BootsnAll indie travel guide

Master Checklist for Planning Your Trip


checklistimageSome of us are list people. Whether it’s planning a RTW trip or simply a trip to the grocery store, we don’t leave home without a list. When planning a trip of this magnitude, we like to have all our ducks in a row, which is why we created this master checklist to help you stay organized in your RTW planning.

The timeline we suggest is exactly that – a suggestion. Some people take years to plan their trips. Some do it in a month. For those who signed up for Plan Your RTW Trip in 30 Days, this checklist coincides with the emails, articles, and action steps for each day.

For those who signed up for the Family Edition of Plan Your RTW Trip in 30 Days, you want to download this checklist, which is customized for families

For those signed up for the Career Break Edition, this checklist is customized for you.

You can print the page and/or download the PDF, and start crossing stuff off as you go, or just bookmark it (hit CTRL-D) and come back as often as you need.

Master RTW Planning Checklist

1 year + away prior to estimated departure

  • Decide why you are taking this trip. Coming up with your why will help shape your trip.
  • Choose the pillars, or must-sees for your trip. These will help shape your itinerary.
  • Come up with a preliminary budget
    • Research your pillar countries and per day costs of traveling there
    • If you signed up for Plan Your RTW Trip in 30 Days, download the RTW Planning Spreadsheet (introduced on day 4) and enter countries you plan to visit and per day costs in tab 1 (if you are not taking part in RTW 30, start your own spreadsheet to stay organized)
    • Go to Indie, enter your estimated route and dates to get a price on your flights
    • Total your flights and costs per country to find out your preliminary budget
  • Figure out how much you can save per month
    • Enter income, and monthly bills into the RTW Planning Spreadsheet to see how much saving potential you have per month
    • Put a plan together to cut unnecessary spending
  • Find ways to make more money
    • Evaluate all your possessions
      • Make a list of what you will keep
      • Make a list of what you can get rid of (add these to the RTW Planning Spreadsheet)
      • Make a list of what you can sell for money
      • Make a list of what you can give away
    • Start selling some of your unnecessary possessions to add to your travel fund
    • Devise a plan for storing the things you will keep for after your trip

6 months – 1 year prior to estimated departure

  • Find your departure date
    • Evaluate your current bank balances
    • Look at recurring monthly bills you’ll have to pay while on the road
    • Come up with an amount you want to have for your “coming home” fund
    • Add all these figures into your RTW Planning Spreadsheet to figure out how soon you can leave
      • Figure out the total amount you need to save, divide that by your monthly savings potential, and you have how many months until your departure date
    • Set your departure date
  • Getting rid of housing
    • If you rent, look at your rental agreement and give the appropriate notice that you are moving out
    • If you own, decide on renting vs. selling
      • If selling, talk to a real estate agent and get a plan in place for when you will put your house on the market
      • If renting to someone else, look into all options
      • Ask family, friends, and friends of friends if they may be interested in renting
      • If you don’t know anyone interested, have a timeline in place to take out ads in the local newspaper and on sites like Craigslist and Airbnb.
      • If renting, find a family member or close friend in your hometown to be your go-to person for any issues that may arise
  • Start the immunization process
    • Research which shots are required for the countries you will visit
    • Research which shots are recommended for the countries you will visit
    • Research costs of these shots where you live
    • Make a decision on which ones you will get
    • Schedule your first round of shots (remember that some shots are done in a series, with the first shot 6 months before the second)
  • Decide what to do about your job/career
    • If you want to return to your current job, look into sabbatical policies
    • Talk with your boss/HR about the possibility of a sabbatical or leave of absence
    • If you don’t want to return to your job, start planning now for what you will do after your return
  • Passport: If you don’t have one, order it. If you do, make sure it’s valid for the length of your trip and has enough pages for stamps for each country you will visit

3 – 6 months prior to departure

  • Consider slow travel as part of your itinerary
    • Look into spending more than a few weeks in one location
    • Choose a few locations where you may want to do this
    • Research long-term rental costs and options
    • If you want to travel slowly, build into your itinerary and adjust your budget accordingly
  • Decide on flights – Traditional RTW ticket vs. buy as you go vs. combination
    • Look at your itinerary and research all possible flight options for your trip
    • Get prices for each option
    • Prioritize price vs. freedom vs. having a plan
    • Decide which option you will go with
  • Solidify your route
    • Decide where else you want to go and start building your route around your pillars
    • Research seasons – high and low and weather – in each place on your itinerary
    • Start planning the order of places you will visit and look into flight options/costs, no matter what your preferred flight plan
    • Decide where you will begin your trip
    • Book your first flight, first few legs, or entire trip with the provider that’s best for you

