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Dec 23, 2017
I’m a northerner but on occasion have chartered boats in Florida. I’m contemplating a charter out of Fort Meyers, heading east on the Caloosahatchee River connecting with intracoastal waterway and heading south and returning to Fort Meyers via the Everglades. How long would this take? I’m thinking it might be a nice week long charter.
I think you can make the trip but wouldn’t leave much time to enjoy the nice and differing areas you will travel through.

I’ve done the trip in segments but with a fast boat. I’m guessing you’re talking a slow Trawler. Ten days might be more fun.

Someone who has actually done it in a trawler will be along soon to tell you better than I can.
If I was going to do it, I would consider going in the opposite direction. Depending on the time of year, weather can be a big factor on the part from the Everglades to Fort Myers. You will be exposed to the Gulf as opposed to the rest of the trip which can all be inland waters. If the weather doesn't cooperate, there is other inland cruising you can do instead. Would suck to be trapped in the Everglades waiting for a weather window and miss the flight home, etc.

Well the first day you would need to load provisions and get your check out with a captain. Half day. Crossing Lake O to Stuart, two and a half days. Stuart to Miami at least two days. Miami to Little Shark River at least two days. LSR to FM Beach at least one day. FMB to FM, another half day. All this assumes good weather.
I would say two weeks minimum if you want to “cruise” vs “deliver”.
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Some charters restrict the areas where you can cruise due to insurance issues. If I am not mistaken, most of the FL west coast charters restrict you to the west coast. Check that out before making plans. They may provide a wider cruising area for more bucks.
I'd say three weeks to really enjoy the trip. I break a trip like that into two parts. First is the time just to cruise it, days moving. Estimating 500 to 600 nm and saying 60 nm per day cruised, then that's 8 to 10 days. Now I want to only cruise every other day, enjoying the off days at the great locations along the way, so I double that. For the trip to truly be enjoyable, I'd want 3 weeks or very close to it. That will give time in Fort Myers, Naples, Venice, Key West, Key Largo, Miami, Fort Lauderdale, West Palm, Stuart, and on the Okeechobee and other stops you may choose. With less time, I'd just cruise along the west coast where there are many great places to see.
There's little point in just cruising without stopping to enjoy the towns, sights, restaurants, etc. I agree that you'll want at least three weeks to make this a worthwhile trip.

If you don't have three weeks, cruise north or south from Fort Meyers and return.
2 weeks minimum, 3 weeks to enjoy.
You don't want to get just in and out of an anchorage or marina every day and at trawler speed, your itinerary takes a week of sailing.

Now, why go to the East coast? Once you get in Stuart, you have a couple of miles of ICW then one or two days in what we call the canyon, sailing between high rise buildings, traffic, bridges, no fun.
Go slowly down from Ft Myers, explore Naples and the Keys on that side (many anchorages) and come back in one day outside.
One common mistake we all make, and especially when relatively new at it, is trying to go too far or to too many places in one trip. Every place we go has several days worth of attractions and sites to experience and see. We can't see it all the first trip but at least get a good taste and to me that requires at least a one day layover there.

Arriving somewhere at 5:00 PM and leaving at 7:00 AM is pretty much the same as not going there. It's like all my business travel. I traveled everywhere but saw nothing. A long list of places I only saw the airport and another long list of going to a meeting or office, to the hotel and back to the airport.
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