Gotta say, I'm pretty envious of your flexibility and the travel it affords you. It's a good place to be in life for certain. Congrats on the work it took to get to this point!
Some boating thoughts.......
If you want a good party, put Harmon Creek on Lake Cumberland during Poker Run Weekend on your list. Like Mardi Gras on the water. Good "scenery" for a young single man. Lake isn't much to write home about otherwise. If you're there on a non-poker run weekend 76 falls tends to have a pretty big party going on pretty much all the time.
Dale Hollow is one of the clearest lakes I've ever been on. It doesn't have that blue/green color the gulf has, but you can see 20+ft down clearly in most places. Not a ton to do on the lake really, but it's a nice place to visit.
We enjoyed Douglas Lake in TN. Nice clear water in a pretty "mountainous" setting. Otherwise, just another lake really. Pigeon Forge and Gatlinburg are very nearby in case you get tired of the water. Neat touristy mountainy setting near the east coast.
Destin and Pensacola area along the gulf has some crystal clear water. Watching the Blue Angles practice from the water was pretty awesome. Crab Island is a neat experience, especially if you have some friends to hang out with in the water and play/snorkel around.
We did Old Hickory Lake to Nashville on the Cumberland River a few years ago. Cumberland River is not that spectacular, but the lake is neat, and the nightlife in Nashville is pretty awesome. There is a marina just south/west of downtown that rents transient slips. Head down by water, slip, grab a hotel and party for the night or two, hop on the boat and head back up river. Have to lock through to get between the lake and river. Surprisingly easy.
We're taking the boat to St. Augustine in about 8 weeks or so. Be interesting to see how boating there compares to boating around Destin. Had plans to hit Lake of the Ozarks this summer, but the move to NY kind of borked those plans for us. We have a bimini trip on our bucket list, but I'm not sure when we'll make that happen, probably want a bigger boat before we do that.
The big thing with travelling with the boat is finding storage and ramps to use. We've found that a few days researching and planning up front really makes the whole experience MUCH easier. Make sure you have a place to unload/load the truck at the beginning and end of the trip. Then make sure you have a secure place to store the boat, and it has the right amenities for your machine. Adventure Marina in Ft Walton is a great example. They have a secured lot, with fresh water and 120V power available, for a VERY reasonable weekly rental fee. Makes taking the boat south VERY easy.
Good Luck!
