Driving to/in the keys is torture.
Maybe I’m jaded but I have trouble leaving Sarasota for any place in the keys.

Jaded for sure.

I love the drive to and from the Keys. I live right here just north of you and have my whole life, The Keys never get old to me.

Summer holidays and Shootout do not really add anything time wise for me unless I hit KC rush hour. The only that will add any real time delay is an accident or major construction. For the most part, we try to go down for at least 3 nights. Sometimes its 2, 4, 5 or 12 The nice part is we can change our plan/days anytime we want based on our schedule or weather.

You'd have to ask Cashbar about the Florida guy

I used to drive from Columbia SC to Panama City Florida once a month to my condo from 2008 to 2016. I would leave at 5 or 6 am and an get to PC in time for cocktails on the beach. I picked up and hour due to the time zone difference. A 5 hour drive is doable for me but the 8 hour drives are in the past. I am hoping to start my second childhood in three years as I can retire at 56.5 years from the Feds. I plan to keep my lake place in SC but would like a vacations spot. Loto is on the top of my list. Thanks to everyone for providing comps. It gives me food for thought.

GLOC is our retreat. You can see what we started with. Boat dock is right there too. totally enclosed 50x50 2 slip.
Next to no No wake zone idle till I am hitting it.
It is pretty much right at 1 hour door to door to my business in Tulsa. Can you say--- Go up on Tuesday\ Wednesday- drive in a couple days a week from here.
Great Cove neighbors also except they drink Too much
DownFall??? I cant get the Wife to go to LOTO or KW anymore

One hour drive, most people I know have that just to get to work.

That guy has worn out S. Florida so he has to leave town! I'd suspect his friends/connections in the LOTO area are as much of a draw to the lake as the lake itself.

The traffic, trailer parks/t shirt/shell shops just seem repetitive for the whole way south of Key Largo and that is if you made it through Miami unscathed. NFW would I do that trip regularly to a 2nd home unless I had a Cessna 206/Cirrus SR22 to skip that ride. There are some cool places to stop along the way if you are there for the week, not in a rush to get there/back home but how many times can you stop at Robbies or Alabama Jacks while you still have an hour or more to continue driving.

I had a neighbor that was doing the trip 2X a month, leaving at goofy times to try to beat traffic etc. He finally sold his house and bought something on the water in town here. The hours of driving was a chore compared to just spending more money to live on the water full time. Packing the car, putting the kids in the car seats at 4am to drive home and go to work at 9........crazy.

My Father-in-law bought a dozen lots back in the 60's on Lake Huron just east of the Mackinac Straits for $150 a piece. He had 11 kids so over the years some of us bought lots off of him, at a profit of course and built places of our own. I had just sold a business and took the profits and built my retirement home. Best part is that most of my neighbors are family so all the kids have a great time together. When I was designing my place, I knew I would want a garage big enough for the largest single engine performance boat. So I figured I would need 31' inside depth and 11' ceiling, everything else worked off of that. State run Marina is 2 miles down the road and we are in an area that is so deserted that there is never a wait. From my place it's 20 miles to the nearest city by water so going anywhere is a nice ride. Hundreds of islands to explore and water so clean you can see the bottom in 30+ ft. Property up here is still less than just about anywhere. It's a 4 hour drive from home, but so worth it. We have a huge beautiful sandy beach and we can anchor right close to shore.

I have a buddy that leaves St Louis to get down to Rosemary Beach and is thrilled if he can bang it out in 10-11 hours but he leaves in the middle of the night to have the lightest traffic. He probably does it once every other month.