The only places in Florida I’d recommend are the obvious ones. But if you have your choice of beaches for a leisurely beach vacation, I’d pick Sarasota as it has the best, whitest beaches. I don’t even like the beach and even I have to admit they are nice.
Unless she has a tendency to get carsick. I took a helicopter ride in the Grand Canyon, and my clearest memory of it is that people who get motion sick should not take helicopter rides in the Grand Canyon. I think the idea is that these are supposed to be enjoyable experiences.
When you hit NJ, you should go to the Grease Trucks in New Brunswick. Speaking as a native, there isn’t much else here worth doing (unless you like beaches; I’m told we have some lovely ones). That being said, “spectators see more of the game”. I’m sure there are some good tourist attractions here.
Florida has…beautiful clean beaches on the west coast.
Disney World in Orlando.
Giant shopping malls, like Sawgrass Mills in South Florida.
Old forts and such in the Spanish Quarter, near Jacksonville.
Nightclubs and celebs in Miami.
Laid back island lifestyle in the middle keys.
Wild and wacky lifestyle in Key West.
Do it all! It only takes 10 hours to drive the length of the state, if you go all the way to the keys… 
-D/a
This is a great thread with many really valuable tips in it.
That said, I have a bit of a dissenting opinion about your plan. I base this on my Father’s experience with going to all 50.
My Dad got his last state a few years ago, he’s in his 60’s now. It started off as him just getting around a lot, and then formed itself into a game. He had hit many states that tourists don’t visit being from Iowa, and was stationed in Hawaii during Vietnam.
As kids we heard of his travels, and his goal of seeing all 50. That was a big thing for him, or at least a goal he was looking forward to pursuing. He did it, and he loved it, but he was 60+.
Layovers do NOT count. This is a life experience, not a quick “tick off the boxes” game. A significant photo would be a good reminder, nothing too monumental, but more than the airport in Delaware.
She is not yet 4, and will remember next to nothing about some of your trips. Photos are good, real memories are better. Do her a favor and get the least favorable states out of the way (I’m looking at you Idaho), but leave the gems for when she’ll remember them in a significant way.
My Dad put a lot of effort into seeing all 50, and half of his pleasure upon completing the feat was in the journey’s themselves.
Don’t play the whole game for her and then give her the controller for the last hit on the last boss. The journey is the reward, not the achievement medal.
I’ll second this, with the added suggestion that you delay this trip until she’s in her teens. Then you can take her for a ride along the lakefront in Chicago and she can go home and tell her friends that her parents had her on LSD on vacation.
Lake Shore Drive
It’s also a seriously beautiful drive.
The object of Four Corners is that it’s just a spot on the ground where the 4 states meet, in the middle of nowhere. You’re going to the spot, and there’s no breathtaking gorge or canyon or snaking river, it’s just a survey benchmark on the ground in the middle of a barren high desert. Personally, I think that’s cool - hey, I’m easily amused - and I’d go back (I was there many years ago, as a child). You have to set your expectations appropriately.
If hawkers set up their booths to sell their wares, so be it and I’d just ignore them to get to The Spot.
It’s like the Southernmost Point in the USA. On the mainland it’s in Key West and it’s a pretty place. There’s a fancy marker and it’s a cool place to get your picture taken. But in all the 50 states it’s on the big island of Hawaii and there’s nothing there, barely even a marker or small sign, and just a barren, jagged cliff on the ocean at the end of a 7-8 mile lonesome road. It’s hardly worth a picture. Still, geographically they are notable places and I enjoyed going to both.
