The Ultimate Guide to Travel Planning

How to Plan the Perfect Trip Without Breaking the Bank

Part 1: Getting Started + Choosing a Location & Budget

You have your vacation time saved up, you’ve been slowly adding to the vacation fund, and you’re finally ready to take that vacation you’ve been daydreaming about. But… you have no idea where to start. Don’t panic, you’re not alone. In this ultimate guide to travel planning series, I’ll take you through the ins and outs of travel planning from start to finish. In no time you’ll be on your way to becoming a travel planning expert!

I want to start off by saying this series is pretty thorough. I’m sharing every bit of the travel planning know-how that I’ve amassed over the years with you my fellow travelers to prove that planning your perfect trip doesn’t have to be hard. With a little bit of time and know-how, anyone can be relaxing on a tropical beach in Asia or wandering cobblestone streets in Europe.

First off, hooray for making good use of your vacation time! A shocking 55% of Americans left vacation time unused in 2015. This adds up to 658 million unused vacation days. Gasp!  I am not one of them, and you shouldn’t be either!

While planning a multi-week trip halfway around the world can seem like a daunting task, it doesn’t have to be. Technology is making it easier and more affordable than ever to plan the trip of your dreams. I have compiled a list of great travel resources that I use on a regular basis to help with me plan an epic trip all while saving money on travel. Be sure to take a look, they’ll come in handy! Those resources paired with this start-to-finish travel planning guide will help make your vacation a reality. So, take a deep breath, and let’s get planning.

Start Small

As with any substantial undertaking, don’t focus on every single detail right off the bat. I know I have to tendency to look at everything all at once, freak out about how much I need to do and how little I actually have done, then put it off for another day. Sound familiar? It sounds basic, but it’s always easier to break it down and start small.

The very first thing you need to do is super easy. Create a method to stay organized. I usually start out by creating a folder on my desktop for the vacation I’m about to plan, then open and save a blank Word document in said folder. This can also be done through Google Docs, or the good old fashioned way with a notepad and folder. You need a central place to keep all of your lists, confirmation emails, hotel addresses, activity ideas, itinerary, etc. and don’t want to have to go digging around the house for them. Believe me, I’ve been there, and the folder is a lifesaver.  In addition, choose an email and use it for all of your travel bookings and interactions. It can be one you already have, or you can easily create a new one through Google specifically for your trip.

Choosing A Location & Budget

A great trip can be had at any budget. From a weekend away in Vegas, to an all-inclusive resort in Bali, the options are endless. However, location and budget go hand in hand, and one greatly affects the other, so, before you jump in, you need to first decide a few things:

  • How much do you want to spend?
    What is your initial range for what you want to spend per person? How much do you have saved? What is a reasonable amount you can save per week? Be realistic.
  • What type of trip do I want to have?
    (adventure, solo, tropical, historical, food, art, tour, cruise, etc). This will help you narrow down your locations and what you can afford.
  • How long will the trip be? The distance of the location, your style of travel and the pace your comfortable traveling at will affect both time needed to make the most of that location and budget. If you’re more flexible when it comes to time, 3-7 days in each city usually will suffice. It gives just the right amount of time to see the sites and get in tune with the overall vibe of the destination. If you want to see a lot in a short period of time, you can get away with spending 1-2 days in a location, but plan your time wisely.
  • When do I want to go? There are 3 travel seasons – high, low and shoulder season, with each varying depending on location. High season is typically the “best” time to go with pleasant temperatures, less rain, and is usually summer or during holidays. That being said, it’s the time everyone wants to be there, therefore be prepared for crowds, long lines and higher prices. Low season is typically “off-season” and brings either cooler or very hot temperatures and/or rainy season. One benefit to low season is that lower prices and special offers on flights, accommodations, and activities are easy to find. So, if you don’t mind a little less then desirable weather to save big, this is for you. My personal choice is shoulder season. It’s the time in between high and low season, which usually means still good weather,  slightly less crowds, and decent pricing. It’s the best of both worlds. Decide on a general time of year and go from there.

PRO TIP: When choosing travel dates, keeping them flexible will help you save a bundle.

Travel Planning 101

Santorini, Greece


With a bucket list a mile long, I know how difficult it can be to narrow a destination down, but you can always visit more than one if it’s in the same general area, especially when on a tour or cruise. So don’t be afraid to be a little ambitious with your trip if your the adventurous type, but also be realistic, because it’s impossible to see Rome in one day.

After answering these questions, it’s time to begin researching locations & choose your top 3. The US dollar is super strong right now, but you still have to keep in mind, the location you choose will affect your budget. If you’re looking for a place where the US dollar goes a little further, here’s a great article from Conde Nast Traveler on “10 Places Where The Dollar is Worth the Most.” 

travel planning budget sheet


Once you settle on your destination(s), nail down the budget, doing one for each on your shortlist. I have included a travel budget worksheet to help you tally everything up, which can be downloaded (here). When filling it out, use the high end of the numbers you research. It’s always better to plan for a higher budget and be under than to plan for a lower budget and go over. A quick search on Expedia or Agoda will give you a general idea on hotel prices, Kayak for flight prices, TripAdvisor or Viator for activities, and Yelp or Google for food. Once costs are analyzed and compared, pick your favorite and do a happy dance, because you’re going on vacation!

Where are you going next? 

Stay tuned for part 2 and beyond coming soon!


The Ultimate Guide to Travel Planning