your companions are sharks, saltwater crocs (infrequent), and alligators (everywhere) in the brackish backwaters. Your VHF is your best friend....
There are tributaries off the Gulf to escape storms or to explore and/or fish. Shark River, North of Cape Sable is the most notable of these and is well-marked. I have friends who anchor inside the river mouth; sometimes they have trouble getting a "Set" on their ground tackle, due to the hard clay in the seabed, but they have all passed comfortable nights there. Bug spray is as essential as life jackets during the warmer months and I don't think it unlikely that on a still night, Captain & Crew could get carried away much like the Flying Monkeys carried Dorothy & Toto to the Witch's Castle.
Planned Outage:
Thanks for the kind words and for putting your track up. You are correct describing Fla Bay; It can be a marvelous cruise or a Trip That Never Ends, depending on wind.
Your Canyon 33 would rock on a run like this; I'll bet it's a great ride. I have to duck & dodge waves & wind over 10kts.
I also concur that a 271 would be a good choice.
RAYK:
Hookup1's shore side accommodations are good picks;
I have stayed at both places and highly recommend. Faro Blanco is an easy, straight-in approach and has a Hyatt Place on site. Hawks Cay has a marked channel & perimeter canal that you transit to get there. It's just West of the Long Key Bridge on Duck Key. They just rebuilt after Hurricane Irma in 2017..I have not stayed there since, but I'll bet it's still top-tier. If, as you mention, your Bogey is Key West, Galleon's Marina is the go-to joint there. Equipped with floating docks, good grouper sandwiches, and all the weirdo's Key West is famous for, it is indeed a memorable stay.