Ya gotta do your homework before you go. A quick image search is a quick way to set expectations:
[ul]
[li]Four Corners Nat’l Monument[/li][li]Southernmost Point of states 1-49: Key West FL[/li][li]Southernmost Point of states 1-50:, Hawaii[/li][/ul]
You can easily get Virginia (my home state) and Maryland in a single trip to Washington DC, which has a ton of great tourist stuff to do (museums, monuments, etc.) and should be on your list at some point, even if it isn’t technically a state. Sticking to the general DC area, you could visit Arlington National Cemetary in Virginia as well as the homes of a bunch of historic figures with Washington’s Mount Vernon, Robert E. Lee’s Arlington House (on the grounds of the cemetary) and Jefferson’s Monticello (if you don’t mind a driving a little farther out) all being in the general area. Going a bit farther south, Jamestown and Colonial Williamsburg might be interesting if you’re into history. I haven’t been to either since I was a kid, but I would really like to some time soon.
ETA: A trip up to Pennsylvania to see Gettysburg would also play into the historical site theme and would bump another state off the list.
If you’re into amusement parks, Virginia has a couple of really good ones. Kings Dominion in Doswell, VA (about 1.5-2 hours south of DC) has a huge number of rides including 14 different roller coasters and a full water park located on site. Busch Gardens in Williamsburg is a much nicer park in terms of atmosphere and appearance, but doesn’t have as good a selection of rides (though there are some really good ones and there’s still plenty to do if you’re there for a day or two.) It has an associated water park nearby called Water Country, USA, but it’s a different location and requires a separate ticket.
I’m not as familiar with what Maryland has to offer, but Baltimore does have a great aquarium with lots of other stuff to do around it at the inner harbor.
If you’re ever going along I-94, you could stop off New Salem for a few minutes.
The aquarium is really good, and the inner harbor is interesting. However, there are other things to do in the state. Annapolis from what I’ve seen is quite interesting and has a lot to see that you might not get from other capitals. The Chesapeake Bay is right there and if you like seafood there’s plenty.
I’d also suggest Frederick, which is about an hour north of DC. There’s a lot of history, especially the Civil War, the downtown area is nice, and it’s right at the start of the mountains so there are plenty of places to hike and camp.
Also in Western Maryland you can do Deep Creek Lake, which is nice during the summer, though it can be expensive.
If just looking for a daytrip, Johnson Shut Ins State Park is great time, especially for a kid who likes to climb and play in the water.
If able to spend a couple days go on a float trip on one of the two rivers of the Ozark Scenic Riverway (Current & Jack Forks Rivers). Lots of riverside caves to explore, and the state’s best wildlife (there is a herd of wild horses that live between the rivers).
Cape May at the foot of NJ.
Gorgeous place with lovely beaches and brightly painted Victorian houses everywhere:
Wildwood is ten minute drive up the road. The boardwalk there is just as nice with lots of fun games and an amusement park directly on the beach.
The Wildwoods also have their own type of delightful architechture known as the Doo Wop hotel:
From the time I was a baby my parents drove for vacations. They never actually set out with a goal of reaching all the mainland US states but by the time I was 11 and the end of our “Fly to California for Christmas” trip I had been to at one time or another all US states except Hawaii, Alaska and Washington State. When a chance business trip knocked off Washington and Alaska it kind of intesified my goal of reaching Hawaii.
Basically I don’t think that doing a lot of this while she’s young invalidates the experience but one thing I regret is that my parents didn’t document it very well. I’d love to have an album specifically with pictures of each state. One of the national park passports to collect stamps for every national park is another option.
LavenderBlue has some great Jersey recommendations, but don’t discount the central Jersey beaches either. A day in Point Pleasant or Seaside can be a blast for a ride-age kid.
And as an aside, you damn well better not think about bringing that kiddo into our neck of the woods without coming over for dinner.
Munising (in the UP) is fun. It’s like a whole town stuck in slow motion. If you need time to relax, that’s the place to do it.
In Texas, the Menil Collection if you like art. And just take a walking tour from there, forget your car. Hermann Park and the zoo are both awesome, MFA and the science museum are on the way. But do wander over to the Rice campus on a Friday afternoon and seek Valhalla, the semi-secret Rice drinking hole.
There you have it, a whole awesome Texas vacation totally on foot. Who would have thought it possible?
