Colorado to Marathon ... 2 weeks with our boat.

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How many wheels on each side of the trailer? I'd get that many per side, ie, if two wheels on a side, carry two spares- minimum. Reason is, whatever flattens the first one will likely flatten the one behind it; now you're stuck until you get one tire into a town to be fixed if you only have one spare. That may not be easy on a evening or weekend.

I would also think about getting another wheel for the truck. Same reason, and if your truck is disabled, you can't just get a tow truck with a boat attached.

Extra lubricants and coolant for the truck.
A full shop/ trained expert checkout wouldn't hurt.
Do you have a trailer lock?

I would invest in a good boating safety course focused on the ocean, I'm sure Wookie could recommend one, and there could be a Coast Guard Auxiliary near you as well. The local Coast Guard station (Islamorada, IIRC) may be able to help as well. They may be willing to help by inspecting your boat too. Ask Wookie, he probably knows the most of anyone on this board about that area.
I second all this. Towing is a big deal that far. I towed my 21 footer from Tampa to Key West and blew 3 tires. The boat spent the night on alligator alley while I searched all over Weston for spares.
 
A marine handheld at a minimum with a remote antenna. And understand how it works. Please don’t become a story the locals tell. But it is a great adventure And I envy you.
 
Thank you for your input tekkydiver but we're doing it - it'll be an adventure!

Sounds like two spares is the way to go.

Handheld it is! We're not risky people, but love an adventure - thanks for all the advice!!!
 
A marine radio is a must have. You'd be crazy to go out without one. I don't own a boat but used to dive off friends boats when I lived in FL and none would ever go into open ocean without one.

If you live in FL long enough you'll hear too many stories of people taking small boats like yours out, getting hit by a storm and running into problems with no way to contact anyone for help

Five or six years ago, a guy took a small (24 foot maybe) center console with a single outboard out one of the Palm Beach inlets. He had engine trouble and no radio. Needless to say he was extremely lucky when a worker stepped outside to take smoke on a passing freighter and just happened to spot him drifting several days later two states north of florida. Then there's the story of the two young, but experienced, boys who took a fishing boat out in rough seas in Jupiter and were never seen again.

Get the radio. Get a good one. Don't be cheap
 
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I always thought of the nautilus lifeline as a hand held marine radio. Perhaps I was wrong - or maybe people are not familiar with it?

But of course there is a bit of a learning curve going on, so now I am looking into marine radios ... also looking at Sat phones instead as that would be useful for our back country hikes too.
 
This sounds like a bad that will likely end with great stories.
Good luck.
Post pictures daily

I would fly and rent the boat. At least then someone in the Keys will try to find you if you get lost or stuck.
 
Bring the boat, have a ball, and the best chance of that happening is if you stay inshore and close in Gulfside, use the boat for boating (not diving) and, by and large, stay off the ocean. If you're on a budget make sure you've got towing insurance for on the road and on the water. I'm sitting on my deck in Big Pine Key as I write this, looking at the dock in my back yard (sans boat), had a great week of diving, and 20 years coming here have never been easier or better. Best of luck...sincerely.
 
I can't help with the boating information, but we raise cattle and pull lots of trailers. I own 6. First, repack the bearings with quality synthetic grease. Second, 2 good spares for a tandem (double) axle trailer for a trip that far. Third, go to Sears or harbor freight and by a laser thermometer. When you stop, shoot the temperature of the hubs. Before one fails, it will be significantly hotter than the rest. The Palm of your hand works....but the pistol laser thermometer is better. Fourth, if you have friends or family along the way, make sure you have their numbers in case something goes wrong. If you have problems with 40 miles of OKC (if you come through OKC), shoot me a message. Fifth, carry tire plugs (a kit is available at Walmart cheap) and even one of the cheap 12 volt compressors is better than nothing, a few cans of fix a flat is not a bad idea either. I've used screws to patch a tire until I could get somewhere safer. I just don't like to be on the side of the interstate changing a tire with 80,000 pound semis a few feet away. Sixth, have fun!! Be warned, a big boat with Colorado plates, will probably be stopped for a sniff or two by local police.

Jay
 
I'm sitting here with my husband reading this entire thread. We are laughing and understand we might sound crazy to some! We are taking in and listening to all the advice. I am going to add a bunch of stuff to our must have list. This is why I posted - I wanted to hear what experienced people had to say.

Jay - Thank you for your post (and offer as a savor!) lots of great info that we will heed/buy. As a Coloradoan I am well aware of my odds of being pulled over; we will make sure to clean out the glove box and center console for any leftovers our guests shove in there on the way to the airport lol!

If it helps put anyone's mind to ease - my husband was a Navy nuclear engineer, so he is mechanical and no dummy - he is my saving grace when I come up with these crazy ideas! Thank you everyone for your candor! I plan to post once we take off - and any updates on our adventure!
 
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http://cavediveflorida.com/Rum_House.htm

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