Below, I have copied a discussion from the T&T (Trawlers and Trawlering) mail list, concerning the charter firm of Southwest Florida Yachts, headquartered in North Fort Myers, and cruising suggestions about the nearby waters (including Pine Island Sound and Charlotte Harbor). All these messages were originally sent as replies to a query on the T&T list. There’s lots of good cruising info here, and, let’s not the forget the good people at Southwestern Florida Yachts are a SALTY SOUTHEAST CRUISERS’ NET SPONSOR!
As usual with this many contributors, it was impractical to obtain individual permissions, so I have ommitted all names.

Southwest Florida Yachts has been around a long time and has a good reputation. Some good stops in the nearby area during your charter would be:
1. Ft. Myers Beach, with moorings and a public dinghy dock, then a short walk across the highway (crowded with hotels, restaurants and shops) to the large and very popular beach.
2. Boca Grande, a small ritzy but quaint town on an island witha small anchorage area among the mangroves.
3. Cayo Costa park, accessible only by boat, with a nice protected anchorage, and a long walk across the island to a secluded beach.
4. Also Punta Gorda, St. Pete Beach, Sarasota, etc…..

I have lived next door to Barb and Vic Hanson the owners of Southwest Florida Yachts for 9 years… they are great people and have never heard anything from them or anyone else negative about their charter boats or charter service.
I have lived in the SW Florida area since 1959… it is absolutely great for cruising… favorite area Pelican Bay Anchorage… absoslutely one of the best places to anchor.

We did Offshore Powerboat training aboard a chartered 42 GB with Southwest Florida Yachts a few years ago.
There are lots of nice places to anchor nearby. You have the intracoastal going north and could also go east into Ochochobee. I’m sure SFY can point out a lot of places to go in the area.
We actually made it down to the Keys and had two wonderful nights in Little Shark River at the Everglades.

SW Florida Yachts have been around since forever, chartering both sail and power and I’ve never heard any knocks on them.
The west coast of Florida is a great cruising location once you get used to the idea of shallow water. Great anchorages abound – you can be alone or in a crowd – you choose. Nice city marinas and several world-class resorts. We just took about 10 days and went south to Pine Island Sound where we spent several nights in Pelican Bay, at Cayo Costa Island (Met T&T listee Jay from “Sails” anchored there) followed by three nights at South Seas Plantation.
Great cruise!

They are good people… The boats are clean and in good repair… I recommend them highly… You will enjoy…
But, this is skinny, skinny, water and there are thrills like the MiserableMile, etc. in store where local knowledge is invaluable… Just getting from the dock at SWY to the intercoastal is an interesting trip in it’s own right… Hire a captain for a couple of days, learn the waters and the idiosyncrasies of the buoys where the gulf waters cross the intercoastal waterway, eat lunch at Sanibel Island and see how the other half lives (very well), etc… Come back to the SWY dock the first night or two and eat/drink at the restaurant right there (very good), then go anchor out for a night or two, etc… Learning the ropes first will make your trip memorable and fun…