11 Steps To Booking The Vacation You've Been Dreaming Of

by Clay Winowiecki

The most common question I get asked from my readers and friends isn’t how to save for a trip, but how to PLAN one.

The following isn’t the only way to plan a trip, as everyone has different styles to accomplish doing so, but rather, what I do.

There are many travelers out there who don’t plan at all; they just purchase a ticket to somewhere far away, pack their bags and go. While that’s definitely an adventurous way to travel, it's not for everyone.

So, if you have no idea where to start, read on.

Pick A Destination

The world is an unfathomable place when it comes to size (at least for me) and picking where to travel to next can be among the hardest decisions of all.

What cultures or activities interest you the most? Do you want to go diving off of coral reefs or drive through wine country? Do you want to get lost with a jungle tribe or explore a sprawling city full of top-notch nightlife? Are you looking to spend a lot of money or be as frugal as possible?

Ask yourself a few simple questions to narrow down your list, and then, decide from there.

Maybe you saw a movie, like "The Lord of the Rings," and your secret obsession with it has grown to the point that you need to visit the iconic filming spots. Discover your tastes and own them!

Name Your Date

Now that you know where you want to go, it’s time to decide when you will go. Your destination may not be as exciting during a certain part of the year, so research the best time to go. Once you find the season you like, pick the month.

It’s easier to give yourself a flexible time span to purchase your tickets so you can pick the day that offers the lowest fare.

The middle of the week, early mornings and late evenings are generally the best times to fly.

Choose A Trip Length

Do you want to road trip across the United States, ride a motorcycle across India or just go on a two-week trip to visit all the tourist attractions in Paris?

Deciding how long you plan to stay will give you a good end-point you can look toward for the next step.

Create A Budget

This budget doesn’t have to be very extensive; it's just important that you take all of your available funds you plan to have at the time of departure and budget into categories like, transportation, accommodation, food, alcohol, activities and souvenirs.

A budget will give you a general idea of how much you should spend for every purchase, including your airfare.

Purchase Your Ticket

My favorite part of planning for a trip is buying the ticket. This step sets your trip in stone and allows you to relax a bit more while you wait for the day to come.

If you’re buying a plane ticket, purchase it two to three months out from the date you plan to leave.

Around that time, the airline knows how well the plane is filling up and will adjust the seat prices accordingly; this can save you from overpaying.

Be sure to track the price until your departure, as well. If you notice that the price of your ticket went down after you bought it, you can try to get a refund. It may not work, but occasionally, you can get the difference refunded.

Create A Rough Itinerary

This step is completely optional. Some people don’t like to plan out their trips, but if you do, this is the time to do it.

You can decide what items are absolute musts for you while you’re there, how much they cost and how long they will take.

Feel free to be as detailed as you want with this one, but once you get there, remember it’s okay to stray from your itinerary. Traveling is all about living in the moment and experiencing the city/country for what it is.

Book Your Accommodations

Depending on the trip, I usually only book one or two nights at a time. I’ll buy accommodations for the date I arrive and for the following day, but after that, I like to be able to scope out other places or move on to another place.

I don’t like to hold myself down when I’m traveling.

Buy Travel Insurance

Many people overlook this step, but it’s very important, no matter how small your trip.

When you’re hurt 2,000 miles away from home, you’ll wish you were better prepared. It’s worth the extra cost and it guards against more than just your health.

I know, as a 20-something, my health is generally the last thing I worry about.

If you need some more convincing, insurance can also protect your property and help you when you get lost, depending on your plan. A good company to look up is World Nomads.

Final Preparations

The time has come to set up a plan to take care of your bills, have someone check your mail and watch your house, take care of your pets (if you have any) or sell your items, if you are leaving for a long period of time.

If you do plan on traveling for an extended period of time, you can begin selling your items at step one.

Also, recheck everything for your trip to make sure it is done properly and you won’t have any last-minute surprises.

Stay Inspired

At this point, you’ll probably be beaming with excitement at the thought of your upcoming adventure, but just in case you do need to rekindle any of that inspiration you once felt (or get rid of some nerves), read up on your destination.

Read some of your favorite bloggers' materials if they’ve been there and flip through some guides in a bookstore.

Learn a few useful phrases, in case the destination's population communicates in a different language.


Create a list of everything you need to pack and triple check (yes, triple check!) to make sure you have everything. Organize it all neatly with zip-locked bags, rubber bands and folding, and then start putting items in your pack.

Remember, if you have a big bag, you don’t need to fill it all the way. While doing so will be tempting, only take what you need.

I have a 64-L travel pack and I only carry the necessary clothing/toiletries, a few things so I can keep my blog going, my cell phone and Nook, so I can read.

Before packing anything, ask yourself if you will use it multiple times in a week. If not, don’t bring it.

So, do you now feel more prepared to take on the world and begin your next adventure? I hope so! Good luck on your next trip and happy travels!