How to Plan Travel Like a Pro

Updated: Dec 26, 2019

I may be crazy, but I love planning travel. I love figuring out how lots of little pieces fit together, and how to make the most of my time somewhere. For a lot of other people, however, that is not the case. For many people, planning travel is a nightmare, and may cause more stress than the vacation offers relaxation, defeating the whole point!

Planning travel may make you want to jump off a cliff

Luckily, planning a trip doesn’t have to be so hard. Over many years (and through many, MANY mistakes) I’ve made a Travel Planning Guide for myself that breaks down all of the important components of planning and booking a trip, makes them easy to visualize and see all in one place, and helps prevent you from experiencing disasters like ending up in the wrong country.

Once I am done planning, I end up with a nice calendar containing all of the information I need for my trip: Where I am staying, how I get there, what I should do while I am there, what I should eat, helpful guides and resources, confirmation numbers, and everything else.

I also make sure to plan out some good wine bars!

While I have never ended up in the wrong country, I have ended up in the wrong state – a mistake that I do not want to repeat again soon. Did I mention that the Travel Planning Guide came about through trial and lots of errors? Every time I have made a mistake when planning travel (like booking for the wrong destination), I have looked back at my guide to see where the information was missed, or how I could better present it so that I can understand what I was talking about when I come back to the document later. Each mistake helped make my guide better and more comprehensive.

Yay for better travel planning guides!

Take, for example, my first long international trip with my boyfriend. We spent a lot of time planning every detail of the trip. Both of us are seasoned travelers, so we had no major concerns, and were sure we had done everything properly. That is until we arrived to JFK and were waiting for our flight to Singapore and we got a notification that our flight FROM Singapore was about to board. We both read the alert and were SUPER confused. Why would Air Asia notify us a day early? Why was the date wrong on the notification? What was going on?

Then it hit us… with the time change we were actually going to be losing not just one day to travel, but two. Now we had both traveled to SE Asia before so we both KNEW this, but we didn’t factor in that our overnight flight to Singapore, stopping in Frankfurt, was actually going to cover TWO nights, and arrive 2 calendar days after it took off. So, when we were booking our flight (and our hotel) we only accounted for one night on the plane, meaning we booked everything else, including our next flight, a day too early. ALWAYS double, triple, quadruple check flight departure AND arrival time and date folks.

Luckily, we were quickly able to log online and book new flights, and email the hotel to say that we would be arriving a day late. The hotel ended up graciously allowing us to stay an extra day on the back end of our time in Penang for free (thanks Tien Hotel Residence!) so we just ate the cost of one-way flights from Singapore to Penang (about $155 total), and went about our merry way. Overall this little hiccup didn’t affect our experience in Malaysia, and we both left with the warm glow of a good trip. However my Travel Planning Guide did change its format so that each night is now accounted for and can’t be skipped!

We successfully made it to Penang in the end!

Ready to skip right to the Travel Planning Guide? Click here! You can also keep reading to learn more about my planning process.

The Adventure Expert Travel Planning Guide helps me take trip planning from a vague idea to a detailed itinerary, and I think it can help you do the same. The guide walks you step-by-step through the process that I use when planning my personal travel (which is also similar to the process I use with clients, but a bit scaled back). The process is really simple, and focuses on 4 main activities:


My brainstorming process helps me thing through all of the elements that are important to me in trip planning like what kind of trip I want to have, when I can travel, and how much I want to spend. It also starts the process of checking out what to do in each spot: cities or destinations, fun activities, restaurants, and whatever else you may want to do! Through this process, I ask myself (and any traveling companions!) the following questions:

1. What do I want out of my vacation?

2. Where can I do that?

3. What is my timeline?

4. What destinations from #2 are best to travel to at that time?

5. What is my budget?

6. What destinations from #4 could fit within that budget?

7. What is there to do in each of the remaining destinations?

8. Where do I want to go?

By going through this questions I narrow down the world of possibilities into ones that are right for this trip, and then choose the one I am most excited about.

This planning process could take you on a NYE trip to Tanzania...


By map I don’t literally mean plot the spots on a map, I mean plan out what each day of your travel is going to look like. This can be as vague as just listing a country you will visit, or it can be as specific as including a detailed schedule of your day. The thing I love most about the process that I have developed is that it allows me to have different travel styles every day, every destination, or every trip. When I map out my trip calendar, I include spaces for the following information:

1. Date

2. City

3. Lodging

4. Travel

5. Travel Details

6. Confirmed Activities

7. Potential Activities

8. Miscellaneous

By the end of my mapping process, I have a pretty good idea of where I want to be when, and often even what I want to do while I am there.

... or a cooking tour of Peru...


Now we get into the nitty gritty details - it is time to start booking! Hopefully your calendar is set up so you can easily see what you need to book.

For most trips, I generally book the following things in advance, and in the following order:

1. Flights

2. Ground Transportation

3. Lodging

4. Major Activities

Flights and Ground Transportation are the most important - can I actually get where I want to be on the day I want to be there? You would be shocked at how many times I have laid out my calendar, booked my flights and a hotel, to then find that a train I need only runs two days a week, or the ferry I planned to take stopped running in May. Luckily, I know know to book the transportation components first to ensure that I don't run into these problems later on in the planning process. The only time I would suggest that you deviate from this order is if you are going to a place that requires specific lodging - think like a safari or jungle camp where there are very few options. If that is the case, I would check availability of the lodging, then check availability of transportation, then book both at the same time.

By the end of this process, I have a calendar that includes all of the information that I will need during my trip - hotels, flights, booking numbers, restaurants - you name it. And I will have downloaded it offline for easy access!

...wherever the trip takes you, it will at least take you to the right spot if you follow my Travel Planning Guide!


Hopefully if you follow these steps, and use the free templates provided, you can make travel planning a little easier, and a little less stressful. Now you can be like me and rather than dreading planning your travels, you can get excited about planning (or at least dreaming about!) your next next trip before you even take your next trip!

My last blog post was about why you don’t need a travel advisor, and this one is giving away my method of planning trips. Am I trying to put myself out of a job?

Probably not. I am just trying to share information that I think will help you travel better – whether you plan it yourself or get me to help you.

Don't need a travel planning guide but want more information on how to budget for a trip, what to pack, and destination recommendations? Subscribe to The Adventure Expert Blog to get all of that information, and more, delivered right to your email in upcoming blog posts!

Does travel planning still seem overwhelming? Request a free consultation today to get travel advice with no strings attached!

This post contains affiliate links. I paid full price for the hotel, and am not receiving any benefit from the hotel for advertising them. I will, however, receive a small commission through if you book Tien Hotel through my affiliate link. I will never share links for places that I wouldn't go myself, without explicitly stating why I wouldn't want to go.

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