2 – 3 months from departure

  • Start telling people
    • Come up with a plan for telling family and friends about your trip
    • Come up with a plan for breaking the news at work, even if you won’t tell them until right before you leave
    • Start spilling the beans
  • Look into your accommodation options
    • Research all options available – hotels, hostels, rentals, house-sitting, camping, couchsurfing, etc.
    • Research prices for all options that interest you
    • If planning your trip in advance or traveling during high/festival/holiday season, send inquiries and make reservations when necessary
    • Adjust your budget accordingly
  • Research overland travel
    • Research different regions you plan to visit and what overland travel is like there
    • Look into traveling overnight in the regions you will be visiting
    • If you are traveling in more developed and expensive regions, research overland travel there
    • Research flights in those more expensive regions-they may be cheaper
    • If passes are available, cheaper than flying, and must be purchased before departing, buy them
  • Decide on travel insurance
    • Research the difference between trip protection and travel insurance
    • Shop around to see what each company offers (don’t forget to read the fine print!)
    • Have a plan in place for being covered medically when you return
    • If you plan on taking part in any extreme activities, know what each policy does and doesn’t cover
    • Make a decision and buy the policy best for you

1 – 2 months prior to departure

  • Get your gear and clothes packing list in order
    • Decide which type of camera to bring
    • Decide whether or not you will bring a laptop and/or tablet
    • Decide whether or not you will bring an ereader
    • Decide whether or not you will bring a phone
    • Get a preliminary packing list of clothes together
      • Start a list of what you have and what you still need
      • Start shopping and keeping an eye out for what you still need
  • Choose your luggage
    • Decide which type of luggage you will bring (backpack, suitcase, or hybrid)
    • Decide which type of daybags you will bring
    • If you need to purchase anything new, go to a store and look at your options
    • Test out any new bags before purchasing
  • Packing list
    • Come up with a master packing list, broken down into categories – clothes, gadgets, toiletries, and first aid
    • Get everything together that you wish to bring and lay it all out somewhere
    • Do a test run and pack everything you want to bring
    • Adjust and prioritize if you have too much stuff
  • Get rid of your house/apartment/condo
    • If your rental agreement ends or you sell your house and will need a place to stay prior to leaving, set that up now
    • If you own, are renting your place out, and DON’T have someone you know to rent, take out ads in the local newspaper, and on sites like Craigslist and Airbnb
    • Downsize as much as you can and get rid of anything else you don’t want to keep around.
  • Get your visas situated (or have a plan in place)
    • Look into visa requirements for the countries you are visiting
    • Get any visas in advance that you can
    • If you will be obtaining many visas on the road, research what you will need to do so
      • Make and bring copies of your passport, passport sized photos, and make sure your bank account/credit card information is easily accessible from the road
      • Have a plan in place for what to do about proof of onward travel

1 month prior to departure

  • Automate your bills/Banking
    • Sign up for an online money management software (we like Mint)
    • Know what bills you will continue paying while on the road
    • Get them all set up to be paid automatically
    • Consolidate and delay – IRAs, investments, automatic transfers, etc.
    • Cancel services and bills that you will no longer need (Netflix, cable, etc.)
    • Implement a plan for paying or deferring student loans
    • Look into your bank’s ATM fees – get their policies in writing for withdrawing money internationally
    • Shop around for a different bank and find one with the least amount of international fees
    • Look into your credit card fees – get their policies in writing for use overseas
    • Look into and sign up for a travel credit card
    • Designate a power of attorney at home
    • Taxes: Will you need to file your annual return from the road at some point during your trip? Have all documents you will need scanned and easily accessible
  • Working on the Road
    • Decide if you will need to work on the road in order to travel for as long as you want
    • Look into your working on the road options
    • Get any necessary paperwork together – diplomas, certifications, resumes, letters of recommendation, etc.
  • Staying connected
    • Make sure anyone who you hope to stay connected with is signed up and knows how to use Skype, Google Hangouts, FaceTime, etc. Do a test run before you leave
    • If you plan on having a blog, start it before you leave
    • If you hope to monetize your blog, start it well before you leave and learn as much as you can about making money from your blog
    • If you are counting on funds from your blog to supplement your travels, have a plan to start making money long before you leave
  • Book 1-3 nights in your first destination
  • Make any last minute doctor or dentist visits

2 weeks prior to departure

  • Quit/leave your job
  • Pack all the things you aren’t bringing and get them in storage
  • Have a going away party
  • Eat and drink at all the places you will miss

1 – 7 days prior to departure

  • Cancel any other bills/services that you haven’t finished yet (cell phone, Internet, cable, renter’s insurance, etc.)
  • Pack your bags for your trip

Get on the plane and go!


RTW Guide - Table of Contents