What to plan and what to wing on a road trip

On the Road 3 min read

When I was 6, my favorite vacation spot wasn’t Disney World—it was Toronto (the subway rides sealed it for me).

Wherever I’ve been in life—a little kid, along for the ride with my jet-setting parents, or an adult with a tight budget—I’ve always made room for travel.

And the great thing about trips is that they can be epic, without an exotic location and unlimited budget, and even if there are a few bumps in the road. (Mishaps sometimes make memories, but now you can get travel insurance to help with the unexpected, too.)

So, from my own experience and others’, here’s how to plan an epic trip of your own, on the road.

PLAN: Your final destination. WING: Stops along the way.

Last year, a co-worker and her husband planned a road trip for their honeymoon and only set one thing in stone: their final destination (Asheville, North Carolina).

A road trip like this is a complete adventure—instead of focusing on how many hours till you “arrive,” you’re on the lookout for cool sights and stops.

Just make sure to bring your phone and a car charger, so you can …

  • Use the Progressive Insider’s Guide and apps like Roadside America and Along the Way (for sights and stops), Sit or Squat (clean bathrooms), and Hotel Tonight (last-minute lodging).
  • Use reviews to choose where you stay, once you narrow your options based on must-haves (like a pool and free breakfast). Just make sure the reviews are recent; hotels change management.

… but have some old-fashioned resources on hand, too.

  • Buy a paper map to use if you lose reception. And, consider pulling it out before you leave, circling your starting point and final destination, and then mapping out a scenic route by hand.
  • Pick up coupon books from rest areas and grocery stores. Sometimes, you’ll find better deals for local attractions there than online.

Tip: Considering options besides hotels (like camping and tenting) gives you even more flexibility for last-minute accommodations.

PLAN: “Absolute musts.” WING: Every third day.

At the center of your itinerary, put the things you have your heart set on doing. Try to limit yourself to one a day; then, plan around them.

To choose your “must-dos”:

  • Include visitor centers, which are typically around state and city borders, in your route.
  • Talk to people—locals, especially. Ask about hot spots for entertainment, lodging and food—and give them a little idea of what you’re looking for. You might even ask for suggestions on when to go and any other insider information.
  • Visit Progressive Insider—it’s a place where people who travel post their favorite sights and stops. Follow the route you’re taking on the map and see what’s along the way.

AND … although this seemingly goes against everything we just talked about … it is equally important: Give yourself what travel writer Rick Steves often calls a “vacation from your vacation.”

That means, about every third day of your trip, plan nothing. Sit outside sipping coffee and listening to nature. Watch one sunrise and one sunset. Get a little bit lost. You’ll feel recharged.

Tip: If there’s a mix of vacation styles in your family or group, make a pact. Agree to always invite the others to join you for whatever you want to do. But, there’s no obligation to do so. (Doing this upfront will save conflict and hurt feelings later.)

PLAN: What you want to spend. WING: Your expectations.

It’s easier—and much more flexible—if you focus on how much you have to spend overall vs. trying to stick to a daily amount. (Unless you’re Rachael Ray, on a $40 budget.)

So, figure out what you can spend, and work backward from it. If you go all out on dinner one night, you can go frugal the next two to compensate.

Resist the assumption that you have to dine out for every meal, too—this is an easy way to cut costs. Stop at grocery stores (many offer hot food to go—perfect for a picnic), and take advantage where you can of free continental breakfasts and lodging that offers a microwave and refrigerator.

Sign up for hotel perks, too. You get credit for each stay—so who knows? Maybe by the end of your trip, you’ll have a free night.

And, keep in mind—it’s sometimes the most mundane parts of travel that end up being the most memorable.

On a recent trip to Boston with my fiancé, for example, one of our favorite memories was the night we just roamed around Boston University and ended up in the stands at a women’s rugby game, eating cannoli we’d bought after dinner.

And another co-worker said he remembers being 8 or 9 and camping in Las Vegas. After trying to sleep in 100-plus-degree heat, his family drove to a mountain range in California and had a snowball fight.

Basing your expectations on what you get from the trip—and making that the most important thing—frees you from feeling disappointed if things don’t work out like you planned or you don’t get to do everything you wanted.

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