Naples to Marathon (skipping all the upper keys) then to Key West then to Dry Tortugas in 3.5 days may be too ambitious, my friend!
That route should include some weather days. There is no protected ICW at Naples, or from Marco Island to Marathon. You’d be miles out into the unprotected shallow Gulf of Mexico with no cell service (there is a single AT&T pole at Flamingo per James on Molly Brown). VHF range is under 10-20 miles on a lucky day. Same for the 75 miles and 50 million pot floats between Key West and Ft Jeff. Check the battery expiration date on your EPIRB.
This week’s Tortugas MARINE forecast is here, note that true 3 foot seas mean every 100th wave will be 6 feet, ‘5 foot seas’ means every few minutes crashing into a 10 footer, etc.
Good luck with that. You’re going to need it.
https://forecast.weather.gov/shmrn.php? ... syn=gmz005
Take the seaplane instead...you’ll see more at 500 feet and have the island to yourself before the ferry arrives. Reserve far in advance.
https://keywestseaplanecharters.com/rates/
If you have only 7 days including weather days, consider launching and rig storage at Founder’s Park, Islamorada, and just exploring the Keys.
https://www.islamorada.fl.us/department ... /index.php
Another option is launching and rig storage at Garrison Bight City Marina, Key West, and exploring from there.
https://www.citymarinakeywest.com/
Cudjoe Gardens marina has a good ramp, but call re offsite rig storage and if they’d let you dock the boat there while you go arrange for that. In the Keys, rig storage varies with the varying ownership of typical mom and pop type businesses. If the lot behind a seafood shack was available last season, it may have changed hands by this season.
http://cudjoemarina.com/
Marathon has a good ramp at 33rd St beside the Yacht Club and a trailer sales place that stores rigs up the road, but there is no day dock to tie up to at the ramp, and only 8 parking spots that fill early. We use it when renting a Marathon canal house with dock.
Herbert Hoover Marina on Biscayne Bay has six good ramps and rig parking by cell phone app at kiosks, but we have never gotten a consistent answer on how long you can park your rig there.
https://www.miamidade.gov/parks/herbert ... marina.asp
Calusa Island Marina has an adequate ramp and on-site rig storage WHILE YOU ARE IN A TRANSIENT SLIP THERE. You could call re a 7-day exception. No waterfront business can afford to store rigs on site on the cheap.
https://shmarinas.com/locations/safe-ha ... sa-island/
In our rather extensive Florida travels, we have not found a suitable ramp/free day dock/rig storage option near Naples except for Burnt Store Marina ramp to the north (off site rig storage, call dockmaster for current into)
https://shmarinas.com/locations/safe-ha ... rnt-store/
And Port of the Islands marina to the south, just north of the Everglades:
https://portoftheislandsmarina.com/
If you find an alternative, please post about it.
We are really asking for a LOT:
Not just a ramp, but one that can float a CD 26 or TC255 (53 inches deep before the aft starts to float)...
That ramp also has a large free ‘day use’ extension that is safe enough to leave the boat while we spend hours arranging for off site rig storage, (the good ramp at Laishley Marina, Punta Gorda does have a long, free day use dock...Thanks James/Molly Brown for that find)...
or a co-operative Dockmaster who allows us to dock in an unused slip for free for a few hours.
That’s a lot to ask for!
PS: Note you must have an Everglades Boating Certificate to enter the Everglades:
https://www.nps.gov/ever/planyourvisit/ ... rogram.htm
Best of luck on your most excellent adventure!
Safe travels, and hope this is helpful.
John