Planning for that perfect road trip could get overwhelming and daunting. Sharing my tried-and-tested 3-step recipe to help you optimize your road trip planning and enhance over enjoyment.

Step 1 – Choose the right destination

Enroute to Hot Springs Mountain Tower, AR

This seemingly trivial step could be the most time consuming. First, find your travel goals and driving capacity. Then narrow down your research by season or driving capacity or activity. Below would give you a perfect head-start for any road trips from Chicago.

Seasonal Chicago Trips: Spring, Summer, Fall , Thanksgiving, Winter.
Time-based trip ideas: Weekend Chicago Getaways, Long Trips From Chicago
Activity-based suggestions: Camping, National Parks, RV Trips
Finally, our iconic Friends-only No-Regrets Nature and Adventure Road Trips.

Step 2 – Find the right accommodation

View from the backyard of the cottage I stayed at Hot Springs, AR

I go for cottages from Airbnb or Vrbo, period. If you value experiences more than the opulence of a x-star hotel, look no further than the vacation homes. I would stay at a hotel only if I am traveling just with my family or making last-minute reservations.

Tip: Pay a little extra and be biased towards locations with liberal cancelation policies during the bookings, travel cancellations are more common than we think!

Our “backyard” at Smokey Mountains National Park

I almost always plan a road-trip with multiple other families so here’s my cheatsheet when it comes to technology-

•  I use shared Google Docs to collaborate with other trip members to split the work and efficiently share the progress with all.

•  I use Google Maps Timeline feature to automatically log my travel times, places I visited and the like. 

•  Check TollGuru and make sure you have the right car tag (I-Pass/EZ Pass etc.) to breeze through the tollways without worrying about the fines.

•  If you are going in multiple cars, enable Location sharing between friends, to efficiently share your road trip progress. I use Google Maps for the same and find it the most reliable.

•  If you are doing trails/hikes, I would highly recommend AllTrails. Losing your way during a trail could be very harrowing/frustrating experience. I have been using AllTrails Pro (which gives you ability to download offline maps) for many years now and would call it an indispensable tool. It helped me immensely in places such as the Endless Wall trail in WV, Cherokee Falls trail in TN, Lover’s Leap trail in AR, Wanatee Park trail in IA, Trail of the old Oaks in IL when I was looking for directions and there was no one to ask.

Step 3 – Be prepared for travel emergencies

You can have a head-start via this emergency checklist and then add your own tweaks to get ready for the curveballs.

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That’s it! Happy Road-tripping!

Taken at Shenandoah National Park