How to plan the perfect road trip

With the rise in WFH culture allowing for some new-found flexibility, a slower approach to travel could be on the up. The past year has also generated a keener appreciation for the great outdoors, so a journey that’s as key to the experience as the destination itself seems particularly appealing. “Road-tripping is one of the best ways to travel on your own time and at your own pace. I love that you get to decide when and where to stop, what to eat, and who you meet up with along the way,” says travel photographer Tiffany Nguyen. Not having to rush makes for an idyllic trip, so give yourself as much time as possible.

With far-flung vacations less possible right now, road trips lend themselves particularly well to staycations and provide the opportunity to explore places much closer to home, too. You don’t have to worry about packing that flashlight when you’re not beholden to cramming every item into hand luggage, either. The essentials? “Snacks, good company and a solid playlist,” advises Nguyen.

One of the most exhilarating elements of road-trip travel is getting to grasp the geography and landscape of a place. “The main reason I love road-tripping is that I feel I really get to see a destination,” says Holly Rubenstein, writer and host of The Travel Diaries podcast. “Too often, travel involves heading straight to a hotel and barely leaving. Road trips show you the tapestry of a place, and allow you to spontaneously discover some true hidden gems. And having the flexibility to pull over at any time for photo opportunities is an added bonus.”

While mapping out a general route ensures you’ll get to all the places you’re desperate to see (and that you can book accommodation, if you’re not keen on winging it), keeping things relatively flexible is the beauty of road-tripping. “I am often guilty of over-planning travel but, when it comes to road trips, I plan the broad brush strokes – the key stops, sights I don’t want to miss, some reservations,” says Rubenstein. “Then, if you’re smitten with a certain stop, you can stay on a night or two longer without too much worry – or drive through a destination altogether if you're not feeling it.”

Nguyen concurs that a degree of spontaneity is paramount, even if it means overriding your itinerary instincts. “I’m very much a planner, but I always leave time for unplanned stops along the way,” she says. “It’s important to be prepared and plan ahead of time, but you really only have control over so much. Some of the best moments happen by being spontaneous, so I always leave some breathing room in the itinerary.”

While road trips don’t have to be seasonal, factoring in when the scenery will be at its most spectacular makes for an even more magical expedition. For Rubenstein, this meant driving from Toronto to Manhattan, stopping at Niagara Falls, the Finger Lakes and the Catskills in Upstate New York during fall, when the trees were ablaze in oranges, reds and purples.

“Not only did we tick off a bucket-list experience at Niagara Falls, we fell in love with a whole region of New York State beyond the city. In the Finger Lakes, we found magnificent, far-stretching lakes (there are 11). It’s the East Coast’s wine country, full of vineyards and charming inns,” she says of her favorite ever road trip. “A scenery of forested peaks dotted with waterfalls led us down to the Catskills, with its quaint villages and hipster hotels. It was the perfect blend of two fantastic cities with the best of rural USA.”

It was also the fall colors that captured Nguyen on a trip through northeastern US, which is known for its road-trip desirability. “We explored five different states in just one week and saw some of the most incredible colors I’ve ever laid eyes on,” she says. “Growing up in California, I had never seen so many different shades of yellow, orange and red during autumn. Each state had something unique to offer – and being able to see it all during the peak of the season made it even more memorable.”