Poker Road Trip

25 Things You Must Do When Planning A Long Road Trip

Even a short road trip requires a certain amount of planning. At minimum, you need to figure out where you are going and how you will get there. You need to  know what to pack and how to finance the trip. Even if you tend to play vacations by ear, you at least need to decide when you are leaving.

Long road trips, such as the year long travel of our Poker Pilgrimage, require even more substantial travel planning. Travel lasting more than a couple of weeks requires addressing myriad issues. What will you do with your mail? How will you pay your bills? What sorts of insurance do you need? While not yet having all of the answers, we are currently working to generate the right questions.

Early Stage Road Trip Planning 


Every journey first requires a travel plan. When will you leave? Where will you go? How long will you be gone? Planning for a year on the road, for example,  is a vastly different task than taking a long weekend. Deciding on your basic journey specifications allows you to consider what else you need to know.

In our case, we are planning for a year-long trip. We know we will be travelling throughout the US,  visiting some of our favorite US cities (and others we have not seen), and playing in as many large poker rooms as we can. We also must solve several problems related to being digital nomads for the year.


Once you know where you want to go and for how long, you need a road trip budget. Are you planning luxury travel? Will you be back-packing across Europe? Are there ways you can make money on your journey?

We have roughed out an initial budget for our trip, but still have a lot of numbers work ahead of us. Fortunately, we have a main hustle, a side hustle, and a number of micro-hustles which are all portable. We’re definitely planning to supplement our savings with income we make on the road.

If you’re looking for more about budgeting for long-term travel, Ryan from Desk to Dirtbag offers a wonderful resource on how to make long-term travel possible.

Things You Must Do Planning For a Road Trip


Where will you stay? This is, of course, the natural next question. There are a wide variety of options to explore:

  • Camping or truck camping
  • Hostels
  • House-sitting. There are a number of websites which will help you to find free, or even paid, accommodations. Stays range from a few days to weeks. Responsibilities vary a great deal, typically including tasks such as watering plants and taking care of pets. Check out Trusted House-sitting for some tips on getting started.
  • RV  travel
  • Rentals through sites like AirBnB, HomeAway,  VRBO, or Real Estate rental offices
  • And of course hotels. You’ll definitely want to explore the wide variety of hotel booking websites to make this option more cost-effective.

For now, we are thinking we will use a combination of rentals and hotels, with hopefully some house-sitting mixed in. We’re not campers and feel a bit old for hostels. And we have pretty much ruled RV travel out as a viable option.

There are a number of key logistics that you will need to figure out when planning long-term travel.

  • Where will you get your mail? What will you use as your “permanent” address?
  • How will you maintain residency in your home state while you are gone (for voting, potentially insurance, and other purposes)?
  • What will you do for health insurance, if you are currently covered by an employer or a state-run plan?
  • Does your car insurance cover the trip you are planning to take?
  • Do you need travel insurance?
  • How will you ensure regular access to wi-fi?
  • How will you make sure you get all of your bills?
  • And your paycheck if you are continuing to work remotely?
  • How will you keep an adequate supply of any prescriptions you might need?
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What to Do with Your Stuff

You may, like us, decide that your road trip is a great opportunity to go rent and mortgage free. We will be selling our house and waiting to purchase or rent a new home until we return. If this is your situation, what will you do with your stuff?  We see four potential actions here:

  • Determine what is going with you.  Make a road trip list to know exactly what’s going mobile with you.
  • Sell your stuff!  Considering selling furniture, excess clothes, etc. on Craigslist, Ebay, or other websites.
  • Give things to friends and family.  Offload stuff to your kids, family, or friends who might appreciate them.  Entrust things you want back in the future (e,g, photo albums, art) to family members or friends for safe-keeping.
  • Donate. Donate items to organizations such as Goodwill or Big Brother, Big Sister.
  • Storage. This really should be the last ditch option. Every month that you pay for storage cuts into your trip budget. And the bigger unit you rent, the bigger the bite. Your long-term road trip offers a perfect opportunity to adopt a minimalist mindset.

We’ll likely do a little of each of the above with storage kept to a minimum. But a few heirlooms and furniture pieces will likely have to be stored. The culling process has already begun. Just last week, I gathered a variety of books, CDs, and DVDs and sent them to Decluttr. I eagerly await the cash in exchange for this box of items we no longer need.

Final Road Trip Preparation

Your trip is finally drawing near. You have made all of your plans and gotten rid of your possessions. Believe it or not, there are still a few things that need to happen before you go.

  • Auto maintenance. Unless you are using public transportation, make sure your car, truck, or RV is in tip top shape. You don’t want to get 500 miles into your trip and have your car break down.
  • Annual physical. Like your car, you need to check that your body is in good shape. Make sure you are physically ready for the road trip and that your prescriptions are updated. And yes, this includes any mammograms, colonoscopies, and blood work that you may have been avoiding.
  • Coordinate with family. Make sure your family always knows how to reach you. Designate times to check in with them so they know you are safe. Many long-term travelers find blogging about their trip enhances their enjoyment of their travels.  This allows them to share their experiences with friends and family as well.
  • Make copies of and store originals of important documents. Get a safety deposit box at a local bank for all of your important documents. You will want to store originals of your birth certificate, social security card, car title etc. Also, copies of your bank account, credit card numbers, license and passport. There are all sorts of mishaps that might befall you on the road. Your most important information needs to be safe and sound while you’re away.
  • Cancel all services you won’t be using on the road . Turn off your utilities, cancel your cable, and turn off that subscription to the wine of the month club. Don’t forget to return your library books!

You’re Almost There!

Once you have taken all of the steps above, you are ready to go. Almost.

The week before departure, empty your fridge and pantry while stocking up on any foodstuffs for the road. Also take a dry run of packing the car, truck, or RV to make sure that everything you plan to take with you will actually fit. Then have that bon voyage party with your family and friends. And rest easy knowing that you have set yourself up for a fabulous long-term road trip.


This page will be updated as we explore each of these areas further in planning our own road trip. In order to receive updates by email, be sure to go to the sidebar and subscribe.

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