Are you notoriously disorganized? Do you buy all the adorable Anthropolgie planners, but literally never use them? Do you have file organizers upon file organizers with nothing in them? Then this post is for you! I am horrendously disorganized and tend to be on the forgetful side, so planning my summer vacation for the first time without a travel agent (Or my mom) was so daunting. Sometimes life is amazing and offers you a vacation — which for the average guy and gal **Cough Ben and Mary Cough** is a luxury and a rarity. When the gates of glorious vacation open their doors to you, you want to make the most of that magical time and plan something that doesn’t turn out like  Castaway.

Growing up, my mom planned all our vacations down to the tiniest detail. She is an amazing planner, list maker, and vacation organizer. I tried my best to take hints from how I’ve observed her prep for the perfect getaway, and I have condensed that down for those of us who aren’t naturally skilled in the art of organization.

  1. LISTS, LISTS, AND MORE LISTS: This has helped me more than anything! I have a list for every detail of every trip all in one folder. Lists of what to pack, how to pack, where we are going, what activities are available in our destinations in case plans get canceled, what hospitals are near by, who to call if authorities are needed etc. ( I often keep these folders filed away under “Travel” in case I return to the same destination and really loved the airline I used, hotel, Airbnb or just general info that was necessary for a return)
  2. Backup documents: The worst thing that could happen on your trip is to lose any of your important documents. I photo copied everything from our birth certificates to our driver’s licenses in case of loss or theft. I have done this every trip I’ve ever been on, and it gives me the greatest peace of mind when traveling. I keep a folder tucked inside the lining of my suitcase, with photo copies of anything that could be needed. ( Make sure you have an extra set of print outs for any airline tickets, hotel reservations, shore excursions, and travel insurance too!)
  3. Check Legitimacy: This is HUGE, there are so many companies out there, that genuinely want to take your money and run. So make sure no matter who you book with, no matter how reputable, do a thorough google and yelp check to make sure everything is A-OK.
  4. Buy Travel Insurance! This is an absolute must. You never know when your trip could need to be canceled last minute, or your luggage may be lost etc. It’s hugely important to always have some sort of travel insurance plan to fall back on. I don’t recommend buying it through the company you are traveling with (Cruise lines especially!) I would highly recommend getting it through a third party or a trusted travel agent.
  5. Start Simple! Don’t go crazy on your first fully self-planned vacation. If you are disorganized and choose a wild 2-week adventure in a foreign country as your first self-planned vacation, you are far more likely to get bogged down in all the reservations, plane tickets, transfers, car rentals, visa waivers, etc. and things will get messy! Start small. Choose something that is partially planned for you; that way you can get the hang of travel organization in baby steps. Choose a tour set from Groupon that includes flights and hotels booked for you.
  6. Last but not least, Know your budget:  The last thing you want to do is book everything on credit and max yourself out. I promise when you get back home and out of vacation mode, you’ll regret it! You will also likely regret it while on vacation and you have no money to spend at your destination. I know saving up and waiting for a vacation can drive you crazy ( I know it does to me!). There are really amazing apps out there these days specifically designed to help you save up for a dream vacation, and apps designed to help you find the very best deals when you just can’t wait to save and need a getaway NOW! Ben and I have been planning a trip to Japan since we got married, and it’s in our 5-year hopeful goal haha. I recently found this amazing app called Hitlist. With Hitlist you can make a list of places you want to visit in the future, and Hitlist will notify you every time a price drops on bookings for your destination. There is also EveryDollar. EveryDollar is awesome it helps you plan out monthly budgets, tells you how much you have available each month to put into savings, and gives you a projection of how soon you can reach your monetary goal for your vacation.


  •  Just a few tiny sub-tips that may not always apply.
  • Learn a little something about the culture and laws of the place you are visiting. I hear horror stories constantly about people who took photos in an area of a country where it wasn’t legal (and no signs were present) that were subsequently arrested or had their very expensive camera confiscated. 
  • Do a quick check and find out where your Consulate may be in the country you are visiting. This is great in the event of loss of passports or visas, as well as during times of uprising in that country where you may be in danger.
  • Do a little research on hospitals and what medical is like in those countries. Some countries won’t even allow outsiders entry to a hospital without a large sum of money in cash upfront. 
  • Get a travel Cell phone plan! That or purchase a sim card in the country you are visiting. That way you can use your phone worry free of overages if there is an emergency.
  • Get the google photo translate app! It’s extremely helpful if you are going to a foreign country where it’s unlikely anyone will speak English. It can translate everything from street signs to product details on food!
  • Keep in mind that every vacation is a gamble, there is always a chance that things can be canceled and plans will be broken, but don’t let that stop you from exploring!

I know all of these things are lame, and make the week or month prior to vacation super boring, but trust me, you will save yourself so much anxiety if you do this all in advance. I hope these tips help you, whether you are planning a vacation, dreaming a vacation, or just living life and considering what you might do in the future. While it is easiest to live life unorganized, the more prepared you are for everything, the more free time your brain has to notice the little things in life that you might miss while panicking over your that thing you lost that you thought for sure you filed. 


P.S I was not sponsored by or paid by any of the websites, apps, or companies listed in this post.