Yes, Sleeping Bear Dunes, Silver Lake or Charlevoix / Lake Charlivoix is where it’s at. The beaches along the upper west half of Lake Michigan are so nice, especially if you prefer sunsets to sunrises.
Lake Huron, the waters dont seem as clear or blue and the beaches more stoney. There are exceptions though, and great places to snorkel/scuba if you love shipwrecks.
Mackinac Island is known for their fudge. It’s good fudge, but other than that, it’s nautical and quaint, touristy and, well, kinda boring. Not Frankenmuth boring, but still – watch out for the horse shit.
I want to visit Pickax and Brrr and enjoy a vacation 400 miles north of everything … 
[I just finished scanning my 21 The Cat Who books, now I need to look around for the rest]
Take I-77 South and stop in Parkersburg, WV at Blennerhassett Island Historical State Park. Continue South on 77 through scenic WV and cross over into VA right near Rocky Gap where you can make a stop at the Wolf Creek Jewelry Studio.
I-77 and Scenic Highway US 52 run roughly parallel to each other alot of the way through Virginia. You can travel a bit of it then get back on the interstate pretty easily. After you cross over the NC border on 77 South, take a slight detour over to Mt Airy by going East on 89. Mt. Airy is the town Mayberry was based on and the home of Andy Griffith. Leaving Mt. Airy, take 52 South to Pilot Mountain State Park. Hanging Rock State Park is just a short drive East from Pilot Mountain and is scenically superior, so if you have time, check it out too, then get back on 52 South and head to Winston-Salem where you can tour Old Salem and get some Moravian cookies.
After Winston-Salem you can take US421 West to Boone if you have some time to see a few more sights in NC. From Boone, you can go South on 221 and stop at Linville Falls, Linville Gorge and Linville Caverns then get on 40 East back to 77. If you need to get going, you can take Hwy 8 South to Lexington and get a barbecue lunch, then take 85 South back to 77. You’ll go past Concord Mills - a gigantic shopping center where a stop at one of the largest Bass Pro Shops is a must. They have a gigantic freshwater aquarium and stuff for pretty much everything you can do outdoors. Even boats. And RV’s. Place is huge. Anyway, down a little ways off that same exit is Lowe’s Motor Speedway.
Just South of Charlotte, you’ll cross into SC. I don’t know much about SC other than the coast, so my recommendation would be to get on I-20 East and take that over to Florence and make your way over the 501 South and take that straight into Myrtle Beach. There’s lots to do there. Shopping, shows, dining…and there’s a beach too. Then you can meander down US17 to Charleston where there are lots of historical sites. As you work your way down the Coastal Highway (17), you’ll cross over into GA and can make another stop in Savannah. Lot’s more historical sites to see and food to eat! After Savannah, I’d take I-16 back West to I-95 and get the heck out of GA.
Take 95 South till you can get off on Hwy 16 East. Take that over to St. Augustine. There are a ton of state parks in the area, and a Ripley’s Museum. Eat at A1A Aleworks, then take a walking tour of the Castillo de San Marcos and putter around the boutiques. There are a whole lot of interesting historical sites in the area. You can stay the night in one of the many B&Bs. It’s worth a drive South on the A1A to the Fort Matanzas National Monument. It’s the oldest fort in the US. You can keep going South on A1A to Palm Coast where you can hop back on 95 South. If you are inclined, you can make a stop in Daytona Beach. If not, hang a right and head West on I-4 and make a beeline for Orlando. Plan to stay a few days at Walt Disney World.
After that I’d probably be pooped and ready to head home. You could always keep going South and visit Miami and the Keys then head back up the West Coast of FL and visit Tampa on your way home on I-75 North. You’ll get to see some of Tennessee and Kentucky before getting home. I’ve never been to KY, so I have no clue what to see there, but you’ll pass not far from Gatlinburg, TN on that route. It’s a nice area with lots of shops and Dollywood is nearby if you are inclined.
Send me lots of pictures!
Hawaii
Volcanos national park, waipio valley.
Maui
Haleakala crater, the road to Hana.