Like a Bible Belt Route 66, U.S. Route 90 is a small-road classic: a 1920s-era roadway that snakes along the Gulf of Mexico, through the beach towns of the Redneck Riviera, southern Mississippi's casinos, and New Orleans, until it ends in the Texas desert. The best drive is on the 150-mile stretch from Mobile, Alabama, to New Orleans.
1. Start in Mobile, which looks like a low-key New Orleans – same shotgun houses, but with fewer bars and no one trying to be cool – then hit the road as fast as you can.
2. Dauphin Island, a spit of land in Mobile Bay, offers clear Gulf water and broad, white-sand beaches, without the crowds that overrun the Redneck Riviera. Get one of the seafood shops to fix you a boiled-shrimp lunch for a beach picnic or check out Fort Gaines, which dates to just after the War of 1812. In late August, if you hear a cannon blast, relax: They're reenacting the Battle of Mobile Bay.
3. Gambling has turned the Mississippi Gulf Coast into a mini-Vegas, so play cards if you must, or just drive, water to one side, antebellum mansions shrouded in centuries-old oaks to the other. Stop for gumbo or oysters. Hardier folks will opt for a camping trip on Deer or Horn island, which are empty and wild. Fish, swim, and pray the offshore breeze keeps the heat down and the mosquitoes at bay.
4. From the Mississippi border into New Orleans, 90 dives into the Louisiana swampland. Narrow roads twist away to ramshackle fishing camps and decaying shrimper marinas. Enjoy the marshes, hunt for alligators on a swamp tour, or just hustle for New Orleans.
5. All the touristy New Orleans things – étouffée at Dooky Chase's, a po'boy at Domilise's, or jazz at Snug Harbor – are still worth doing. But you might try an underground, back-alley restaurant like Pizza Delicious, in the Bywater. Afterward, you could check out a "bounce" party or head to the all-vinyl "mod dance" at the nearby Saturn Bar. Just remember to park the car first.
Getting There: Mobile Regional Airport is only 20 minutes from U.S. Route 90. On Dauphin Island, Skinner's Seafood has fresh-caught crab and shrimp. Camp on Deer or Horn Island. Pies at Pizza Delicious in New Orleans are $13 to $20.