Samantha Brown Shares Her Best Travel Advice—Including Her Hack for ‘Frugal First Class’

Throughout her nine seasons hosting PBS show Places to Love, Samantha Brown has surfed in New Zealand, gone tubing in Costa Rica, and danced in China, yet it’s a road trip through America that captured her heart.

“In my 25-year career, driving the entire Route 66 is the greatest trip I have ever taken,” she told Travel + Leisure of completing the 2,448-mile journey between Chicago and Santa Monica, California. “There’s that sense of accomplishment, but it’s also going in thinking one thing and coming out and being a different person because of it.”

The 55-year-old travel expert admitted that she wasn’t innately drawn to the highway known as the Mother Road, but had done a mini trip down its Illinois portion for Season 7 and was immediately mesmerized. “The history is phenomenal, and there’s such reciprocity with the people you meet along the way—it’s a real connection of people, places, and history,” she said.

So she and her team decided to traverse the entire route, venturing through Missouri, Oklahoma, and Texas in Season 8, and New Mexico, Arizona, and California in the latest season. “Route 66 is a lot more than just a nostalgic joyride—it really is a through line through the highs and supreme lows of history that we’re grappling with today,” Brown said.

She learned about how Black motorists couldn’t just stop anywhere because of systemic racism during the Jim Crow era, and how Native Americans were forced to march out of their ancestral homes in Oklahoma through the Trail of Tears. And what Brown found along the route was a deeper understanding of what the American spirit truly encompasses.

“It’s an immense optimism of resilience and the grit that really shaped and formed our nation’s identity,” the Brooklynite said. “I know these are not optimistic times, so I think it shows people watching that we’re going to be okay. That’s what travel has such a power to do, especially on these big trips where maybe you’re taking on something physically or historically challenging.”

Brown’s three-season trip down the route was timed to coincide with this year’s 100th anniversary of Route 66—and it’s that kind of timing that sets this season apart. “There’s a timing to this season that makes it feel more current, and more immediate,” she said of also highlighting Williamsburg, Virginia, as part of America’s 250th anniversary this year. Additionally, leaning into Americans’ love for Italy, she also took a slightly different approach, focusing on sustainable luxury goods and kitchen tools in Bologna and balsamic vinegar and Lambrusco wine in Modena.

No matter where in the world she wanders, Brown has turned every aspect of travel into a science, and it all starts with packing math. “I think of multiplication, and then addition,” she said. Pants get three wears each and tops get two wears, so on a two-week vacation, she’ll pack four or five pants and six or seven tops—and then add in the outfit she travels in. The challenge comes with deciding on shoes, which she calls “my nemesis.” But she tries to limit it to two pairs in addition to the one she wears en route.

While she realizes compressible packing cubes have come into vogue, she uses her expandable luggage to do essentially the same thing, packing it while it’s expanded and then zipping it down to compress everything.

Another thing she never risks is time at the airport, noting there’s no reason to look at the departure time, and to base everything on the boarding time. She usually arrives two hours before boarding, but when she travels with her crew and all their equipment, there are times they arrive five hours ahead of an international flight to ensure proper time for all their luggage to go through customs. “I have never in my lifetime felt like I had gotten to the airport too early,” she said. “There’s no such thing as too early, but there is too late. All the stress goes away by getting there in plenty of time.”

While many are laser-focused on getting to their destination after they land, she also suggested taking a moment to observe the airport itself. The departure process will likely require the same navigation, whether it involves trams, long hallways, or potential crowds, so it’s an opportune time to make note so that you’re familiar upon return.

Once arriving at the hotel, Brown is all about thinking outside of the box. “One of the greatest hotel amenities is the ironing board because it’s four feet more counter space—and that’s something that I’m always running out of, especially if I’m traveling with my kids,” she said. The device also doubles as an adjustable stand-up desk. So she’ll set it up in a spot with a nice view, put a towel over it so she doesn’t ruin it, and create the ideal workspace.

When it comes to exploring, the first thing that Brown and her husband Kevin O’Leary always do in every destination is go for a walk. “This is my new home for however many days, so we’ll just set out around the neighborhood and see if there’s a drugstore nearby in case we start not to feel well, or see if there’s a place to grab something quick for dinner.” Additionally, she suggested always going to a destination’s main square or thoroughfare—like Champs-Élysées in Paris or Las Ramblas in Barcelona—and using them as jumping-off points to explore the side streets, where the locals are.

Despite all the decades of travel under her belt, Brown still has ways she hopes to improve her own travels. “I want to be able to see the space,” she said, explaining that sometimes itineraries can start to compound, and you get overwhelmed by the pure logistics and lose sight of the moments between. “It’s like when you look up at the planes that are lining up to land in LaGuardia all spaced three minutes apart. I’d like to be a better air traffic control person. The things are gonna keep coming. You’ve got to see the space between them.”