If you’re like me, then you’re already dreaming of your next trip! 

Maybe it’s to an exotic island, or to a ski resort in the mountains. Wherever your next adventure takes you, I want to help get you there!

Planning a trip can be overwhelming at times, so I’m here to help you make the most out of this stage. 

In this post, I’ll be sharing my top steps for planning the best trip including planning the logistics, common pitfalls, and how I use a decision matrix to choose my next destination.

If you’re still feeling overwhelmed, consider having me plan your custom trip! Learn more here.

Delta Lake, Wyoming

Common Pitfalls of Trip Planning

When I hear about people planning their next vacation, I find they often fall into one of these common pitfalls. 

1. They focus on planning the perfect trip, rather than a great trip.

Perfectionism can ruin the best intentions and can sometimes cause you to give up on planning all together. 

2. They think they have to plan everything.

In reality, you can plan an amazing and memorable trip without planning every aspect of your day. In fact, keeping things open can bring the best travel moments. 

1. They try to please everyone.

If you’re planning to travel with a large group, it can be tempting to want to plan group activities for the entire trip, but often that causes tension and dissatisfaction.

Instead, encourage everyone to do their own thing for part of the day and come back for a group gathering.

For example, plan a free morning and then a group dinner. 

Read More: How to Plan a Trip from Start to Finish

What Are Your Travel Goals?

One aspect of planning a trip that is often overlooked is to start with the WHY. 

Ask yourself these questions when planning your next trip. 

  1. Why do I want to take this trip?
  2. What am I needing right now?
  3. What am I hoping to get out of this trip? 

Answering these questions can be incredibly helpful when planning a trip because it sets the tone for the next steps and details. 

If you aren’t quite sure what your travel goals are then you run the risk of coming home feeling unsatisfied because you didn’t get out of the trip what you wanted or needed. 

Maine – my home state!

Planning the Logistics

This might seem obvious but determining the logistics of your trip is an essential early step in the planning process. 

Decide Who is Going to Come On This Trip

More importantly, who do I want and perhaps don’t want to come on this trip?

The people you travel with can make or break your trip.

Decide the Best Time To Travel

    If at all possible, stay as open as possible. Even if you know you have to travel due to your kid’s school schedule, keep the dates flexible. 

    Decide Where You’ll Go!

    Choosing where to go is one of the best and most overwhelming parts of travel planning!

    Just like the timing of your trip, if you can remain flexible with which destination you choose, you open yourself up to more possibilities and sometimes huge savings. 

        We’ll talk about how to choose a destination using a decision matrix below!

        Grand Teton National Park, Wyoming

        Decide How You’ll Pay for This Trip

        There’s nothing worse than coming home from a vacation only to have to keep paying for it.

        When possible, set up a savings fund just for vacation. Contribute a set amount each paycheck.

        Then when you’re ready to take your trip, you’ll have $$ in the bank!

        Setting an agreed upon budget when traveling with multiple parties is essential.

        It’s not a super fun conversation, but it’s vital if you don’t want hurt feelings or miscommunication while on your vacation. 

        Decide Who Will Plan the Trip

        Not everyone loves to plan their travels. I know, it shocked me too! 

        But the great thing is, usually there’s at least one person in every travel party who thrives on planning. 

        If this isn’t you or perhaps you’re trying to plan the trip for someone else but dreading the process, consider hiring out the planning process. 

        You can go to a travel agent who may or may not charge fees, but they will usually stick you with the brands, experiences that they get a cut from. 

        OR you can hire an independent third party, like me! I send you a quick survey about your travel preferences and wants and within a few weeks you get a custom trip plan! 

        No matter which direction you choose, the process of planning a trip should be fun, not stressful. 

          Narrow Down Possible Destinations with a Decision Matrix

          One handy tool I like to use is a decision matrix. This is a nerdy, but very helpful tool to help you make decisions. 

          How does it work?

          List your destination options on one side.

          Next, list the destination components that are most important to you on top. 

          For each destination you will give the components a score from 1-5 (5 being the best score). 

          Here’s an example of how I’ve used a decision matrix:

          DestinationKnown for foodAffordableCrowdfreeBeautiful LandscapesGreat hikingTotal Score (highest score wins)
          France5334419
          Aruba3234214
          Iceland2135415

          Based on the scores above, it appears France would be my best next destination. 

          I love using this method because it takes the emotion out of the decision and focuses on what you actually want out of the trip!

          Read More: How to Pick Your Next Memorable Vacation Destination

          Pick What You’ll Do on Vacation

          Once you’ve settled on your destination, it’s time to select what you’ll be doing! 

          Here’s the catch though, less is more! 

          We always overestimate what we can do in one day. And yes, while it may be possible to visit every major attraction in your destination, do you really want to? No! You’ll be exhausted. 

          Instead, I stick to a rule of only planning 1-3 activities per day. 

          Ideally, plan 1-2 activities for the morning, and one in the evening, or something like that!

          The point is to not get so fixated on the activities of your trip that you forget to slow down and savor the experience. 

          This “rule” allows you to see your destination while also being able to experience your destination and leaves room for spontaneity.  

          Rhinebeck, New York

          Final Thoughts

          Whether you decide to visit France, Iceland, the iconic sights of the US, or somewhere no one’s heard of, I hope these steps help plan your trip! 

          Of course there are a few other things you’ll need to do like book accommodation, flights, get visas, etc. But this article should give you a jumping off spot to help get you started. 

          And again, if you’re still dreading the process, I can help!

          Happy Traveling! 

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