I've Traveled Over 400,000 Miles With This Away Carry-On—Here's How It's Held Up

When I picture a road trip, I see images of two carefree people in a convertible traversing Route 66. There are no kids in the picture, and I'm not even sure there is luggage. It feels so easy and inexpensive. A road trip with kids, however, is a different experience, especially when those kids are teenagers.

This as-told-to essay is based on a conversation with Tobi Oluwole, a 30-year-old former sales manager at a Big Tech firm who recently relocated to France. His former employer is known to Business Insider but is not named for confidentiality. The following has been edited for length and clarity.

The holidays are an expensive time of year — especially if you're hoping to travel to visit loved ones or head out on a peak-season vacation.

When you think of destinations that affluent jet setters might frequent, the likes of London, Paris, and New York's Hamptons probably come to mind.

Last week, Hurricane Helene made landfall in Florida as a Category 4 storm before ripping through six states leaving a path of destruction in its wake and killing more than 100 people. The record-breaking storm – which clocked 140 mph winds and a storm surge that reached more than 15 feet above ground in the Florida Big Bend region – has left millions to deal with flooded roads, flattened homes and buildings, and power outages. North Carolina, Georgia, Florida, Tennessee, South Carolina and Alabama have all made disaster declarations as emergency responders work to rescue missing persons and more than 1.2 million are still without power as of Wednesday, according to PowerOutage.us. Popular North Carolina mountain towns – including Asheville – which have become top tourist destinations in the fall, have been reduced to debris as residents are left to rebuild their lives. Carrie Tucker of Charlotte, North Carolina, told Travel + Leisure in the wake of Hurricane Helene, western North Carolina is “completely cut off from life – no roads, no gas, no food.”

Southwest Airlines is giving travelers an extra reason to say “wow” when planning a vacation.  The Dallas-based airline recently announced the «Save WOW» fare sale, with deals up to 40 percent off base fares. Best of all, the sale covers flights through March 2025 to several popular destinations, making it a perfect option for travelers looking for a fall, winter, and even early spring getaway.  The fare sale runs from now through October 3, 2024 at 11:59 p.m.

As a beer aficionado, I've been to my fair share of brew festivals throughout the US, several of which were "Oktoberfest" themed.

In 2019, while on a trip to Marrakech in Morocco, Gary He, a Brooklyn-based photojournalist, received an unexpected surprise with his regular McDonald's order.

I love visiting kitschy or unique tourist landmarks on a road trip or weekend getaway. In fact, after visiting all 50 states solo, I've enjoyed my short visits to nearly all the major tourist attractions in the United States.

When the Van Cortlandt family acquired their sprawling Hudson Valley estate in the late 1600s, they couldn't have imagined that it would one day host a jack-o'-lantern festival with pumpkin sculptures including a Kraken, moving windmill, and Statue of Liberty.

There are plenty of amazing leaf-peeping opportunities in the US. A romantic road trip to see the covered bridges of New England is one, taking an air balloon ride to see the foliage from above is another. But the most relaxed and nostalgic way to experience fall in all its glory is by train. There are multiple vintage railroads in the United States that will transport you back in time while you admire the fall colors, but few do it as well as the East Broad Top railroad.

When my friend Jessie invited me to travel with her to Kyrgyzstan, I wasn't sure I'd be able to find it on a map.