How to Plan an Epic Trip

Trip Planning For All Types of Travelers

There are a few common questions I get from friends, family, and other’s on my social media communities, much of which revolve around planning a STELLAR vacation. More specifically,

1. How do you find the time to travel so much with a full-time job?
2. How do you have the money to travel so much?
3. You must be a planner. (OK, I cheated, that isn’t a question – but my gosh do I hear this often… I’m looking at you, Mom)

My goal today is to answer those questions, and to help people who are having a hard time getting out and seeing the world. Everyone’s situation (financial, and otherwise) is different, and everyone’s goals and priorities are different. I tried to remain aware of this, while sharing my process with you.

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Plan Your Trip Early

YES, I am a planner. You know why? Because I thrive when I know what my life is going to look like in both the near and far out future. I also firmly believe I am able to accomplish a GREAT deal more (both in travel, and in work) when I plan ahead.

So, the first step in planning an epic trip is getting a couple of things out of your brain and onto paper.

1. Identify the time of year you can travel (summer and winter travel destinations vary, big time – and you can really avoid peak pricing if you think that through early enough)
2. Identify how much time you can get off work / school / etc. Do you have a week, 2 weeks? This matters! If you are limited on time, you are less likely to spend a chunk of your vacation on a long flight across the world

One thing we struggle with is wanting to travel over the holidays – as this is when both myself and my husband have the most time off – but everything from flights to accommodation is overly expensive. That is why we usually use that time to see family, and then take a trip when less people are traveling, and flights are cheaper in January / February. You might be saying, ‘well I can’t get time off in January when I just took time off in December”. While that might be true, I bet if you planned it early enough, you would be more likely to.

Budget Accordingly & Make Travel a Priority

Your budget is going to depend on a lot of things, but here are a few:

1. How much money do you have to spend
2. How much money do you want to spend
3. How much time did you decide you were going to spend on vacation? Maybe you want to travel to a very expensive destination (Ahem, I’m looking at you Switzerland), and so you are willing to spend less time on vacation to go somewhere a bit pricier
4. How much time do you have until this trip? The longer you give yourself, the more time you have to save accordingly
5. Do you have an opportunity to use points? This is CRITICAL for us

We use both Delta Skymiles and the American Express Platinum card to accumulate both points and miles for our trips. This has been a game changer, as we are basically guaranteed 1 free trip per year (both flights and accommodation covered) with our points accumulation

My husband reminded me to share with all of you that we travel a lot, because we make travel a priority.

Now, there are a lot of things that can get in the way of your dream trip, and trust us, we have faced many of those things (HVAC repairs, dog surgeries, unexpected deployments, etc.) but typically, if we are choosing between a new car, new bedroom furniture, or a vacation, we are choosing the vacation. This might not be your priority, and that is completely fine – I am positive you have good reason to prioritize other things!

Once you decide that travel is going to be a priority, and plan ahead, budget accordingly, set realistic expectations, do your research, and remain flexible, you will find yourself seeing a bit more of the world.

Choose Your Destination – And Be Flexible

Based on how much time you have, and your budget, you can now choose your destination!

Unless you are someone who is DEAD SET on a specific location, and you would do anything to save all of your money and vacation time for that ONE location, BE FLEXIBLE.

My husband and I have a very, very long list of places we want to visit. Remaining flexible in what our next destination will be has allowed us to select our next trip based on what will be most affordable and reasonable given our budget and allotted time off.

Once I know the time of year I want to travel, and the money I plan on spending on the trip, I begin using Google Flight Search to scan for flights. I begin to mark flights costs for a handful of prospective destinations, and track those same destinations with various departure / return dates over the next few weeks. My goal here is to see if flight costs are staying the same, going up, or going down.

I also subscribe to Pomelo Travel – an amazing cheap flight notification list serve.

Pomelo sends me cheap flight alerts daily, to destinations around the world. My current settings allow me to receive these alerts for departures from all US airports, but you are able to adjust your settings to select home airport(s) to customize your alerts. I want to make it super clear – that while you can click typically book directly through the email, I use this more or less as a notification/alert system, and then book my travel through American Express Travel and Delta Airlines (if possible) to secure my points.

True story – A couple of years ago, we knew we had a couple of weeks off, 4 months away. I laid out a rough budget, and rough dates, and began flight scanning. I got an email a few days later from Pomelo Travel about a new, cheap flight path to the Azores Islands. Though we had never heard of the destination, we did some research and within 24 hours, pulled the trigger and booked the trip. It was the best trip of our lives.

Do Your Research & Use Multiple Sources and Platforms

This step typically starts once I have narrowed down my destination search to 1-3 locations. I begin researching what exactly we could do at each destination given the amount of time and budget we have. We like to start our trips with something big (summiting a mountain, learning something new (to ski, or rock climb), or attending a big event). After that, it’s about covering a lot of ground and seeing / doing as much as possible.

Over the past several years I have largely used social media (primarily Instagram) , and travel blogs, to research my trip destinations.

DISCLAIMER: A lot of social media and travel blog material is curated – so make sure you are (1) maintaining realistic expectations, (2) finding information from more than a handful of sources, and (3) following those who are genuine and honest about their travel experiences.

On Instagram I search hashtags and location pins, I watch stories that pinned the location(s) I am interested in, and I often private message individuals or organizations that posted the content to inquire more about their experience.

I use WordPress reader, and conduct a simple Google search to look for travel blogs that provide itineraries, ‘must do’ lists, and that ultimately keep it real about their experiences. As with Instagram, I often comment on the blog post, or send an email following up with additional questions about their experiences.

I think coming up with a bullet point list of things to do in each location, along with a rough idea of price for each item, is very helpful in narrowing down which destination makes sense for this next trip. Again – I think it can be very helpful to travel in the ‘off season’ to certain destinations.

Example: Go to Switzerland in between holidays, and during a ‘non-peak’ season based on their ski pass prices.

If You Can, Plan Around a Work Trip

This is definitely not going to apply to everyone – but for those who travel for work, this can be incredibly beneficial.

Both myself and my husband travel often for work, and we try to take every opportunity to tag a trip onto the end of a work trip. For example – I was living and working in Kenya, and my work was paying for my flight back to America already – so I just added a 1 week layover in Morocco (no cost difference for work) and had my husband meet me there. That way, we only had to pay out of pocket for 1 flight to Morocco.

Similarly, I have met my husband in Europe on his way back from a deployment. Again, only absorbing the cost of 1 plane ticket.

Start Small – If It Helps

If you are someone who has seldom traveled within your own country, let alone internationally, start small! Go on a road trip, fly to a domestic destination for a weekend, visit a friend in a far-off town!

My blog has mostly highlighted international travel – but I have taken countless smaller trips! In fact, most of my travel in my early 20’s was within the United States, and by car at that! It was cheaper, easier, and all around more feasible to plan and execute a weekend getaway a few states away. Do that until you feel comfortable to spread your wings abroad!

Not everyone is ready to take a solo trip across East Asia as their first big vacation – so it’s perfectly OK if you need to take a few smaller trips to get your feet under you enough to plan a bigger trip!

Ask For Guidance

This goes hand in hand with doing your research – but don’t be afraid to ask questions! Travel writers, like myself, literally live for a good travel-related conversation. Trust me, if you write me asking my advice on a certain budget, or destination, I will be thrilled.

It is a win-win for both of us, so don’t be afraid to ask!

Lastly, HAVE FUN WITH IT – Travel is one of the greatest gifts we can give ourselves!