For Florida, I've been to Orlando, Sanibel, Siesta Key, Cocoa Beach, St Augustine, but it's all been 10-15 years ago when my kids were Disney age. I've seen enough to know that I prefer the gulf side.
Sanibel and Siesta Key would be good, but just a matter of finding some place at a reasonable rate.
I've played the links and Baytowne courses @ San Destin. Beautiful.I've stayed at this resort in Sandestin FL.
Hilton Sandestin Beach Golf Resort & Spa | Destin, FL Beach Resort & Spa
Recently stayed at the Wyndham resort in Clearwater with the GF. She got the room on the 14th floor through her timeshare. The advantage here is you can fly into Tampa airport, rent the car, drive across the bay, and you are there.
Clearwater Beach Hotels | Wyndham Grand
A few pictures I posted in my thread.
They even have free beer at the checkin counter. If you bring a insulated cup, they will fill it. This picture was "the moment." Drink in my hand, was drinking my own beers I brought down, and the pool waiters didn't care. Went to Busch Gardens, and drove 2 hours over to Orlando to visit Sea World. Many restaurants, went to Mellow Mushroom and a Falafel place next to Busch Gardens.
It was fancy, but maybe you can book your stay Monday through Thursday to save money.
You can use Maps.Google.Com and look at all the resorts on the beach at Clearwater for prices. If you go just south of the Wyndham they drop in price, and it depends on when you go. Look at where hwy 60 hits the beach at Pier 60 Clearwater. The Wyndham is just south of this. Keep going south and the prices drop but they're not as fancy. The Wyndham would be a splurge, but worth it.
Destin is a bit of a shithole. Horrible zoning. No regrets moving from Destin to Santa Rosa Beach
Ft Meyers Beach is nice if you wanna relax. We stay at Pointe Estero. Its a mile or two from the "down town" tourist trap area that has decent food, bars, bands, etc.
Not a ton to do at the "resort", but you walk 100 feet to the gulf, rent some chairs/umbrella and relax. They have a pool with grills and seating. Do some swimming, wave runner rental if you feel like it. This building is condos and in our experience (3 times now) look good and are well maintained.
Hoping to buy one in the next 10 years when we get closer to retirement. Place to vacation and generate income.
Pointe Estero Beach Resort | Official Site | Fort Myers Beach Hotels
All depends on what you are looking for. Tampa/Clearwater area has a ton more options, but also more people.
Where do you live in Wisconsin? Flights out of Chicago ORD/MDW are plentiful and cheap. I assume MKE has less flights and might not be as reasonable cost wise.