Six Globe-Spanning Road Trips Every Gent Should Conquer

Ever done Italy in a Maserati? Because you should.

By Kirk Miller

Six Globe-Spanning Road Trips Every Gent Should Conquer
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26 May 2017

This is just one installment of 37 Things a Man's Gotta Do This Summer, our annual compendium of everything worth seeing, doing, eating, drinking and generally making time for in your neck of the woods between now and September.


First, maybe don’t get away this weekend. Those roads will be packed.

But after that, by all means, get behind the wheel and go off the beaten path. There are natural wonders (and weird, kitschy man-made ones) that need your attention.

To help: our guide to six must-take road trips, spanning both coasts as well as a few stops beyond our borders.

From why you finally have to get your kicks on Route 66 to a Michelin-starred food sojourn, strap in.

You’re in for some wild rides.

Get Your Kicks on Route 66 (While You Can)

According to Skift, the historic 2,500-mile stretch between Chicago and the West Coast might be dropped from a National Park Service funding/preservation program, severely hurting tourist towns along the iconic “Mother Road.” If you want to see true Americana, filled with neon signs, ghost towns and meteor craters (and the Cadillac Ranch), call your Congressperson and hit the road—and use this tool to plan your journey.

Go Foodie

If you were to drive to every Michelin Star restaurant in the country, isn't every stop a memorable milestone — in the literal sense? Orbitz thinks so. Earlier this year the travel site published a map that plots the fastest route between all of America’s Michelin-starred restaurants, and needless to say, it’s a doozy, stretching from San Francisco through New York. 77 stars spread across 68 restaurants and 3,426 miles.

Traverse the Florida Keys

You’re essentially island hopping on crazy long bridges, where you’ll be exposed to a lot of natural beauty, wildlife (mini-deers!) and — since it’s Key West — a damn good party. Also, it’s a short trip (three-plus hours if you don’t stop) and you can stop for scuba excursions, turtle watching and the hard-to-find No Name Pub, which is covered in one dollar bills.

Get Specifically Weird

First, please go to Atlas Obscura to check out their curated guides to the “strangest and most curious places” in the world. Then, use their wonderfully weird suggestions to plot a course: it could mean “A Rat Lover’s Tour of the World” or “15 Unlikely Places to Re-Up Your Luck” (which is mainly Europe). But you could do a crazy road trip across the U.S. this summer revolving around “The Ultimate List of Wonderfully Specific Museums,” which spans California (Pez museum), Georgia (National Tick Collection), North Carolina (tubas!) and Wisconsin (Mustard Museum).

Go Italian

Coined the Prestige & Passion of Italy: Celebrating 350 Years of Italian Racing, this 10-day experience traversing Italy is brimming with fine dining, obviously, but also five iconic supercars behind-the-scenes.From travel specialist Zicasso, the bespoke adventure takes place in the Emilia-Romagna region between Bologna and Maranello, otherwise known as “Motor Valley.” Along the way, you’ll be invited to explore the art of the race car with a trip to Maserati’s gallery with 19 vintage steeds, as well as partaking in five country road cruising test drives with a Ferrari, Lambo, Maserati and Ducati.

Go Your Own Way

Start with your free road planning app (Roadtrippers). Bone up on road trip games that go beyond Slug Bug. If you’re stateside, study this comedic travelogue that decidedly favors the quainter towns of “real America.” If you’re going seriously off-road, listen to this woman. More about two wheels? This is the weekend to go hog wild (if you’re in New York). Or if you’re about bikes, Trek Travel can get you luxury cycling vacations around the globe. Want to base your trip purely around weather? There’s a map for that. Can’t stand the thought of getting behind the wheel? A luxury train ride through Peru leaves the driving to others.

And, uh, don’t go here.

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