Road Tripper Planning Guide

If you’re like me, you don’t like to waste time on a trip looking for a food, safe places answer the call of nature, or figuring out if you’re going to score a comfy bed for the night on the fly.

Choose your road trip route

Choose the locations you want to explore – Road trips can be as long or as short a your wardrobe and your relationships will bear. Be realistic as to how many nights you want to stay in a particular location and plan out the key attractions you are planning to check out to give yourself an idea of how long you will stay in a particular area.

Pitstops are important – Get a general sense on where you might want to pit stop to stretch you legs and let your passengers answer their nature calls.

Plan time to explore – If you have the time, plan time to just explore and see what the areas has to offer.

Plan your meals

Make reservations – Make reservations at restaurants you plan to eat at whenever you can. It’s a bummer to arrive somewhere tired and hungry, and facing a 45 minute wait to get seated.

Compare prices early & save money

Accommodations comparisons – I compare accommodations costs with aggregator sites such as and 6-8 weeks before a trip to get an idea of costs. Keep in mind that weekends, holidays, and popular seasons typically command higher prices, so research costs for the dates you actually have in mind for travel. If my options are flexible, I tend to favor the hotels that have a flexible cancellation policy. Don’t forget to figure in the cost of parking if you are exploring a high-density metropolitan area.

Car rental comparisons – You can compare car rental costs with aggregator sites such as and – I check out both a few weeks before a trip to get an idea of costs. A one-way trip will incur a significant drop fee, so roundtrip is the way to go if you don’t mind the drive, haven’t gotten sick of your road trip buddies, and have the time off from work. For 3 or more people, I try to get a bigger car than I need so people can spread out and you aren’t cramped for space on a long drive.

Flight comparisons – I use Hopper Reports  to check out prices for a flight and the best time to buy.

Use points for credit card airline miles – I try to use miles where I can. The one-way ticket that was the equivalent of $65 cost me 3,000 points. Keep in mind if you will be charged for checked luggage! In addition, if your airline does boarding groups, don’t forget to check in as soon as check in becomes available so that you get into a decent boarding group. There are reminder apps out there that will remind you to check in, but seriously, just use your calendar or alarm reminder on your smartphone…you don’t need an app for EVERYTHING.

Cash back shopping – Before I buy ANYTHING online (Home Depot,,,, etc.) I check to see if a retailer is listed with Mr. Rebates to see if I can earn a percentage back from what I spend. By going through the Mr. Rebates site, I typically earn 2% to 20% cash back on my online purchases from participating retailers. Click on my Cash Back Shopping  referral button below to earn cash back.

Mr. Rebates

Check car insurance

Check if you are already covered – Don’t forget that if you have comprehensive car insurance, your policy will frequently extend to rental car coverage. Your credit card will frequently cover rental car insurance as well.

Independent car rental insurance – I ALWAYS purchase insurance when renting cars for road trips. You can purchase standalone car rental insurance (Collision Damage Waiver – CDW and Loss Damage Waiver – LDW) for a fraction of the cost before your rental date from an independent insurance service group if you hate having to pay $10 – $30 a day.

Safety & road trip etiquette

Be Well Rested – Get rest the night before you drive. It’s simply not safe to drive tired.

Be Well Fed & Stay Hydrated – Pack snacks, plan key meals, and stay hydrated when driving long distances. It’s tempting to skip the water because you want to cut down on the driving time, but a 15 minute bathroom and break stop every couple hours will keep you a safer and more alert driver.  Staying hydrated will keep you from getting “travel constipation” and dehydration headaches.

Road Trip Etiquette – You’re crammed into close quarters with your friends. family, or complete strangers. Here are some tips on keeping the peace and a drama-free trip.


Music & Games – Road trips are fun when you can listen to music that everyone enjoys, or play games . Who controls the music? The driver, of course. Here is a list of games from Edmunds. We also like to play heads-up charades with our smartphones. Bring earplugs, headphones, or noise-cancelling headsets if you are planning to sleep during the drive.

Travel tools

Gas Buddy Trip Cost Calculator – Estimate your gas cost by entering your starting and ending location and the make, model, and year of the car you are driving. I usually over-estimate costs for road trips by x2 to account for all the pit stops, exploring, and extra weight from people carrying and luggage.

Manage trip documents with AdventureAlly – I use the free AdventureAlly travel document vault to store images of my travel documents such as my passport, travel insurance, and offline copies of my itinerary in the event that my wallet or luggage gets stolen.  This site can also generate a travel map for those who wish to generate a map of the countries they have visited.

Map Your Route – You can use Google Maps to create a shareable map of your travel route, identify pit stops, activities, and dining locations. See the Spook Quest Haunted Road Trip example.