William Steinberg, Vice President, on Planning the Perfect Road Trip

As William Steinberg highlights, hitting the open road offers a unique kind of freedom that few other forms of travel provide. Whether you’re planning a weekend getaway or a cross-country adventure, a well-thought-out road trip can be both relaxing and thrilling. From choosing the right route and setting a budget to packing efficiently and staying safe, every step plays a role in shaping the experience. Flexibility is key, as some of the best moments come from the unexpected turns and stops along the way.

Choosing a Destination and Route

Start by thinking about how far you want to drive and what kind of places interest you most. Some prefer coastal drives and ocean views, while others are drawn to mountain towns or historic landmarks. Consider how much time you have and what the season offers—some routes are more enjoyable in summer, while others shine in the fall.

Once you’ve narrowed down a region or theme, use apps such as Google Maps or Roadtrippers to sketch out a route. These can help you spot scenic detours or roadside attractions worth visiting. A good road trip balances destination goals with flexible timing. You might find a hidden gem like a local diner or scenic trail that wasn’t on your radar. Add in a few planned stops where you can stretch, grab food, or briefly explore a new area. This helps break up long drives and keeps the experience enjoyable rather than exhausting.

Setting a Realistic Budget

Before hitting the road, it’s smart to outline what you’re willing to spend. Factor in all the basics—gas, meals, overnight stays, and any activities you plan to enjoy along the way. Costs can add up quickly, especially if you’re traveling through areas with higher prices or staying in popular tourist towns.

Many seasoned road trippers set a daily allowance to help keep spending in check. It doesn’t have to be exact down to the dollar, but having a ballpark figure can help you avoid surprises. Keeping a little extra on hand can also come in handy if you decide to splurge on a special meal or unexpected event.

Getting the Vehicle Ready

Before starting any long drive, make sure your car is in good shape. A quick check-up can prevent major issues down the road. Things like tire pressure, engine oil, and brake condition are small details that make a big difference when you’re covering hundreds of miles. Don’t forget to check windshield wipers and fluid levels—those can come in handy during sudden weather changes.

Taking the time to pack an emergency kit is equally important. Toss in jumper cables, a flashlight, and basic tools, so you’re not caught off guard. Some travelers also like to have a roadside assistance plan for added peace of mind. A well-prepared vehicle not only keeps you safer but also makes the journey smoother from start to finish.

Packing for the Road

Packing smart makes a big difference, especially on longer trips. Start with the essentials—license, registration, insurance, and any documents you might need for accommodations. It’s also helpful to bring a phone charger, sunglasses, and a reusable water bottle for convenience. A printed copy of your route can be a good backup in case your phone loses signal.

The weather can change quickly, particularly if you’re crossing different regions. A lightweight jacket, a raincoat, or extra layers might save you from discomfort later. Some travelers like to bring a small cooler stocked with snacks, drinks, and items that don’t require refrigeration. Keeping the car organized helps everything stay within reach without creating clutter.

Long stretches behind the wheel can get dull, so a few in-car activities go a long way. Audiobooks, playlists, or travel games can keep everyone entertained, especially if you’re driving through remote areas with spotty service.

Planning Where to Stay

Deciding where to sleep each night can shape the tone of your journey. Whether you’re into rustic campgrounds, charming bed and breakfasts, or reliable hotel chains, try to book ahead if you’re headed somewhere popular. That extra bit of planning saves time and helps avoid last-minute stress when you’re tired from driving. Some travelers enjoy mixing it up—one night under the stars, another in a cozy inn.

Using trusted travel websites or apps can provide real-time availability and reviews from other travelers. If flexibility is part of your plan, having a few backup options noted can be a real lifesaver if your first choice is full or not quite what you expected. It’s also worth checking cancellation policies in case plans need to shift mid-trip.

Staying Flexible and Safe

While it’s great to have a plan, leaving room for spontaneity often leads to the most memorable experiences. A roadside fruit stand, a scenic overlook, or a quirky local museum might not be on your itinerary, but can become highlights of the trip.

Improvisational skills can be invaluable on road trips. During one cross-country trip  from Virginia Beach, VA, to Los Angeles, CA, I got caught in a sudden snowstorm just outside Albuquerque, NM. Luckily, an 18-wheeler came along, and I was able to tuck in behind it and follow safely into the city.

Safety should never be an afterthought. Let someone know your route ahead of time and check in when you can. Keeping emergency contacts and roadside assistance details saved on your phone helps you stay prepared without feeling anxious. Having a first-aid kit within reach is also a smart move, especially if you’re traveling with kids or pets. With a little foresight and a relaxed mindset, you’ll be ready to enjoy the expected and the surprises along the way.