How to Rock Out Your Own Extended Road Trip: Part I {The Planning}

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In 2015 I stopped working, put my ish in storage, and wandered around the U.S. and Canada for 3 months with my dog, Tango. It was one of the best things I’ve ever done in my life. You can do it too (or something similar). Here’s the first in a 5 part series on how to rock out your own extended road trip! If you start planning now, you could be ready to go in just a couple months…

Step 1: Ask yourself the following questions and literally write down your answers. 

* WHY are you going?

Do you want to see the world? Do want to get away from a stressful job or relationship? Are you hoping to find some inspiration? Hoping to find yourself? Doing it just to say that you did? Whatever the reason, it doesn’t matter to me and shouldn’t to anybody else. What does matter though are your answers, because they will affect how you go about planning your trip. Be honest with yourself here. It will make the planning process, as well as the trip itself, more enjoyable.

>>>  Really think about it. If you’re depressed, being alone all the time could make you feel worse, rather than better. Maybe get a friend to go with you. If you want to see the world (i.e. multiple countries), your plans might need a different (longer) timeline and (bigger) budget. If you’re stressed, spending as much time outside as possible will do you wonders, but it’ll also require more preparation.

* How long do you want to go?

Do you just need a couple weeks off? How about a month? Three months? A year? I know several people (myself included) that started planning their trips on a small scale and then once they left, realized they needed more time. Answering this question will determine the preparations you need to make. I recommend over-estimating how much time you need, just to be on the safe side. You can always end your trip early if you feel fulfilled.

>>> When I started planning my two week road trip from Kentucky to California, it turned into a 3 month endeavor between the U.S. and Canada.

* WHO will go with you? 

Do you want this experience to be a personal one or are you wanting your friends or family to share it with? I would have loved taking another person with me, but nobody else could take off that much time, so it ended up being just me and Tango, which worked out wonderfully. Tango did not split any costs with me though, which affects the next question:

* How much money do you currently have? How much will you NEED?

Some people are frugal by nature, have a lot saved, and could literally pick up and leave whenever they want. Most others though will need time to save up. Do you want to camp to make things cheap, so you can stay out longer, or will you want to stay in hotels along the way? Will you be eating real food or going to Taco Bell every day? Will you be traveling solo or will you have a friend or two to split costs? If you’re eating Taco Bell every day, you might be better off alone in the car. ; )

>>> Traveling alone and camping most of the time, I budgeted $1, 500 per month. I could have done it for cheaper though, and will be planning on $1,000 or less, per month, for my next trip. I don’t want to dip into my savings, so I’ll be saving the cash up prior to leaving. We’ll go more in depth into the money aspect in the next post…

* WHERE do you want to go?

Do you just want to cruise around your state, your side of the country, or to another country completely? I had my dog with me, so we were confined to drive-able places. You certainly could follow this U.S. road trip plan to see as much of the U.S. as you can. I’ll warn you though: you may feel stressed trying to accomplish so much. During my first trip, I went to a lot of places, but I didn’t spend as much time exploring each one thoroughly. I was so preoccupied with getting to the next place I wasn’t fully present where I was currently. I still had fun, but the next trip I’m planning on remedying that with more quality time in fewer places.

>>> We stayed in thirteen states and two provinces during our trip, most of them in the west. When it was all over I realized how much more I wanted to see, so the next trip will include a lot of the southern states and eastern seaboard. Which brings me to my next question:

*WHEN do you want to go?

Depending on your schedule, you have to decide what time of year is best for your trip. Additionally, you have to think about what the weather will be where you are when you go. Every region of the world has it’s peak season so you have to take that into consideration as well. Getting a reservation in a national park during the summer is something you’ll want to book weeks or months in advance (check out the app). If you’re ok winging it though, then that’s a different story.

>>> My last trip began in mid-April and went throughl the end of July. During the first 6 weeks, the spring weather (read: cold and rain) put a literal damper on some of my outdoor plans in Colorado and Wyoming. I’d been camping then, and will be again, so I would change my timeline for different parts of the country in the future. Seeing the south in the winter and spring, the west coast and north during the summer, and the north east in the fall sounds like a better idea.

Good luck answering those questions!

> > > If you’re traveling with somebody, I’d suggest answering them individually first, then sitting down to discuss, alter, and create your shared ultimate road trip vision.

Stay tuned for Part II: The Preparation!

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