How to plan for a LONG TERM trip!

So you are doing the thing? You are quitting the job? Taking the gap year? Spending the savings? You’re finally ready to take the long term trip of your dreams?

Potentially you have had this plan in place for years, you saved the money and you are ready to go for it. Or you are like me, you have been saving the money and doing the real world career thing and realized – you have the money and the dreams and the time! You are in a transition and you realized there is no better time than the present!


How to Actually Plan for a Long Term Trip

Now — how do we even start planning something like this? 

Check Your Mindset

Step One: Do not get overwhelmed – people do this all the time. Everything will work out and be great! I took a 6 month trip to Southeast Asia in 2023, so I am here to tell you, you can do it! It is not easy, but boy oh boy is it worth it.

Set Your Boundaries

Step Two: Set your boundaries!! This is important!

  • How much money are you comfortable spending?
  • How long are you comfortable being away from home?
  • Are you okay to miss the Holidays with your family? When is the best time of year for you to travel?
  • What are your standards for lodging? Do you need a hotel, a hostel is fine, a tent?
  • Do you like to rent a van or can you kick it on public buses?
  • Do you always need to know where you are staying, or can you roll up to a hotel mid afternoon and book?
  • Do you have a buddy or are you solo? If you have a buddy, make sure to align on these questions ahead of time.

Look at Where You are Now

Step Three: Evaluate your current situation

  1. Are you renting a place? Can you save money by moving out and potentially putting your stuff in storage or saving it at a friends? If you own a home – can you rent it out?
    1. This may not make sense if your trip is less than 3 months, but once you get into the 6 month or year travelling – those $ you are saving can make a huge difference for your trip and your return. 
  2. Set a budget
    1. Do you want to stay for a certain length of time 
    2. Do you want to stay for a certain amount of dollars 
    3. What are your monthly bills that will continue while you are out
      1. Car Payment 
      2. House Payment 
      3. Loans 
      4. Health Insurance
  3. Get rid of miscellaneous expenses
    1. Subscriptions 
    2. Car insurance 
  4. Think of stuff that you are paying monthly – the best way to avoid accidental spending is to look into your spending history and see what you are spending each month
    1. I have a one-deposit checking account, if I don’t make one deposit per month I get charged a fee. Normally part of my pay check funnels 

Make a Big Picture Dream Trip

Step Four: Create an Itinerary

  • Folks that know me are currently shaking their heads that I said this… but it is true!! I always have a loose itinerary. Perhaps I don’t know every city that I will visit, but I know the dates that I am flying in and out of Mexico. I know the second Tuesday that I want to be in Tulum for Salsa dancing night. I know that I want to be in a certain city during a Holiday/Festival!
  • Make your itinerary to fill in what you need to fill in to feel good about it!
  • If you are like me, potentially you are just writing your flight details, and marking what dates you have to be out of what country to not overstay your visa – that is fair! Be warned that the less planning you do ahead, the more you will do while on the trip. I personally like to plan 2 weeks at a time, so every two weeks I bunker up at a nice coffee shop in the morning and don’t leave until my following two weeks of accommodations and transportation have been booked or thoroughly researched.

Research Travel Insurance!!!


  • Travel insurance gets it’s own step due to its IMPORTANCE. You will only make the mistake of not getting travel insurance one time!!
  • My best advice, do your own research and ask fellow travelers how their experiences were.
  • Evaluate what you need with travel insurance
    • Does your credit card cover certain things? If it is a travel card then most likely yes (If you do not have a travel card, then get one!!)
    • Do you have primary healthcare? If so, does it cover out of country expenses?
      • I did not for my last 6 month journey, so I went with IMGlobal Platinum plan! They covered 100% of doctor visits/prescriptions.
    • How is the healthcare/safety where you are visiting?

I hope you have an amazing long term trip!

Do you have any other tips for planning for a long term trip? Comment below.

Be sure to check out my Instagram account for more photos!

Be sure to check out a few of my recent travels:

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