How to Plan a Successful Road Trip

Greetings, Travelers!

Whether you are a regular road warrior or planning your first trip, I have created this blog to help you make the most of your time in a new city. However, before I bombard you with sample itineraries, challenges, and tips, I felt it was important to build a strong foundation. My best friend and road trip co-captain, Josie Berridge, will be chiming in on this entry, and together we will share our time-tested tactics and resources. Below are 10 suggestions to ensure you have a successful road trip:


1)    Request gas money in cash from all your travelers.

We list this first because it is our biggest and most important suggestion. Money can get very sticky while traveling, and the last thing anyone wants is to be chasing their friends down weeks later for cash. Instead, pre-calculate your gas expenses by dividing your estimated travel mileage by your vehicle’s average highway MPG, then multiplying that number by the current average cost of fuel. If you are worried about your math or unsure about your vehicle’s fuel economy, this website is a very helpful resource. Divide the estimated total by the number of travelers and have everyone bring that amount of cash with them on the trip. Pool your cash together, place it in an envelope, and keep it in a safe place. Use that cash for all of your fill-ups, and record your stops and expenses on the envelope (not that you don’t trust your friends, but it is a smart idea to make sure none of the money is unaccounted for). As a courtesy to the vehicle owner, we recommend topping off the car when you arrive back home and splitting any remaining cash amongst everyone. Do it. You won’t regret it!

2)    Choose your road trip buddies wisely.

We say this tongue-in-cheek with an ounce of truth: not all road trip buddies are created equal. Do you like to blast your 100-song Disney playlist or do you prefer the tranquil silence of the road? Do you like taking regular pitstops or driving as far as you possibly can without peeing your pants? These are important questions to ask when considering any road trip. If you find partners with your similar preferences, your time on the road can be almost as much fun as exploring at your final destination. If not, you may regret taking the trip in the first place.

3)    The front seat passenger cannot sleep. Period.

This detail is often overlooked, but it is crucial to a successful journey.  Frankly, asking any driver to captain the ship while all of the passengers take naps is both unfair and unsafe. Keeping the current driver awake and alert is the co-captain’s job, which leads us to our next suggestion…

4)     Think about entertainment in advance.

It is easy to forget about entertainment, but doing so can help keep your trip safe and fun. Radio stations cannot be counted on to provide entertainment, especially if you are traveling through mountains or remote areas. We suggest creating your own playlists and stopping by the local library for a few books on tape. If any of your co-captains can read out loud to the driver, even better! (Personal Experience: The two of us have spent a lot of time on the road laughing at each other’s voices as we read YA novels out loud to each other. It sounds weird, but it’s not. It’s awesome.)

5)    Minimize lodging expenses as much as you can.

Money is precious, and we believe that money spent on hotel rooms (especially when you are a 20-something traveling without family) is a huge waste. Question: Would you rather spend $200+/night on a room that you will barely spend time in or save those funds for additional attractions, dining, etc.? No brainer. When planning any road trip, we suggest thinking about destinations where you may already have connections, even if they are a long-lost relative or an old acquaintance from high school. We are willing to bet that they wouldn’t mind a few couch surfers if it means you will buy them dinner or give them an excuse to be a tourist in their own city. The savings is well worth it! If you must invest in lodging, we suggest resources such as Airbnb or, which help connect you with those who are putting their apartments, spare bedrooms, or couches up for nightly rent. This is a great way to stay in the heart of a city (while potentially making new friends) without the big hotel expense!

6)    Minimize food on the road.

Now, we love Taco Bell as much as the next people, but repeated stops for fast food on a road trip are a serious money suck. Our suggestion is to borrow or invest in a small cooler, in order to pre-pack healthy items you may already have at home like sandwiches, bread, PB & J, string cheese, and even a six-pack of coffee drinks that you would pay 3x as much for at a gas station. That way, you can all stay awake and energized without the extra cost or pitstops.

7)    When you do not have a reliable vehicle, renting a car is a worthwhile investment.

By now, you realize that we are money-conscious people, so we do not make this suggestion lightly. If you have a reliable vehicle that is not going to need an oil change before you come back from your trip, by all means go for it. That has not always been the case for us, but we have each had at least one successful road trip with a rental car and are here to provide tips to make the most out of your investment.

Cons: At least a $25/day additional expense, and potentially limits the amount of drivers you have, depending upon insurance stipulations (which we will discuss in a moment).

Pros: You have a reliable vehicle that gets great gas mileage and most likely roadside assistance is included.

Our Advice:
1) Skip the luxury. Select an economy car that gets great gas mileage, which will hopefully help you make up for some of the added expense!

2) Check your insurance before you purchase it from the rental company! If any of you have a MasterCard, a very well-kept benefit is that they often come with Car Rental Collision Damage Waiver Insurance if you charge a rental on the card, which typically covers personal liability, collision, and theft. Check this website and call the number on the back of your card to make sure. Also, if you already have your own auto insurance, contact your insurance company to see if your policy extends to rental vehicles. Having either can end up saving you a lot of money! Do your best to have as many insured, SAFE drivers as you can.

8)    Create at least a basic itinerary.

Most road trippers we know want to be wild, spontaneous, fly-by-the-seat-of-their-pants kind of people, but this can cause huge headaches for the loved ones you are leaving behind. Do yourselves a favor and create a Google doc that you all can share with your friends and family. On this document, list all of the major destinations you plan to hit and your approximate ETA at each, as well as emergency phone numbers. Now, this doesn’t mean that you can’t make a random, unplanned pitstop at the World’s Largest Frying Pan. On the contrary, we highly encourage these kinds of ridiculous adventures. However, if you decide to go to Boston instead of New York City, update your Google doc if you can so that you won’t leave anyone at home in a panic. You’ll be thankful you did.

9)    Print out directions in advance.

I have personally had to learn this lesson the hard way and I will never leave home without printed directions again. I know what you’re thinking, “I have a GPS, I can skip this one.” My friend, your GPS is not fool-proof. All it takes is lost signal at a key moment or the GPS deciding to take you downtown vs. your actual destination because it simply doesn’t know where your destination is. We’ve all been there. Don’t be those lost, helpless people that need to stop at McDonald’s to use the free WiFi. Go to Google maps, enter your destinations as specifically as you can (we recommend at least having your lodging addresses handy), and print. Best case scenario, you won’t need them. Worst case scenario, see above.

10) Fill your trip with as many adventures as you can. You can sleep when you get home.

Here is where I come in! I am here to help you make the most of your time in any city I have previously traveled to by providing sample itineraries and lots of recommendations for dining and attractions. If I have not yet blogged about the city you are visiting, Yelp is an excellent resource to find local favorites that are worth your time and money. TripAdvisor can also be a great resource, but WARNING: the items at the top of any city’s list tend to be the more expensive, 5-star options that aren’t truly the best choice, especially if you are on a tight budget. I recommend double checking between the two if you are torn between a few options. Either way, don’t waste your time in bed. Wake up early and seize the day!

That’s all for now! Safe travels, friends!

Adventure is Out There

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