When Driving Beats Flying, Trains, and Cruises: Hagerty’s Travel Breakdown

At Hagerty Media, we love driving—but we also know when other travel options make more sense. Air travel covers more miles per minute, trains can be relaxing and cost-effective, and cruise ships offer buffets you won’t find in most cars. Still, we wondered: when is driving the smartest choice? Our team weighed in.

Family Travel: When the Road Rules

Ben Woodworth on Kids, Geography, and Mountain Bikes

"When you have 4 kids and can’t afford to fly… but aside from the kids thing, it’s geographical for me."

Woodworth drives anywhere along the coasts or between the Pacific and the eastern edge of the Rockies—even as far east as South Dakota if he’s passing through the Black Hills or Badlands. But he draws the line at crossing the plains. "Been there, done that… like 20+ times." He’d rather fly over them. The exception? Mountain biking trips—"In which case, it’s drive every time."

Woodworth’s childhood in a two-tone Dodge Maxi Van taught him the value of road trips. Today, he credits screens for saving long drives with kids: "As much as I hate to admit it, screens are the best thing to ever happen to long road trips with kids!"

Greg Ingold: No TSA, No Stress, Just Open Roads

"I will always prefer driving to other modes of transportation. There is no better way to see this vast country we live in."

Ingold loves planning side quests and appreciates the lack of airport hassles. "It’s also less stressful than flying, dealing with TSA, connecting flights, etc."

When to Skip the Wheel: The 10- to 12-Hour Rule

Jordan Lewis on Decompression vs. Efficiency

"My cutoff for flying rather than driving is probably when the most efficient road-trip route hits the 10- or 12-hour mark per day."

Lewis finds drives under 10–12 hours relaxing—ideal for music, chats, or scenic detours. But once trips require fast-food drive-throughs, toll roads, or cramming lunch and dinner into tight windows, they become more endurance test than pleasure. "In that case, I welcome the (relative) efficiency of flying."

Key Takeaways: Hagerty’s Travel Guidelines

• Drive if: You’re traveling with kids, exploring coastal or mountainous regions, or prioritizing flexibility and sightseeing.
• Fly if: Your route exceeds 10–12 hours of driving per day, involves tedious toll roads, or demands fast-food marathons.
• Consider trains or cruises for long-distance comfort, dining, or when driving isn’t practical.