Drive from Miami to Key West
One of the coolest drives in America, the Oversea Highway(aka the southernmost section of US) stretches 113 miles over 42 bridges(including Seven Mile Bridge) across all of the Florida Keys. Once you get to the Southernmost point in Key West (there is an actual “point” you should selfie next to, duh). snag slice of Key lime pie at Blue Heaven and drink you way down Duval St. This is all after you have partied your face off in South Beach, of course.
Watch NASCAR at Talladega
Better yet, rent an RV or pitch a tent in the North Park and spend the whole weekend there. It is totally free and means you will be hanging out with more than 100,000 of your all-time weirdest friends.
Visit the Alamo in the San Antonio
Remember learning what a big deal this battle was in social-studies class? Sure, it might be just a building that some find disappointing, but this pivotal part of Texas and American history is still worth seeing, and after you do, head over to the pedestrian-only River Walk (you know, that tourist-friend stretch you see during every Spurs home game on TV) and enjoy the bars and restaurants (Pearl Brewery = yes). Now, if you really want to go native – spend a weekend bight at the Cowboys Dancehall. Is it a dancehall? A rodeo? A concert hall? Boxing venue? A place with lots of beer and mechanical bulls? Yes, All of that. Texas forever.
Drink a mint julep at the Kentucky Derby
Preferably several, from the infield. While(non-ironically) wearing seersucker or a fancy hat. Not on the same day(be smart!), but you also should not leave the state without hitting a few of the distilleries on the Kentucky Bourbon Trail.
Eat a PB & Banana toastie at Graceland
Revere the King in all his glory with his favorite meal at his massive estate in Memphis. (Not that he is really dead, of course.)
Tailgate at the Grove at Ole Miss
Honestly , you can not go wrong with pretty much any SEC tailgate(unless it is Vanderbilt), but few school throw the kind of pre-game party like you will find at the Grove. You should also probably sit in the student section for the game. Alternate venue: if for some reason you are like, no way I am going to O xford, I do not care if it is Faulkner is hometown and that it has that really cool three-building bookstore, the Auburn-Alabama Iron Bowl in Tuscaloosa is your move.
Stroll the French Quarter in New Orleans
Must-stops: Cafe Du Monde for a beignet, Pat O’Brien’s for a Hurricane. (Bonus points if you also attend Jazz Fest)
Hang out in Austin NOT during SXSW
Experience Austin in all its true weirdness by avoiding the massive nerd convention and doing it up like the locals. Rather than make time for it all, concentrate on stuff like a breakfast taco tour, a dip in Barton Springs, and BBQ at one of these highly touted places(because no local waits in the massive Franklin line).
Spend a day in St. Augustine
The oldest town in the US (1565) is actually good for something other than eight-grade field trips. In fact, it is so great we named it Florida’s most underrated destination. After getting your fill of colonial Spanish architecture, spend the day deep-sea fishing, and the night bar-hopping /taking a haunted bar tour in the historic section of town.
Catch a game at Wrigley Field
The fact that the Cubs are actually – gasp! – contenders now only makes this epic sports pilgrimage that much better. Shoot foe a Cards game, sit in the bleachers, and drink Goose Island while taking down a Chicago-style hot dog. After the game, enjoy a beverage or two at the bars around the stadium Wrigleyville is not known as the “world’s largest beer garden” for nothing.