Following paradisiacal Overseas Highway is a short-term affair
(the drive can take as little as four hours), and great journey to
tack on to a pre-existing plan to hit up Miami
for Art Basel. Rent a convertible car and start in Key Largo, where
the 113-mile-long series of bridges linking the Florida Keys
begins. The starting point of this trip is a top snorkelling
destination, so we recommend booking in a few hours to explore the
shallow reefs at John Pennekamp Coral Reef State Park. From there,
your focus should turn to food. Try conch fritters at Alabama
Jack’s and Iguana Bait beer at Florida Keys Brewing Co., with a stop along Islamorada
for sunbathing on the beach. Your next traverse will be the Seven
Mile Bridge, which straddles the turquoise Florida Strait and the
Gulf of Mexico. This trip’s final destination is Key West, the
former home of Ernest Hemingway and the ideal spot for a couple of
beachy days to cap things off.

Known as the “Mother Road,” Route 66 is perhaps the world’s
best-known drive. Stretching from
Chicago to LA, the road cuts through part of the South, winds
through the Texas panhandle and hits Georgia O’Keeffe’s New Mexican
landscapes before shooting through the deserts of
Arizona and California. More than any other route, the 66
offers road trippers the chance to see a side of the States they
might never be exposed to otherwise. Savour barbecue in Missouri
and stop by the Ozarks, or make a pit stop in Phoenix before the
home stretch to the City of Angels.

Hugging the
Californian Coast, the Pacific Coast Highway is nothing short
of iconic, and a favourite route among bonafide road trippers.
Stretching from San
Francisco to Los Angeles, this 655-mile excursion will take you
from redwood forests to the beaches of SoCal. The number of TV show
hotspots you’ll encounter (think: the Bixby Creek Bridge of Big
Little Lies fame, and Marissa and Ryan’s OC) is a clear marker of
the noteworthiness of this sliver of the US, while the varied views
and gorgeous year-round weather make the trip even more
worthwhile.

A shorter drive for hikers and hippies at heart, the
LA-to-Joshua
Tree route is a favourite track to follow (and not just among
the Coachella set). Rent a Jeep Wrangler and set out from the city
in the early morning with cup holders locked and loaded with
smoothies and cold brew. Make
Palm Springs your night-one destination, stopping for a swim at
the Ace Hotel and cocktails in
The Parker lobby, a retro-esque
celeb hangout built around an open fire pit. The next day, set out
for the second leg of your journey through arid plains until you
arrive at Joshua Tree for a day of stretching your legs. Once
you’ve worked up an appetite hiking, stop by Pappy + Harriet’s barbecue restaurant and music venue
in Pioneertown before heading back to Palm Springs for your last
night. On the way back to LA, a drive-thru for In-N-Out burgers and
fries may well be in order.

This itinerary is one of the best ways to get a wide-ranging
view of the Deep South. Start off among the pastel facades lining
Charleston’s waterfront and head to Savannah, Georgia. Between
samplings of fried green tomatoes, grits and the city’s famous
pralines, make sure to carve out a day or two to check out Hilton
Head Island just off the coast, where, after hours in the car, you
can give your legs a workout on beach cruiser bikes and take
advantage of the bathtub-warm ocean waves. Next, you’ll hit the
South’s holy trinity of music – Atlanta,
Nashville and Memphis – before making your way down to
New Orleans for days of dancing and Creole cuisine.