I'm thinking of a trip to SRQ in June/July/August this year for a week or so from MSN to hit the beaches in Siesta Key. I have about 150 hours of TT thus far, 20 or so has been instrument training. The airplane is a PA32-300 with 3 on board including myself. The trip would be conducted under VFR and would remain VFR, and while I will certainly not have my IFR rating by that timeframe, I anticipate having enough training by that point to comfortably get myself out of any unanticipated weather circumstances that may arise, although I'm looking for feedback on that assumption.
The farthest cross county I've flown is into KGRI, which was excellent experience but all flatland flying. I've never crossed anything even resembling mountains, so getting across the appalachians is the biggest thing that sticks out to me about this trip.
Looking for feedback here; things I should be aware of, what to do, what not to do, what to avoid, am I crazy...etc etc.
You're not crazy, I absolutely recommend taking this flight, with the caveats below - Long cross country flights are the best way to learn without a CFI aboard, provided you do everything you can to anticipate and learn about things you haven't experienced yet.
First off: Brief your passengers that you're going to keep them safe and that trumps everything else. Do NOT plan on, nor let them plan on, going out to dinner with Aunt Sally at 5:30 PM. You may not get there in one day, or two or three or six. I like to explain it to pax like this: "Aviation is always a great adventure, it just may not be the adventure you had planned on." If you keep a positive attitude about changes to the initial plan, and keep that spirit of exploration rather than focus on the destination or any pre-planned intermediate stops, you will both be safer and have more fun discovering our beautiful country.
Second: If you have to be somewhere by a specific time, leave early enough that you could make it there driving. Get to the airport and you have a dead mag? Drive. Weather drops unexpectedly en route? Land, rent a car, drive. That way, you'll mostly eliminate the get-there-itis that has killed many pilots. So, don't plan to be in Sarasota on day 1.
Third: If you want your passengers to fly with you again, you'd best consider their experience. Just because they don't hurl during turbulence doesn't mean they want to sit through it for hours. They're not aviation geeks, you have to show them that this is a *fun* way to get places or they'll never go on a long trip in your plane again. With that in mind, on a trip like this one, it's best to plan to stop short and overnight and tackle Florida early in the morning. Just because they (and you) can handle Wisconsin turbulence doesn't mean they can handle Florida temps and turbulence in the heat of summer. It can get downright miserable down there even for gung-ho pilots! Flying high will help you stay in cooler, drier air but in Florida in the summer, you're not going to get high enough to get out of the bumps unless you're burning Jet-A. So, find some things to do along the way that your pax will like, stay overnight, and start the last leg of your trip as close to sunrise as possible. Also, keep the legs reasonably short - 3 hours max - And don't fly more than 8 hours in a day.
Fourth: See #1. Plan for flexibility. Choose several different fuel stops based on what winds/weather might do to you, and be prepared to scrap that entire set of plans and make up a new one in the air. To practice the in-the-air part on the ground, turn your tablet into airplane mode and limit yourself to that information, because that's what you'll have available.
Now that the caveats are over, a few hints:
A) Do some sightseeing on the way (remember that whole passenger experience thing). Looking at where I think you're coming from roughly, and where you're going, I'd suggest you do some extra planning and go down the Chicago lakeshore. It's a cool sight. I'm sure others will have some suggestions farther south if you ask. Consider things your pax might want to see on the ground, too. Example: If they're into cars, a stop in Bowling Green, KY to go to the Corvette Museum. Focus on their interests and see what you can find. On the trip south, it's good to take a break in the afternoon to avoid the heat and bumps and do something fun in air-conditioned comfort before taking off again closer to sunset. If you time it right, you can fly over some of the more boring parts of the landscape at night too.
B) Learning to fly in the Midwest, you may have been told to avoid dark fields in an emergency because they're freshly plowed and you can easily dig in and flip over. (Or not, since plowing fields isn't considered the best practice agriculturally any more). In Florida, go ahead and go for a dark field - Down there, it's sugar cane and the dark ones have been burned and are clear.
C) Have fun!
One note on forum etiquette-- It's better to title your thread "Wisconsin to Florida" rather than "KMSN to KSRQ". Folks who know where SRQ is might not know where MSN is, and vice versa, forcing them to look it up. I can remember a lot of airport identifiers, but not all of them. Raise your hand if you're not from the Midwest and knew where GRI was?
I learned to fly at KMSN (Madison, WI) so I knew that one. I've flown into Sarasota (KSRQ) so I knew that. Without looking, I'm guessing KGRI is Grand Island, NE. I've probably traveled around the country more than most, though.
For some reason I can remember/figure out airport codes like nobody's business, but I can't remember people's names to save my life.