Below is a very informative and interesting string of messages copied from the T&T (Trawlers and Trawlering) list about cruising from Marco Island in southwestern Florida, to either Marathon or Key West, then north to Miami or possibly even the Okeechobee Waterway. There’s tons of useful cruising tips here, over a wide ranging swath of waters.

I am interested in information related to leaving Marco Island and rounding the bottom of Florida, possible crossing over to the Hawk Channel at Seven Mile bridge. Anyone with experience, ideas, help? Thanks.
Craig McAllaster
“Cavalier” Island Packet SP Cruiser

We did just that about 2 years ago. It seems like yesterday but unfortunately that is a long time ago in cruising days. Our boat draws 4.5 feet and I would love to leave again tomorrow and do it in the same boat.
We made our way from Marco to Little Shark River, anchored there and left for 7 mile bridge. The water is skinny but you will get used to 9-10 feet and you will make it. Picking good weather is important. Many crab traps but just work your way through them. Go slow in places where dodging them is difficult and faster in open areas. Uneventful in crossing under 7 mile bridge. We had no tidal problems but I have heard of significant tidal flow so you probably should check the tidal flow times before leaving.
We did Hawk Channel to and from Key West. Plenty of water, of course, but we experienced extraordinarily rough water. When the wind direction is from off shore the long fetch can make things uncomfortable. Hawk Channel provides easy access to the Key West area but in my opinion, it is not worth it if the water is rough. Hawk channel is not close enough to land to say you saw any local color of the keys.
Now, if I had it to do again, I would take the bay side to key west. I have never been that way so do not have any direct experience but have heard many good things. Also have traveled by car to many places on the bay side and easily see why others rave about the “local color”.
Wayne Prichard

Craig,
You didn’t say what your draft is and that can be a factor in this part of the world. Also, you didn’t say how long you plan to be gone or when you want to leave.
Morning Star only draws 3-1/2 ft and we regularly leave Marco via Coon Key Pass. That makes a stop at Everglades City a short hop. Or you can continue on to Little Shark River for an overnight. The run from Little Shark to Marathon is not long and we have never found it to be particularly shallow. There are a few “banks” to avoid but they are well marked and if you are paying attention there won’t be a problem.
From Marathon, you can pass under the Seven-Mile Bridge at Moser Channel or you can go east up the ICW on the Florida Bay side or you can head west to Key West via Big Spanish Channel.
If you are contemplating Florida Bay, know that a strong northerly will blow a lot of water out of the Bay.
Finally, if your goal is to do the “South Florida Loop”, a trip we highly recommend, I would do the Okeechobee leg first and head south from Stuart. That way when you leave Miami and head down the Keys the prevailing wind will be at your back.
Regards,
Randy Pickelmann
MORNING STAR

We traveled directly from Naples to Key West on the Gulf. It was 122nm dock to dock and an easy run, although we did travel at a faster speed than usual. We left Naples at 7AM, navigated the crab pots and then never saw another pot nor another boat until we neared Key West! Took the Hawk Channel from Key West to Marathon.
ONE OLIVER II