Travel Planning: 10 Steps to the Perfect Trip

How a Tour Guide Does it

The winter months offer a break for those of us in tourism and for travelers alike. It’s a good time to review what we did last year, clean up travel gear, and plan for the year ahead. At the moment, my staff and I are already planning not only next year, but two years out. Now, you don’t have to do that of course, but since we do, it may be of some help to see how we plan.

I often get requests for travel consultations. A client will come to me with a plan that just needs help, or with almost no idea about what they want to do. It’s my job to ask questions and help travelers narrow down a literal world of choices. I have a process I go through with each client, which is definitely not rocket science, but perhaps my thought process might be helpful for anyone working on travel planning.

Here is my step by step guide to assembling a great trip. A gentle warning: those of you that love a good spreadsheet are going to love this post. The inverse is also true.

Step One: Where Ya Going?

Deciding where you will go on a trip is probably the hardest part. There are a million possibilities so which is right for you? My suggestion is to always start with a list. I’m not a big fan of the “Bucket List” idea, let’s not get death involved in our vacation please. Instead I like to think of it the way I thought about what I’d ask for from Santa as a kid. It’s a travel wish list.

Your first task is to write a list of every place you’ve ever wanted to go. Organize that list in order of how important each destination is to you, and rate each destination based on cost. This will help you evaluate when to prioritize certain trips based on how much money and vacation time you have available.

Write down a separate list of every experience you’ve wanted to have (ie hot air balloon ride, scuba diving, sailing etc) and compare. The intersection of these two lists should give you somewhere to start.

Of course there are other considerations. Who is going with you? When can you go? But if you start with these two lists, you can start to develop a plan of action.

Step Two: When Should You Go?

The when of travel usually depends on schedules, house or babysitters and jobs, but if it didn’t, when would you go? Start with the weather. Google the annual weather chart for your destination and see when there is a temperature that suits you. I personally love sun and heat, but many like the cold. It’s up to you. Spring and Fall, for example, are both good times for most people.

Now that you’ve narrowed down the general season, it’s time to look at what is best within that timeframe. I usually do this by looking at airfares. If airfare is high, that means your destination will likely be crowded. If it’s low, you know you’ll have few crowds and more hotel options. For example, summer flights to Europe are usually expensive at the end of June, but less a month before.

You can narrow your destination and timeframe down even more by comparing hotel prices. The same hotel can vary hundreds of dollars just days apart, which should be a clue about crowds.

Step Three: Make a Budget

International travel used to be only for the well-heeled, but it’s much more accessible these days. I am not kidding when I say that Disneyland is more expensive than Paris which is why my kids are in Europe every summer. US travel is expensive. Making a budget for any trip will help you understand if a trip is realistic, but I say this to encourage you to price out even your wildest travel dreams. You may be surprised to find that an African safari is less than Hawaii.

Once you price out your top picks, it should be clear which is the winner, and you’ll be ready for the fun part.

Step Four: Research

There was a time when this was where I’d tell you to go buy a guidebook, and that’s still pretty good advice. Guidebooks are a mostly non-biased way of wrapping your head around a destination if you know absolutely nothing. I still buy a stack of guidebooks for new tour itineraries and for travel consultations.

The internet will also tell you about where to go, but often the most popular things on Instagram or TikTok are not the best things. My advice here is to ignore the cheesy morsels of content and look for solid travel advice blogs. Yes, there are still some of those around, including mine. Us old-timers in the travel journalism space still care about good tips.

Aside from hard travel research, I enjoy browsing the library to find books about the destination I’m heading to, whether fiction, history, or biography. A book about your destination may open doors to places or activities that would never occur to you. Reading a history will also add meaning to your visit.

Step Five: Book the Basics

The most common question I get is “When should I book airfare?” The answer is now. Once you’ve decided where you’re going and when, do your flight research. This is the first concrete step, and I recommend doing this before booking a hotel. I’d do this first because many cities often have multiple airports, and your flight schedule/arrival airport may dictate where you’ll stay.

In reality, I often don’t book a year in advance, it’s too far. Six months ahead is usually plenty, but there’s no penalty for doing it super early for many airlines. If a cheaper fare becomes available, some airlines will refund you the difference—check this policy before you book. But let’s be real, usually airfares only increase.

After I’ve booked my airfare, it’s time to decide where I’m staying. Hotels, like airlines, usually only get more expensive so booking early is smart. I’ve written about how to pick a hotel here: https://adventureswithsarah.net/choose-great-hotel/