How to Plan the Perfect Road Trip

Every car enthusiast dreams of the ultimate road trip: winding roads, stunning views, top-tier accommodations, and unforgettable pit stops. But crafting that kind of experience takes more than Google Maps and a playlist. 

That’s where someone like Asa, the mastermind behind Crown Rally, comes in. We sat down with him to learn what goes into planning the perfect driving adventure. 

Exploring the back mountain roads of New England

The Art of the Route: It’s About the Drive, Not the Destination

For Asa, the route is the experience. Every mile is hand-picked for scenery, flow, and fun.

“The first qualifier is that it should be paved,” Asa says. “We aim to only drive on beautiful paved roads, although many times the GPS and road signs have other ideas.”

Winding back roads far from traffic and towns is the goal. “The windier the better. Straight roads are fun for a little, but the real fun is on the windy roads in the middle of nowhere, with no houses or businesses around.”

Some of his favorite roads don’t even have names—just happy accidents found while scouting. “Back of the Dragon and Blue Ridge Parkway are amazing. The Tail is fine, but after doing it once, I’m over it. I’d rather go and drive on other roads.” After several trips to the overly crowded Dragon, I completely agree.

But great roads aren’t enough—they have to fit. “We need to combine the above factors with the timing of our day, and that is our recipe for success.”

It’s this blend of route quality and perfect timing that makes every Crown Rally feel unforgettable. Of course, we also want to ensure we are taking routes that are safe for our drivers and heavily discourage high speeds or illegal driving behaviors. 

Five-Star Stops: Hotels and Food That Match the Vibe

After a day of adrenaline on the road, where you rest and recharge matters. Crown Rally and Squad Driven isn’t just about driving—it’s a full experience, and that includes high-end hotels, great meals, and smooth logistics. To get it right, Asa does the legwork—literally.

“I do an initial visit 6 to 8 months prior to the rally to book hotels and make sure they are to our standards,” he says. “Then I do a ‘dry run’ about 1–2 months before every rally to cross my Ts and dot my Is with all of the routes, venues, and meals.”

It’s not just about picking luxury spots—it’s about making sure they work in the real world.

“Yes, absolutely,” Asa says when asked if he’s ever rejected a hotel. “This happens more often than you would think. Sometimes the hotel is not as pictured, sometimes the parking situation is a nightmare, sometimes the surrounding area is not walkable or good for our group.”

It’s why in-person visits matter. From parking layouts to neighborhood walkability, Asa takes nothing for granted. And that hands-on approach means rally drivers never have to worry about whether their car—or their comfort—is in good hands. I have traveled with several groups where this hasn’t been the case, leading to expectations that weren’t met, logistical nightmares that hold up the entire group, and some pretty bad food experiences. 

These aren’t just chain hotels, either, one of my favorite places we’ve stayed was in Woodstock, Vermont in the late spring. It was an Inn and Resort with a beautiful courtyard, and fire pits with complimentary s’mores where we got to gather around as a group and get to know each other and relax before kicking off the rally. It was easily one of my favorite nights of the trip. 

Beyond the Wheel: Keeping Things Fun Off the Road

Performance driving—even when done legally on surface roads—can be surprisingly exhausting. Staying alert, navigating winding terrain, and pushing your car (and yourself) takes focus. That’s why a great rally needs more than just fast roads—it needs the right mix of exhilarating drives, beautiful sights, and well-timed breaks with group activities that let everyone reset.

“I think of fun activities that people would enjoy,” Asa says. “Overall, as a group, rallies are adventurous, so there is a pretty wide variety to choose from.”

From scenic overlooks and photo ops to surprise detours, private events, or adrenaline-filled side adventures, Crown Rally’s off-the-road experiences are designed to keep the vibe high and the group energized.

These aren’t just filler stops—they’re part of the experience. Carefully chosen and timed, they turn a great drive into a full-blown memory-making event. And after a long day in the driver’s seat, there’s nothing better than stepping out into something unexpected and unforgettable, like the Bonneville Salt Flats for example.

One of my favorite stops we’ve done so far has been a helicopter tour over the Blue Ridge Mountains after an adrenaline-pumping route through the Tail of the Dragon. At a stop in Pennsylvania, the hotel was attached to a historic steel mill where we could leisurely walk to, learn and adventure (and it made from some great pics with the cars, too).

Skip the Hassle—Just Show Up and Drive

I’ve planned several group road trips over the years—and let me tell you, it’s not easy. Coordinating hotels, routes, meals, and people is a full-time job. It can turn what should be a fun getaway into a logistics headache. And that’s exactly why rallies exists.

The point of a rally isn’t just the roads—it’s the people you meet and the places you get to experience together. And the best way to truly enjoy all of that? Let someone else handle the hard stuff.  It may sound played out, but I’ve also met some pretty great people along the way, too, that I wouldn’t have met otherwise.

Asa does everything—from scouting roads to booking hotels to planning activities. Every route is tested. Every stop is intentional. Every detail is covered. All you have to do is show up, turn the key, and enjoy the ride.

So if you want a road trip without the stress, sign up for Crown Rally—or Squad Driven—and let Asa do the heavy lifting. You just focus on the fun. Check out our routes for 2025 and let us know which rally you’re most excited about!